U.S. patent application number 17/489499 was filed with the patent office on 2022-04-28 for compound for organic electronic element, organic electronic element using the same, and an electronic device thereof.
This patent application is currently assigned to DUK SAN NEOLUX CO., LTD.. The applicant listed for this patent is DUK SAN NEOLUX CO., LTD.. Invention is credited to Jae Wan Jang, In Goo Lee, Nam Geol Lee, Sun-Hee Lee, Yun Suk Lee, Soung Yun Mun, Jonggwang Park, Jae Duk Yoo.
Application Number | 20220131091 17/489499 |
Document ID | / |
Family ID | |
Filed Date | 2022-04-28 |
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United States Patent
Application |
20220131091 |
Kind Code |
A1 |
Lee; Yun Suk ; et
al. |
April 28, 2022 |
COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT
USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
Abstract
Provided are a compound of Formula (1) for use in an organic
electronic element and capable of improving the luminous
efficiency, stability and lifespan of the organic electronic
element, an organic electronic element employing the compound, and
an electronic device thereof.
Inventors: |
Lee; Yun Suk; (Cheonan-si,
KR) ; Lee; Nam Geol; (Cheonan-si, KR) ; Jang;
Jae Wan; (Cheonan-si, KR) ; Yoo; Jae Duk;
(Cheonan-si, KR) ; Mun; Soung Yun; (Cheonan-si,
KR) ; Park; Jonggwang; (Cheonan-si, KR) ; Lee;
Sun-Hee; (Cheonan-si, KR) ; Lee; In Goo;
(Cheonan-si, KR) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
DUK SAN NEOLUX CO., LTD. |
Cheonan-si |
|
KR |
|
|
Assignee: |
DUK SAN NEOLUX CO., LTD.
Cheonan-si
KR
|
Appl. No.: |
17/489499 |
Filed: |
September 29, 2021 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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17212886 |
Mar 25, 2021 |
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17489499 |
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17096790 |
Nov 12, 2020 |
11063226 |
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17212886 |
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International
Class: |
H01L 51/00 20060101
H01L051/00 |
Foreign Application Data
Date |
Code |
Application Number |
Oct 26, 2020 |
KR |
10-2020-0139441 |
Claims
1. A compound represented by Formula (1): ##STR00068## wherein: 1)
Ar.sub.1 and Ar.sub.2 are each independently a C.sub.6-C.sub.18
aryl group; or a C.sub.6-C.sub.18 aryl group substituted with
deuterium; 2) R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and
R.sup.6 are the same or different from each other, and
independently of each other are hydrogen or deuterium; and 3) a is
an integer of 0 to 7, b is an integer of 0 to 6.
2. The compound of claim 1, wherein the compound represented by
Formula (1) is represented by Formula (1-1) or Formula (1-2):
##STR00069## wherein Ar.sub.1, Ar.sub.2, R.sup.1, R.sup.2, R.sup.3,
R.sup.4, R.sup.5, R.sup.6, a and b are the same as defined in claim
1.
3. The compound of claim 1, wherein Ar.sub.1 or Ar.sub.2 is
represented by one of the following compounds: ##STR00070##
wherein: 1) R.sup.1, R.sup.2 and a are the same as defined in claim
1, 2) a' and b' are independently of each other an integer of 0 to
5, a'' is an integer of 0 to 4, and 3) * means the bonding
position.
4. The compound of claim 1, wherein a reorganization energy value
of the compound of Formula (1) is less than 0.190.
5. The compound of claim 1, wherein a reorganization energy value
of the compound of Formula (1) is 0.155 to 0.170.
6. The compound of claim 1, wherein the compound of Formula (1) is
selected from the group consisting of compounds P-1 to P-64:
##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075##
##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080##
##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085##
##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090##
##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095##
##STR00096## ##STR00097## ##STR00098##
7. An organic electronic element comprising a first electrode, a
second electrode, and an organic material layer formed between the
first electrode and the second electrode, wherein the organic
material layer comprises an emitting layer, a hole blocking layer
and an electron transport layer, wherein the emitting layer, the
hole blocking layer or the electron transport layer comprises a
compound represented by Formula (1) of claim 1.
8. The organic electronic element of claim 7, wherein the emitting
layer comprises a compound represented by Formula (1).
9. The organic electronic element of claim 7, wherein the emitting
layer comprises a first host compound; and a second host compound;
wherein the first host compound or the second host compound
comprises a compound represented by Formula (1).
10. The organic electronic element of claim 7, further comprising a
light efficiency enhancing layer formed on one surface of the first
electrode and/or one surface of the second electrode not in contact
with the organic material layer.
11. The organic electronic element of claim 7, wherein the organic
material layer includes 2 or more stacks including a hole transport
layer, an emitting layer, and an electron transport layer
sequentially formed on the first electrode.
12. The organic electronic element of claim 11, wherein the organic
material layer further comprises a charge generating layer formed
between the 2 or more stacks.
13. An electronic device comprising: a display device including the
organic electronic element of claim 7; and a control unit for
driving the display device.
14. The organic electronic element of claim 13, wherein the organic
electronic element is any one of an organic electroluminescent
device (OLED), an organic solar cell, an organic photoreceptor
(OPC), an organic transistor (organic TFT), and an element for
monochromic or white illumination.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application is a Continuation-in-Part of U.S. patent
application Ser. No. 17/212,886, filed on Mar. 25, 2021, which was
a Continuation of U.S. patent application Ser. No. 17/096,790,
filed on Nov. 12, 2020, now U.S. Pat. No. 11,063,226, issued on
Jul. 13, 2021, which claims priority to and the benefit of Korean
Patent Application No. 10-2020-0139441, filed on Oct. 26, 2020, the
disclosure of which is incorporated herein by reference in its
entirety.
BACKGROUND
Technical Field
[0002] The present invention relates to a compound for an organic
electronic element, an organic electronic element using the same,
and an electronic device thereof.
Background Art
[0003] In general, organic light emitting phenomenon refers to a
phenomenon that converts electric energy into light energy by using
an organic material. An organic electronic element using an organic
light emitting phenomenon usually has a structure including an
anode, a cathode, and an organic material layer interposed
therebetween. Here, in order to increase the efficiency and
stability of the organic electronic element, the organic material
layer is often composed of a multi-layered structure composed of
different materials, and for example, may include a hole injection
layer, a hole transport layer, an emitting layer, an electron
transport layer, an electron injection layer and the like.
[0004] A material used as an organic material layer in an organic
electronic element may be classified into a light emitting material
and a charge transport material, such as a hole injection material,
a hole transport material, an electron transport material, an
electron injection material and the like depending on its function.
And the light emitting material can be classified into a high
molecular weight type and a low molecular weight type according to
the molecular weight, and according to the light emission
mechanism, it can be classified into a fluorescent material derived
from a singlet excited state of an electron and a phosphorescent
material derived from a triplet excited state of an electron. Also,
the light emitting material may be divided into blue, green, and
red light emitting materials and yellow and orange light emitting
materials necessary for realizing a better natural color according
to the emission color.
[0005] However, when only one material is used as a light emitting
material, due to intermolecular interaction, the maximum emission
wavelength shifts to a longer wavelength, and there are problems in
that the color purity is lowered or the device efficiency is
reduced due to the emission attenuation effect, therefore in order
to increase color purity and increase luminous efficiency through
energy transfer, a host/dopant system may be used as a light
emitting material. The principle is that when a small amount of a
dopant having a smaller energy band gap than that of the host
forming the emitting layer is mixed in the emitting layer, excitons
generated in the emitting layer are transported to the dopant to
emit light with high efficiency. At this time, since the wavelength
of the host moves to the wavelength band of the dopant, light
having a desired wavelength can be obtained according to the type
of dopant used.
[0006] Currently, the portable display market is a large-area
display, and the size thereof is increasing, and thus, more power
consumption than the power consumption required for the existing
portable display is required. Therefore, power consumption has
become a very important factor for a portable display having a
limited power supply such as a battery, and the problem of
efficiency and lifespan must also be solved.
[0007] Efficiency, lifespan, and driving voltage are related to
each other, and when the efficiency is increased, the driving
voltage is relatively decreased, and as the driving voltage is
decreased, crystallization of organic materials due to Joule
heating generated during driving decreases, and consequently, the
lifespan tends to increase. However, the efficiency cannot be
maximized simply by improving the organic material layer. This is
because, when the energy level and T1 value between each organic
material layer, and the intrinsic properties (mobility, interfacial
properties, etc.) of materials are optimally combined, long
lifespan and high efficiency can be achieved at the same time.
[0008] Therefore, while delaying the penetration and diffusion of
metal oxide from the anode electrode (ITO) into the organic layer,
which is one of the causes of shortening the lifespan of the
organic electronic element, it should have stable characteristics
against Joule heating generated during device driving, and OLED
devices are mainly formed by a deposition method, and it is
necessary to develop a material that can withstand a long time
during deposition, that is, a material with strong heat
resistance.
[0009] In other words, in order to fully exhibit the excellent
characteristics of an organic electronic element, the material
constituting the organic material layer in the device, such as a
hole injection material, a hole transport material, a light
emitting material, an electron transport material, an electron
injection material, etc., is supported by a stable and efficient
material and should take precedence, but the development of a
stable and efficient organic material layer material for an organic
electronic device has not yet been sufficiently made. Therefore,
the development of new materials is continuously required, and in
particular, the development of a host material for the emitting
layer is urgently required.
DETAILED DESCRIPTION OF THE INVENTION
Summary
[0010] In order to solve the problems of the above-mentioned
background art, the present invention has revealed a compound
having a novel structure, and when this compound is applied to an
organic electronic element, it has been found that the luminous
efficiency, stability and lifespan of the device can be
significantly improved.
[0011] Accordingly, an object of the present invention is to
provide a novel compound, an organic electronic element using the
same, and an electronic device thereof.
Technical Solution
[0012] The present invention provides a compound represented by
Formula (1):
##STR00001##
[0013] In another aspect, the present invention provides an organic
electronic element comprising the compound represented by Formula
(1) and an electronic device thereof.
Effects of the Invention
[0014] By using the compound according to the present invention,
high luminous efficiency, low driving voltage and high heat
resistance of the device can be achieved, and color purity and
lifespan of the device can be greatly improved.
BRIEF DESCRIPTION OF THE DRAWINGS
[0015] FIG. 1 to FIG. 3 each illustrate an exemplary view of an
organic electroluminescent device according to the present
invention.
TABLE-US-00001 [0016] The numbers in the drawings indicates: 100,
200, 300: organic electronic 110: the first electrode element 120:
hole injection layer 130: hole transport layer 140: emitting layer
150: electron transport layer 160: electron injection layer 170:
second electrode 180: light efficiency enhancing Layer 210: buffer
layer 220: emitting-auxiliary layer 320: first hole injection layer
330: first hole transport layer 340: first emitting layer 350:
first electron transport layer 360: first charge generation layer
361: second charge generation layer 420: second hole injection
layer 430: second hole transport layer 440: second emitting layer
450: second electron transport layer CGL: charge generation layer
ST1: first stack ST2: second stack
DETAILED DESCRIPTION
[0017] Hereinafter, some embodiments of the present invention will
be described in detail. Further, in the following description of
the present invention, a detailed description of known functions
and configurations incorporated herein will be omitted when it may
make the subject matter of the present invention rather
unclear.
[0018] In addition, terms, such as first, second, A, B, (a), (b) or
the like may be used herein when describing components of the
present invention. Each of these terminologies is not used to
define an essence, order or sequence of a corresponding component
but used merely to distinguish the corresponding component from
other component(s). It should be noted that if a component is
described as being "connected", "coupled", or "connected" to
another component, the component may be directly connected or
connected to the other component, but another component may be
"connected", "coupled" or "connected" between each component.
[0019] As used in the specification and the accompanying claims,
unless otherwise stated, the following is the meaning of the term
as follows.
[0020] Unless otherwise stated, the term "halo" or "halogen", as
used herein, includes fluorine, bromine, chlorine, or iodine.
[0021] Unless otherwise stated, the term "alkyl" or "alkyl group",
as used herein, has a single bond of 1 to 60 carbon atoms, and
means saturated aliphatic functional radicals including a linear
alkyl group, a branched chain alkyl group, a cycloalkyl group
(alicyclic), an cycloalkyl group substituted with a alkyl or an
alkyl group substituted with a cycloalkyl.
[0022] Unless otherwise stated, the term "alkenyl" or "alkynyl", as
used herein, has double or triple bonds of 2 to 60 carbon atoms,
but is not limited thereto, and includes a linear or a branched
chain group.
[0023] Unless otherwise stated, the term "cycloalkyl", as used
herein, means alkyl forming a ring having 3 to 60 carbon atoms, but
is not limited thereto.
[0024] Unless otherwise stated, the term "alkoxyl group", "alkoxy
group" or "alkyloxy group", as used herein, means an oxygen radical
attached to an alkyl group, but is not limited thereto, and has 1
to 60 carbon atoms.
[0025] Unless otherwise stated, the term "aryloxyl group" or
"aryloxy group", as used herein, means an oxygen radical attached
to an aryl group, but is not limited thereto, and has 6 to 60
carbon atoms.
[0026] The terms "aryl group" and "arylene group" used in the
present invention have 6 to 60 carbon atoms, respectively, unless
otherwise specified, but are not limited thereto. In the present
invention, an aryl group or an arylene group means a single ring or
multiple ring aromatic, and includes an aromatic ring formed by an
adjacent substituent joining or participating in a reaction.
[0027] For example, the aryl group may be a phenyl group, a
biphenyl group, a fluorenyl group, or a spirofluorene group.
[0028] The prefix "aryl" or "ar" means a radical substituted with
an aryl group. For example, an arylalkyl may be an alkyl
substituted with an aryl, and an arylalkenyl may be an alkenyl
substituted with aryl, and a radical substituted with an aryl has a
number of carbon atoms as defined herein.
[0029] Also, when prefixes are named subsequently, it means that
substituents are listed in the order described first. For example,
an arylalkoxy means an alkoxy substituted with an aryl, an
alkoxylcarbonyl means a carbonyl substituted with an alkoxyl, and
an arylcarbonylalkenyl also means an alkenyl substituted with an
arylcarbonyl, wherein the arylcarbonyl may be a carbonyl
substituted with an aryl.
[0030] Unless otherwise stated, the term "heterocyclic group", as
used herein, contains one or more heteroatoms, but is not limited
thereto, has 2 to 60 carbon atoms, includes any one of a single
ring or multiple ring, and may include heteroaliphadic ring and
heteroaromatic ring. Also, the heterocyclic group may also be
formed in conjunction with an adjacent group.
[0031] Unless otherwise stated, the term "heteroatom", as used
herein, represents at least one of N, O, S, P, or Si.
[0032] Also, the term "heterocyclic group" may include a ring
including SO.sub.2 instead of carbon consisting of cycle. For
example, "heterocyclic group" includes the following compound.
##STR00002##
[0033] Unless otherwise stated, the term "fluorenyl group" or
"fluorenylene group", as used herein, means a monovalent or
divalent functional group, in which R, R' and R'' are all hydrogen
in the following structures, and the term "substituted fluorenyl
group" or "substituted fluorenylene group" means that at least one
of the substituents R, R', R'' is a substituent other than
hydrogen, and include those in which R and R' are bonded to each
other to form a spiro compound together with the carbon to which
they are bonded.
##STR00003##
[0034] The term "spiro compound", as used herein, has a `spiro
union`, and a spiro union means a connection in which two rings
share only one atom. At this time, atoms shared in the two rings
are called `spiro atoms`, and these compounds are called
`monospiro-`, `di-spiro-` and `tri-spiro-`, respectively, depending
on the number of spiro atoms in a compound.
[0035] Unless otherwise stated, the term "aliphatic", as used
herein, means an aliphatic hydrocarbon having 1 to 60 carbon atoms,
and the term "aliphatic ring", as used herein, means an aliphatic
hydrocarbon ring having 3 to 60 carbon atoms.
[0036] Unless otherwise stated, the term "ring", as used herein,
means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic
ring having 6 to 60 carbon atoms, or a hetero ring having 2 to 60
carbon atoms, or a fused ring formed by the combination of them,
and includes a saturated or unsaturated ring.
[0037] Other hetero compounds or hetero radicals other than the
above-mentioned hetero compounds include, but are not limited
thereto, one or more heteroatoms.
[0038] Also, unless expressly stated, as used herein, "substituted"
in the term "substituted or unsubstituted" means substituted with
one or more substituents selected from the group consisting of
deuterium, halogen, an amino group, a nitrile group, a nitro group,
a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxyl group, a
C.sub.1-C.sub.20 alkylamine group, a C.sub.1-C.sub.20 alkylthiopen
group, a C.sub.6-C.sub.20 arylthiopen group, a C.sub.2-C.sub.20
alkenyl group, a C.sub.2-C.sub.20 alkynyl group, a C.sub.3-C.sub.20
cycloalkyl group, a C.sub.6-C.sub.20 aryl group, a C.sub.6-C.sub.20
aryl group substituted by deuterium, a C.sub.8-C.sub.20 arylalkenyl
group, a silane group, a boron group, a germanium group, and a
C.sub.2-C.sub.20 heterocyclic group, but is not limited to these
substituents.
[0039] Also, unless there is an explicit explanation, the formula
used in the present invention is the same as the definition of the
substituent by the exponent definition of the following
formula.
##STR00004##
[0040] Here, when a is an integer of zero, the substituent IV is
absent, when a is an integer of 1, the sole substituent IV is
linked to any one of the carbon constituting the benzene ring, when
a is an integer of 2 or 3, each is combined as follows, where IV
may be the same or different from each other, when a is an integer
of 4 to 6, it is bonded to the carbon of the benzene ring in a
similar manner, while the indication of the hydrogen bonded to the
carbon forming the benzene ring is omitted.
##STR00005##
[0041] Hereinafter, a compound according to an aspect of the
present invention and an organic electronic element including the
same will be described.
[0042] The present invention provides a compound represented by
Formula (1):
##STR00006##
wherein: 1) Ar.sub.1 and Ar.sub.2 are each independently of a
C.sub.6-C.sub.18 aryl group; or a C.sub.6-C.sub.18 aryl group
substituted with deuterium; 2) R.sup.1, R.sup.2, R.sup.3, R.sup.4,
R.sup.5 and R.sup.6 are the same or different from each other, and
independently of each other are hydrogen or deuterium; 3) a is an
integer of 0 to 7, b is an integer of 0 to 6.
[0043] Also, the present invention provides a compound in which
Formula (1) is represented by Formula (1-1) or Formula (1-2):
##STR00007##
[0044] Wherein Ar.sub.1, Ar.sub.2, R.sup.1, R.sup.2, R.sup.3,
R.sup.4, R.sup.5, R.sup.6, a and b are the same as defined
above.
[0045] Also, the present invention provides a compound in which
Ar.sub.1 or Ar.sub.2 is represented by any one of the above
compounds:
##STR00008##
wherein 1) R.sup.1, R.sup.2 and a are the same as defined above, 2)
a' and b' are independently of each other an integer from 0 to 5,
a'' is an integer from 0 to 4, 3) * means the bonding position.
[0046] Also, the present invention provides a compound having a
reorganization energy value of less than 0.190 of the compound
represented by Formula (1).
[0047] Also, the present invention provides a compound having a
reorganization energy value of 0.155 to 0.170 of the compound
represented by Formula (1).
[0048] Also, the present invention provides a compound in which the
compound represented by Formula (1) is represented by any one of
the following compounds P-1 to P-64:
##STR00009## ##STR00010## ##STR00011## ##STR00012## ##STR00013##
##STR00014## ##STR00015## ##STR00016## ##STR00017## ##STR00018##
##STR00019## ##STR00020## ##STR00021## ##STR00022## ##STR00023##
##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028##
##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033##
##STR00034## ##STR00035## ##STR00036##
[0049] Referring to FIG. 1, the organic electronic element (100)
according to the present invention includes a first electrode
(110), a second electrode (170), and an organic material layer
including a single compound or 2 or more compounds represented by
Formula (1) between the first electrode (110) and the second
electrode (170). In this case, the first electrode (110) may be an
anode, and the second electrode (170) may be a cathode. In the case
of an inverted type, the first electrode may be a cathode and the
second electrode may be an anode.
[0050] The organic material layer may sequentially include a hole
injection layer (120), a hole transport layer (130), an emitting
layer (140), an electron transport layer (150), and an electron
injection layer (160) on the first electrode (110). In this case,
the remaining layers except for the emitting layer (140) may not be
formed. It may further include a hole blocking layer, an electron
blocking layer, an emitting auxiliary layer (220), a buffer layer
(210), etc. and the electron transport layer (150) and the like may
serve as a hole blocking layer. (See FIG. 2)
[0051] Also, the organic electronic element according to an
embodiment of the present invention may further include a
protective layer or a light efficiency enhancing layer (180). The
light efficiency enhancing layer may be formed on one of both
surfaces of the first electrode not in contact with the organic
material layer or on one of both surfaces of the second electrode
not in contact with the organic material layer. The compound
according to an embodiment of the present invention applied to the
organic material layer may be used as a host or dopant of the hole
injection layer (120), the hole transport layer (130), the emitting
auxiliary layer (220), electron transport auxiliary layer, the
electron transport layer (150), and an electron injection layer
(160), the emitting layer (140) or as a material for the light
efficiency enhancing layer. Preferably, for example, the compound
according to Formula (1) of the present invention may be used as a
host material of the emitting layer, a hole blocking layer or an
electron transport layer.
[0052] The organic material layer may include 2 or more stacks
including a hole transport layer, an emitting layer and an electron
transport layer sequentially formed on the anode, further include a
charge generation layer formed between the 2 or more stacks (see
FIG. 3).
[0053] Otherwise, even with the same core, the band gap, electrical
characteristics, interface characteristics, etc. may vary depending
on which position the substituent is bonded to, therefore the
choice of core and the combination of sub-substituents bound
thereto are also very important, and in particular, when the
optimal combination of energy levels and T1 values and unique
properties of materials (mobility, interfacial characteristics,
etc.) of each organic material layer is achieved, a long lifespan
and high efficiency can be achieved at the same time. The organic
electroluminescent device according to an embodiment of the present
invention may be manufactured using a PVD (physical vapor
deposition) method. For example, depositing a metal or a metal
oxide having conductivity or an alloy thereof on a substrate to
form an anode, and after forming an organic material layer
including the hole injection layer (120), the hole transport layer
(130), the emitting layer (140), the electron transport layer (150)
and the electron injection layer (160) thereon, it can be prepared
by depositing a material that can be used as a cathode thereon.
[0054] Also, in the present invention, the organic material layer
is formed by any one of a spin coating process, a nozzle printing
process, an inkjet printing process, a slot coating process, a dip
coating process, and a roll-to-roll process, and the organic
material layer provides an organic electric element comprising the
compound as an electron transport material.
[0055] As another specific example, the same or different compounds
of the compound represented by Formula (1) are mixed and used in
the organic material layer.
[0056] Also, the present invention provides an emitting layer
composition comprising the compound represented by Formula (1), and
provides an organic electronic element comprising the emitting
layer.
[0057] Also, the present invention provides a hole blocking layer
composition comprising the compound represented by Formula (1), and
provides an organic electronic element comprising the hole blocking
layer.
[0058] Also, the present invention provides an electron transport
layer composition comprising the compound represented by Formula
(1), and provides an organic electronic element comprising the
electron transport layer.
[0059] Also, the present invention provides an electronic device
comprising a display device including the organic electronic
element; and a control unit for driving the display device;
[0060] In another aspect, the organic electronic element is at
least one of an organic electroluminescent device, an organic solar
cell, an organic photoreceptor, an organic transistor, and a device
for monochromatic or white lighting. At this time, the electronic
device may be a current or future wired/wireless communication
terminal, and covers all kinds of electronic devices including
mobile communication terminals such as mobile phones, a personal
digital assistant (PDA), an electronic dictionary, a
point-to-multipoint (PMP), a remote controller, a navigation unit,
a game player, various kinds of TVs, and various kinds of
computers.
[0061] Hereinafter, a synthesis example of the compound represented
by Formula (1) of the present invention and a manufacturing example
of an organic electronic element of the present invention will be
described in detail with reference to Examples, but the present
invention is not limited to the following Examples.
Synthesis Examples
[0062] The compound (final products) represented by Formula (1)
according to the present invention is synthesized by reacting Sub 1
and Sub 2 as shown in Scheme 1 below, but is not limited
thereto.
##STR00037##
I. Synthesis of Sub 1
[0063] Sub 1 of Reaction Scheme 1 may be synthesized by the
reaction route of Reaction Scheme 2 below, but is not limited
thereto.
##STR00038##
[0064] Synthesis examples of specific compounds belonging to Sub 1
are as follows.
1. Synthesis Example Sub 1-1
##STR00039##
[0065] (1) Synthesis of Sub 1-1b
[0066] naphthalen-2-ylboronic acid (23.9 g, 0.14 mol),
Pd(PPh.sub.3).sub.4 (6.1 g, 0.005 mol), NaOH (21 g, 0.52 mol), THF
(350 mL) and water (115 mL) were added to Sub 1-1a (50 g, 0.17
mol), and the reaction was conducted at 70.degree. C. for 6
hours.
[0067] When the reaction is completed, the temperature of the
reactant is cooled to room temperature, and the solvent is removed.
Then, the concentrated reactant was separated using a silica gel
column or recrystallization method to obtain 48 g (82.4%) of the
product Sub 1-1b.
(2) Synthesis of Sub 1-1
[0068] Sub 1-1b (30 g, 0.09 mol),
1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (29.7
g, 0.09 mol), Pd(PPh.sub.3).sub.4 (3.1 g, 0.003 mol), NaOH (10.8 g,
0.27 mol), THF (180 mL) and water (60 mL) were added, and the
reaction was carried out at 70.degree. C. for 6 hours. When the
reaction is completed, the temperature of the reactant is cooled to
room temperature, and the solvent is removed. Then, the
concentrated reactant was separated using a silica gel column or
recrystallization method to obtain 33 g (80.4%) of the product Sub
1-33.
2. Synthesis Example Sub 1-5
##STR00040##
[0069] (1) Synthesis of Sub 1-5b
[0070] (naphthalen-2-yl-d7)boronic acid (24.5 g, 0.14 mol),
Pd(PPh.sub.3).sub.4 (4.8 g, 0.004 mol), NaOH (16.4 g, 0.41 mol),
THF (280 mL) and water (90 mL) were added to Sub 1-5a (40 g, 0.14
mol), and the reaction was conducted at 70.degree. C. for 6 hours.
When the reaction was completed, 35 g (73.8%) of the product Sub
1-5b was obtained by using the separation method of Sub 1-1b
described above.
(2) Synthesis of Sub 1-5
[0071] Sub 1-5b (35 g, 0.10 mol),
1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (33.4
g, 0.10 mol), Pd(PPh.sub.3).sub.4 (3.5 g, 0.003 mol), NaOH (12.1 g,
0.30 mol), THF (200 mL) water (70 mL) were added, and the reaction
was carried out at 70.degree. C. for 6 hours. When the reaction is
completed, the temperature of the reactant is cooled to room
temperature, and the solvent is removed. When the reaction was
completed, 35 g (73.8%) of the product Sub 1-5 was obtained by
using the separation method for Sub 1-1 described above.
3. Synthesis Example of Sub 1-7
##STR00041##
[0072] (1) Synthesis of Sub 1-1b
[0073] 48 g (82.4%) of the product Sub 1-1b was obtained by using
the synthesis method of Sub 1-1b described above.
(2) Synthesis of Sub 1-7
[0074] Sub 1-1b (30 g, 0.09 mol),
1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (29.7
g, 0.09 mol), Pd(PPh.sub.3).sub.4 (3.1 g, 0.003 mol), NaOH (10.8 g,
0.27 mol), THF (180 mL) and water (60 mL) were added, and the
reaction was carried out at 70.degree. C. for 6 hours. When the
reaction was completed, 35 g (85.2%) of the product Sub 1-7 was
obtained by using the separation method for Sub 1-1 described
above.
4. Synthesis Example of Sub 1-9
##STR00042##
[0075] (1) Synthesis of Sub 1-9b
[0076] naphthalen-2-ylboronic acid (23.4 g, 0.14 mol),
Pd(PPh.sub.3).sub.4 (4.8 g, 0.004 mol), NaOH (16.4 g, 0.41 mol),
THF (280 mL) and water (90 mL) were added to Sub 1-5a (40 g, 0.14
mol), and the reaction was conducted at 70.degree. C. for 6 hours.
When the reaction was completed, 38 g (81.8%) of the product Sub
1-9b was obtained by using the separation method of Sub 1-1b
described above.
(2) Synthesis of Sub 1-9
[0077] Sub 1-9b (38 g, 0.11 mol),
1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (37 g,
0.11 mol), Pd(PPh.sub.3).sub.4 (3.9 g, 0.003 mol), NaOH (13.5 g,
0.34 mol), THF (230 mL) and water (70 mL) were added, and the
reaction was carried out at 70.degree. C. for 6 hours. When the
reaction was completed, 42 g (81.1%) of the product Sub 1-9 was
obtained by using the separation method for Sub 1-1 described
above.
[0078] Meanwhile, the compound belonging to Sub 1 may be the
following compounds, but is not limited thereto, and Table 1 below
shows FD-MS (Field Desorption-Mass Spectrometry) values of the
compounds belonging to Sub 1-1.
##STR00043## ##STR00044## ##STR00045## ##STR00046##
##STR00047##
TABLE-US-00002 TABLE 1 compound FD-MS Sub 1-1 m/z =
456.23(C.sub.32H.sub.29BO.sub.2 = 456.39) Sub 1-2 m/z =
463.27(C.sub.32H.sub.22D.sub.7BO.sub.2 = 463.43) Sub 1-3 m/z =
462.26(C.sub.32H.sub.23D.sub.6BO.sub.2 = 462.43) Sub 1-4 m/z =
460.25(C.sub.32H.sub.25D.sub.4BO.sub.2 = 460.42) Sub 1-5 m/z =
469.31(C.sub.32H.sub.16D.sub.13BO.sub.2 = 469.47) Sub 1-6 m/z =
458.24(C.sub.32H.sub.27D.sub.2BO.sub.2 = 458.4) Sub 1-7 m/z =
456.23(C.sub.32H.sub.29BO.sub.2 = 456.39) Sub 1-8 m/z =
467.3(C.sub.32H.sub.18D.sub.11BO.sub.2 = 467.46) Sub 1-9 m/z =
462.26(C.sub.32H.sub.23D.sub.6BO.sub.2 = 462.43) Sub 1-10 m/z =
458.24(C.sub.32H.sub.27D.sub.2BO.sub.2 = 458.4) Sub 1-11 m/z =
463.27(C.sub.32H.sub.22D.sub.7BO.sub.2 = 463.43)
[0079] Meanwhile, the compound belonging to Sub 2 may be a compound
as follows, but is not limited thereto, and Table 2 below shows
Field Desorption-Mass Spectrometry (FD-MS) values of the compound
belonging to Sub 2.
##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052##
##STR00053## ##STR00054## ##STR00055## ##STR00056##
##STR00057##
TABLE-US-00003 TABLE 2 compound FD-MS Sub2-1 m/z =
267.06(C.sub.15H.sub.10ClN.sub.3 = 267.72) Sub2-2 m/z =
317.07(C.sub.19H.sub.12ClN.sub.3 = 317.78) Sub2-3 m/z =
317.07(C.sub.19H.sub.12ClN.sub.3 = 317.78) Sub2-4 m/z =
343.09(C.sub.21H.sub.14ClN.sub.3 = 343.81) Sub2-5 m/z =
343.09(C.sub.21H.sub.14ClN.sub.3 = 343.81) Sub2-6 m/z =
343.09(C.sub.21H.sub.14ClN.sub.3 = 343.81) Sub2-7 m/z =
393.1(C.sub.25H.sub.16ClN.sub.3 = 393.87) Sub2-8 m/z =
393.1(C.sub.25H.sub.16ClN.sub.3 = 393.87) Sub2-9 m/z =
393.1(C.sub.25H.sub.16ClN.sub.3 = 393.87) Sub2-10 m/z =
419.12(C.sub.27H.sub.18ClN.sub.3 = 419.91) Sub2-11 m/z =
367.09(C.sub.23H.sub.14ClN.sub.3 = 367.84) Sub2-12 m/z =
367.09(C.sub.23H.sub.14ClN.sub.3 = 367.84) Sub2-13 m/z =
367.09(C.sub.23H.sub.14ClN.sub.3 = 367.84) Sub2-14 m/z =
272.09(C.sub.15H.sub.5D.sub.5ClN.sub.3 = 272.75) Sub2-15 m/z =
348.12(C.sub.21H.sub.9D.sub.5ClN.sub.3 = 348.84) Sub2-16 m/z =
270.08(C.sub.15H.sub.7D.sub.3ClN.sub.3 = 270.73) Sub2-17 m/z =
367.09(C.sub.23H.sub.14ClN.sub.3 = 367.84) Sub2-18 m/z =
367.09(C.sub.23H.sub.14ClN.sub.3 = 367.84) Sub2-19 m/z =
367.09(C.sub.23H.sub.14ClN.sub.3 = 367.84) Sub2-20 m/z =
393.1(C.sub.25H.sub.16ClN.sub.3 = 393.87) Sub2-21 m/z =
393.1(C.sub.25H.sub.16ClN.sub.3 = 393.87) Sub2-22 m/z =
393.1(C.sub.25H.sub.16ClN.sub.3 = 393.87) Sub2-23 m/z =
393.1(C.sub.25H.sub.16ClN.sub.3 = 393.87) Sub2-24 m/z =
417.1(C.sub.27H.sub.16ClN.sub.3 = 417.9) Sub2-25 m/z =
417.1(C.sub.27H.sub.16ClN.sub.3 = 417.9) Sub2-26 m/z =
443.12(C.sub.29H.sub.18ClN.sub.3 = 443.93) Sub2-27 m/z =
469.13(C.sub.31H.sub.20ClN.sub.3 = 469.97) Sub2-28 m/z =
419.12(C.sub.27H.sub.18ClN.sub.3 = 419.91) Sub2-29 m/z =
419.12(C.sub.27H.sub.18ClN.sub.3 = 419.91) Sub2-30 m/z =
419.12(C.sub.27H.sub.18ClN.sub.3 = 419.91) Sub2-31 m/z =
419.12(C.sub.27H.sub.18ClN.sub.3 = 419.91) Sub2-32 m/z =
469.13(C.sub.31H.sub.20ClN.sub.3 = 469.97) Sub2-33 m/z =
469.13(C.sub.31H.sub.20ClN.sub.3 = 469.97) Sub2-34 m/z =
469.13(C.sub.31H.sub.20ClN.sub.3 = 469.97) Sub2-35 m/z =
419.12(C.sub.27H.sub.18ClN.sub.3 = 419.91) Sub2-36 m/z =
467.12(C.sub.31H.sub.18ClN.sub.3 = 467.96) Sub2-37 m/z =
467.12(C.sub.31H.sub.18ClN.sub.3 = 467.96) Sub2-38 m/z =
322.1(C.sub.19H.sub.7D.sub.5ClN.sub.3 = 322.81) Sub2-39 m/z =
277.12(C.sub.15D.sub.10ClN.sub.3 = 277.78) Sub2-40 m/z =
443.12(C.sub.29H.sub.18ClN.sub.3 = 443.93) Sub2-41 m/z =
469.13(C.sub.31H.sub.20ClN.sub.3 = 469.97) Sub2-42 m/z =
423.14(C.sub.27H.sub.14D.sub.4ClN.sub.3 = 423.94) Sub2-43 m/z =
469.13(C.sub.31H.sub.20ClN.sub.3 = 469.97)
II. Synthesis of Final Products
1. Synthesis Example of P-1
##STR00058##
[0081] Sub 1-1 (20 g, 0.04 mol), Sub 2-1 (11.7 g, 0.04 mol),
Pd(PPh.sub.3).sub.4 (1.5 g, 0.001 mol), NaOH (5.3 g, 0.13 mol), THF
(90 mL) and water (30 mL) were added, and the reaction was
conducted at 70.degree. C. for 6 hours. When the reaction is
completed, the temperature of the reactant is cooled to room
temperature, and the reaction solvent is removed. Then, the
concentrated reactant was separated using a silica gel column or
recrystallization method to obtain 22 g (89.4%) of product P-1.
2. Synthesis Example of P-3
##STR00059##
[0083] Sub 1-1 (20 g, 0.04 mol), Sub 2-3 (13.9 g, 0.04 mol),
Pd(PPh.sub.3).sub.4 (1.5 g, 0.001 mol), NaOH (5.3 g, 0.13 mol), THF
(90 mL) and water (30 mL) were added, and the reaction was
conducted at 70.degree. C. for 6 hours. When the reaction was
completed, 23 g (85.8%) of the product P-3 was obtained by using
the separation method for P-1 described above.
3. Synthesis Example of P-10
##STR00060##
[0085] Sub 1-1 (33 g, 0.07 mol), Sub 2-28 (30.3 g, 0.07 mol),
Pd(PPh.sub.3).sub.4 (2.5 g, 0.002 mol), NaOH (8.7 g, 0.22 mol), THF
(90 mL) and water (50 mL) were added, and the reaction was
conducted at 70.degree. C. for 6 hours. When the reaction was
completed, 46 g (89.1%) of the product P-10 was obtained by using
the separation method for P-1 described above.
4. Synthesis Example of P-25
##STR00061##
[0087] Sub 1-2 (30 g, 0.06 mol), Sub 2-1 (17.3 g, 0.06 mol),
Pd(PPh.sub.3).sub.4 (2.2 g, 0.002 mol), NaOH (7.8 g, 0.19 mol), THF
(130 mL) and water (40 mL) were added, and the reaction was
conducted at 70.degree. C. for 6 hours. When the reaction was
completed, 30 g (81.5%) of the product P-25 was obtained by using
the separation method for P-1 described above.
5. Synthesis Example of P-29
##STR00062##
[0089] Sub 1-2 (35 g, 0.08 mol), Sub 2-14 (20.6 g, 0.08 mol),
Pd(PPh.sub.3).sub.4 (2.6 g, 0.002 mol), NaOH (9.1 g, 0.23 mol), THF
(150 mL) and water (50 mL) were added, and the reaction was
conducted at 70.degree. C. for 6 hours. When the reaction was
completed, 40 g (92.3%) of the product P-29 was obtained by using
the separation method for P-1 described above.
6. Synthesis Example of P-34
##STR00063##
[0091] Sub 1-7 (30 g, 0.07 mol), Sub 2-2 (20.9 g, 0.07 mol),
Pd(PPh.sub.3).sub.4 (2.3 g, 0.002 mol), NaOH (7.9 g, 0.20 mol), THF
(130 mL) and water (40 mL) were added, and the reaction was
conducted at 70.degree. C. for 6 hours. When the reaction was
completed, 32 g (79.6%) of the product P-34 was obtained by using
the separation method for P-1 described above.
7. Synthesis Example of P-51
##STR00064##
[0093] Sub 1-7 (20 g, 0.04 mol), Sub 2-12 (16.1 g, 0.04 mol),
Pd(PPh.sub.3).sub.4 (1.5 g, 0.001 mol), NaOH (5.3 g, 0.13 mol), THF
(90 mL) and water (30 mL) were added, and the reaction was
conducted at 70.degree. C. for 6 hours. When the reaction was
completed, 26 g (89.7%) of the product P-51 was obtained by using
the separation method for P-1 described above.
8. Synthesis Example of P-62
##STR00065##
[0095] Sub 1-9 (15 g, 0.03 mol), Sub 2-14 (8.8 g, 0.03 mol),
Pd(PPh.sub.3).sub.4 (1.1 g, 0.001 mol), NaOH (3.9 g, 0.10 mol), THF
(65 mL) and water (20 mL) were added, and the reaction was
conducted at 70.degree. C. for 6 hours. When the reaction was
completed, 15 g (80.8%) of the product P-62 was obtained by using
the separation method for P-1 described above.
[0096] Meanwhile, FD-MS values of compounds P-1 to P-64 of the
present invention prepared according to the above synthesis
examples are shown in Table 3 below.
TABLE-US-00004 TABLE 3 compound FD-MS P-1 m/z =
561.22(C.sub.41H.sub.27N.sub.3 = 561.69) P-2 m/z =
611.24(C.sub.45H.sub.29N.sub.3 = 611.75) P-3 m/z =
611.24(C.sub.45H.sub.29N.sub.3 = 611.75) P-4 m/z =
661.25(C.sub.49H.sub.31N.sub.3 = 661.81) P-5 m/z =
661.25(C.sub.49H.sub.31N.sub.3 = 661.81) P-6 m/z =
637.25(C.sub.47H.sub.31N.sub.3 = 637.79) P-7 m/z =
637.25(C.sub.47H.sub.31N.sub.3 = 637.79) P-8 m/z =
637.25(C.sub.47H.sub.31N.sub.3 = 637.79) P-9 m/z =
687.27(C.sub.51H.sub.33N.sub.3 = 687.85) P-10 m/z =
713.28(C.sub.53H.sub.35N.sub.3 = 713.88) P-11 m/z =
713.28(C.sub.53H.sub.35N.sub.3 = 713.88) P-12 m/z =
713.28(C.sub.53H.sub.35N.sub.3 = 713.88) P-13 m/z =
713.28(C.sub.53H.sub.35N.sub.3 = 713.88) P-14 m/z =
687.27(C.sub.51H.sub.33N.sub.3 = 687.85) P-15 m/z =
687.27(C.sub.51H.sub.33N.sub.3 = 687.85) P-16 m/z =
763.3(C.sub.57H.sub.37N.sub.3 = 763.94) P-17 m/z =
661.25(C.sub.49H.sub.31N.sub.3 = 661.81) P-18 m/z =
661.25(C.sub.49H.sub.31N.sub.3 = 661.81) P-19 m/z =
711.27(C.sub.53H.sub.33N.sub.3 = 711.87) P-20 m/z =
763.3(C.sub.57H.sub.37N.sub.3 = 763.94) P-21 m/z =
661.25(C.sub.49H.sub.31N.sub.3 = 661.81) P-22 m/z =
687.27(C.sub.51H.sub.33N.sub.3 = 687.85) P-23 m/z =
761.28(C.sub.57H.sub.35N.sub.3 = 761.93) P-24 m/z =
763.3(C.sub.57H.sub.37N.sub.3 = 763.94) P-25 m/z =
568.26(C.sub.41H.sub.20D.sub.7N.sub.3 = 568.73) P-26 m/z =
567.26(C.sub.41H.sub.21D.sub.6N.sub.3 = 567.72) P-27 m/z =
616.27(C.sub.45H.sub.24D.sub.5N.sub.3 = 616.78) P-28 m/z =
641.28(C.sub.47H.sub.27D.sub.4N.sub.3 = 641.81) P-29 m/z =
573.3(C.sub.41H.sub.15D.sub.12N.sub.3 = 573.76) P-30 m/z =
624.32(C.sub.45H.sub.16D.sub.13N.sub.3 = 624.83) P-31 m/z =
573.3(C.sub.41H.sub.15D.sub.12N.sub.3 = 573.76) P-32 m/z =
646.31(C.sub.47H.sub.22D.sub.9N.sub.3 = 646.84) P-33 m/z =
561.22(C.sub.41H.sub.27N.sub.3 = 561.69) P-34 m/z =
611.24(C.sub.45H.sub.29N.sub.3 = 611.75) P-35 m/z =
611.24(C.sub.45H.sub.29N.sub.3 = 611.75) P-36 m/z =
661.25(C.sub.49H.sub.31N.sub.3 = 661.81) P-37 m/z =
661.25(C.sub.49H.sub.31N.sub.3 = 661.81) P-38 m/z =
661.25(C.sub.49H.sub.31N.sub.3 = 661.81) P-39 m/z =
687.27(C.sub.51H.sub.33N.sub.3 = 687.85) P-40 m/z =
711.27(C.sub.53H.sub.33N.sub.3 = 711.87) P-41 m/z =
687.27(C.sub.51H.sub.33N.sub.3 = 687.85) P-42 m/z =
737.28(C.sub.55H.sub.35N.sub.3 = 737.91) P-43 m/z =
763.3(C.sub.57H.sub.37N.sub.3 = 763.94) P-44 m/z =
713.28(C.sub.53H.sub.35N.sub.3 = 713.88) P-45 m/z =
713.28(C.sub.53H.sub.35N.sub.3 = 713.88) P-46 m/z =
713.28(C.sub.53H.sub.35N.sub.3 = 713.88) P-47 m/z =
763.3(C.sub.57H.sub.37N.sub.3 = 763.94) P-48 m/z =
713.28(C.sub.53H.sub.35N.sub.3 = 713.88) P-49 m/z =
687.27(C.sub.51H.sub.33N.sub.3 = 687.85) P-50 m/z =
687.27(C.sub.51H.sub.33N.sub.3 = 687.85) P-51 m/z =
661.25(C.sub.49H.sub.31N.sub.3 = 661.81) P-52 m/z =
737.28(C.sub.55H.sub.35N.sub.3 = 737.91) P-53 m/z =
761.28(C.sub.57H.sub.35N.sub.3 = 761.93) P-54 m/z =
687.27(C.sub.51H.sub.33N.sub.3 = 687.85) P-55 m/z =
661.25(C.sub.49H.sub.31N.sub.3 = 661.81) P-56 m/z =
763.3(C.sub.57H.sub.37N.sub.3 = 763.94) P-57 m/z =
564.24(C.sub.41H.sub.24D.sub.3N.sub.3 = 564.71) P-58 m/z =
618.28(C.sub.45H.sub.22D.sub.7N.sub.3 = 618.79) P-59 m/z =
717.31(C.sub.53H.sub.31D.sub.4N.sub.3 = 717.91) P-60 m/z =
573.3(C.sub.41H.sub.15D.sub.12N.sub.3 = 573.76) P-61 m/z =
672.32(C.sub.49H.sub.20D.sub.11N.sub.3 = 672.88) P-62 m/z =
572.29(C.sub.41H.sub.16D.sub.11N.sub.3 = 572.76) P-63 m/z =
568.26(C.sub.41H.sub.20D.sub.7N.sub.3 = 568.73) P-64 m/z =
577.32(C.sub.41H.sub.11D.sub.16N.sub.3 = 577.79)
[0097] Reorganization energy (hereinafter, abbreviated as RE)
refers to energy lost due to a change in molecular structure
arrangement when electric charges (electrons, holes) move. It
depends on molecular geometry, and has a characteristic that the
value decreases as the difference between the potential energy
surface (hereinafter, abbreviated as PES) in the neutral state and
the PES in the charge state decreases. The RE value can be obtained
by the following formula.
RE.sub.hole:.lamda..sup.+=(E.sub.NOCE-E.sub.COCE)+(E.sub.CONE-E.sub.NONE-
)
RE.sub.elec:.lamda..sup.-=(E.sub.NOAE-E.sub.AOAE)+(E.sub.AONE-E.sub.NONE-
)
[0098] Each factor can be defined as follows. [0099] NONE: Neutral
geometry of neutral molecules (hereinafter, NO opt.) [0100] NOAE:
Anion geometry of a neutral molecule [0101] NOCE: Cation geometry
of a neutral molecule [0102] AONE: Neutral geometry of anion
molecule [0103] AOAE: Anion geometry of anion molecule
(hereinafter, AO opt.) [0104] CONE: Neutral geometry of cation
molecule [0105] COCE: Cation geometry of cation molecule
(hereinafter, CO opt.)
[0106] Reorganization energy and mobility are in inverse proportion
to each other, and under the condition that they have the same r
and T values, the RE value directly affects mobility for each
material. The relation between RE value and mobility is expressed
as follows.
.mu. = k .times. r 2 2 .times. k B .times. T / e ##EQU00001## k = (
4 .times. .pi. 2 h ) .times. t 2 4 .times. .pi..lamda. .times.
.times. k B .times. T .times. exp .function. [ - .lamda. 4 .times.
k B .times. T ] ##EQU00001.2##
[0107] Each factor can be defined as follows. [0108] .lamda.:
Reorganization energy [0109] .mu.: mobility [0110] r: dimer
displacement [0111] t: intermolecular charge transfer matrix
element
[0112] From the above formula, it can be seen that the lower the RE
value, the faster the mobility.
[0113] The RE value requires a simulation tool that can calculate
the potential energy according to the molecular structure, and we
used Gaussian09 (hereafter, G09) and the Jaguar (hereafter, JG)
module of Schrodinger Materials Science. Both G09 and JG are tools
to analyze the properties of molecules through quantum mechanical
(hereafter, QM) calculations, and have the function of optimizing
the molecular structure or calculating the energy for a given
molecular structure (single-point energy).
[0114] The process of calculating QM in molecular structure
requires large computational resources, and we use two cluster
servers for these calculations. Each cluster server consists of 4
node workstations and 1 master workstation, and each node performed
molecular QM calculations by parallel computing through symmetric
multi-processing (SMP) using a central processing unit (CPU) of 36
or more cores.
[0115] Using G09, calculate the optimized molecular structure and
its potential energy (NONE/COCE) in the neutral/charged state
required for rearrangement energy. The charge state potential
energy (NOCE) of the structure optimized for the neutral state and
the neutral state potential energy (CONE) of the structure
optimized for the charge state were calculated by changing only the
charges to the two optimized structures. Then, the rearrangement
energy was calculated according to the following relation.
RE.sub.charge:.lamda.=(E.sub.NOCE-E.sub.COCE)+(E.sub.CONE-E.sub.NONE)
[0116] Because Schrodinger provides a function to automatically
perform such a calculation process, the potential energy according
to each state was sequentially calculated through the JG module by
providing the molecular structure (NO) of the basic state, and the
RE value was calculated.
[0117] Meanwhile, the RE values of the present invention calculated
according to the above calculation method are shown in Table 4
below.
TABLE-US-00005 TABLE 4 compound Reorganization energy (RE) P-1
0.157 P-3 0.158 P-25 0.156 P-26 0.157
[0118] Otherwise, the RE values of the comparative compounds
calculated according to the calculation method as described above
are shown in Table 5 below.
TABLE-US-00006 TABLE 5 compound Reorganization energy (RE)
comparative compound A 0.299 comparative compound B 0.195
comparative compound C 0.191 comparative compound D 0.261
[Example 1] Red Organic Light Emitting Device (Phosphorescent
Host)
[0119] An organic electroluminescent device was manufactured
according to a conventional method by using the compound obtained
through synthesis as a light emitting host material of the emitting
layer. First, a N1-(naphthalen-2-yl)-N4,
N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diami-
ne (abbreviated as 2-TNATA) film was vacuum-deposited on the ITO
layer (anode) formed on a glass substrate to form a 60 nm-thick
hole injection layer, and
4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter
abbreviated as -NPD) as a hole transport compound on the hole
injection layer was vacuum-deposited to a thickness of 60 nm to
form a hole transport layer.
[0120] As a host on the hole transport layer, the compound (P-1) of
the present invention represented by Formula (1) was used, and
(piq).sub.2Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate]
as a dopant material was doped at a weight ratio of 95:5 to deposit
an emitting layer to a thickness of 30 nm). Subsequently,
(1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum
(abbreviated as BAlq) as a hole-blocking layer was vacuum-deposited
to a thickness of 10 nm, and as an electron transport layer,
tris(8-quinolinol)aluminum (abbreviated as Alq3) was deposited to a
thickness of 40 nm. Then, as an electron injection layer, LiF, an
alkali metal halide, was deposited to a thickness of 0.2 nm, and
then, Al was deposited to a thickness of 150 nm and used as a
cathode to prepare an organic electroluminescent device.
[Example 2] to [Example 4]
[0121] An organic electroluminescent device was prepared in the
same manner as in Example 1, except that the compound of the
present invention shown in Table 6 was used instead of the compound
(P-1) of the present invention as the host material of the emitting
layer.
Example 5
[0122] An organic electroluminescent device was manufactured in the
same manner as in Example 1, except that the compound (P-1) of the
present invention and the following compound DSNL1 were used as a
host material for the emitting layer in a weight ratio of 5:5.
[Example 6] to [Example 24]
[0123] An organic electroluminescent device was prepared in the
same manner as in Example 1, except that the compounds of the
present invention shown in Table 6 and the following compound DSNL1
or DSNL2 were used in a weight ratio of 5:5 instead of the compound
(P-1) of the present invention as the first compound as the host
material of the emitting layer.
##STR00066##
[Comparative Example 1] to [Comparative Example 4]
[0124] An organic electroluminescent device was manufactured in the
same manner as in Example 1, except that the following Comparative
Compounds A to D were used as host materials for the emitting
layer.
##STR00067##
[Comparative Example 5] to [Comparative Example 12]
[0125] An organic electroluminescent device was manufactured in the
same manner as in Example 1, except that the comparative compound A
to the comparative compound D and the compound DSNL1 or DSNL2 were
used in a weight ratio of 5:5 as host materials for the emitting
layer.
[0126] By applying a forward bias DC voltage to the organic
electronic devices prepared in Examples 1 to 24 and Comparative
Examples 1 to 12 prepared in this way, Electroluminescence (EL)
characteristics were measured with PR-650 from photo research, and
as a result of the measurement, the T95 lifetime was measured using
a lifetime measuring device manufactured by McScience at 2500
cd/m.sup.2 standard luminance. Table 6 below shows the device
fabrication and evaluation results.
TABLE-US-00007 TABLE 6 Current first second Voltage Density
Brightness Efficiency compound compound (v) (mA/cm.sup.2)
(cd/m.sup.2) (cd/A) T (95) comparative comparative -- 6.1 18.9 2500
13.2 85.9 example (1) compound A comparative comparative -- 6.4
18.2 2500 13.7 86.5 example (2) compound B comparative comparative
-- 6.8 16.9 2500 14.8 78.6 example (3) compound C comparative
comparative -- 5.8 21.7 2500 11.5 55.7 example (4) compound D
comparative DSNL1 comparative 5.3 13.4 2500 18.7 106.4 example (5)
compound A comparative comparative 5.4 12.2 2500 20.5 106.8 example
(6) compound B comparative comparative 5.6 11.7 2500 21.4 103.2
example (7) compound C comparative comparative 5.1 16.4 2500 15.2
101.2 example (8) compound D comparative DSNL2 comparative 5.2 13.7
2500 18.2 104.2 example (9) compound A comparative comparative 5.3
12.7 2500 19.7 106.8 example (10) compound B comparative
comparative 5.5 11.8 2500 21.2 102.5 example (11) compound C
comparative comparative 5.0 14.9 2500 16.8 99.9 example (12)
compound D example (1) P-1 -- 5.0 10.4 2500 24.1 116.8 example (2)
P-7 -- 5.1 10.8 2500 23.2 113.5 example (3) P-25 -- 5.0 10.7 2500
23.4 117.1 example (4) P-43 -- 5.3 11.3 2500 22.1 109.8 example (5)
DSNL1 P-1 4.6 7.5 2500 33.2 142.2 example (6) P-3 4.6 8.2 2500 30.5
133.0 example (7) P-7 4.7 8.0 2500 31.1 138.5 example (8) P-17 4.5
8.5 2500 29.4 132.7 example (9) P-25 4.6 7.6 2500 32.8 144.7
example (10) P-34 4.8 9.9 2500 25.3 136.7 example (11) P-43 4.9 9.2
2500 27.1 131.4 example (12) P-47 4.9 9.5 2500 26.4 129.8 example
(13) P-53 4.7 10.0 2500 25.1 128.9 example (14) P-60 4.8 9.0 2500
27.7 141.8 example (15) DSNL2 P-1 4.5 7.6 2500 32.8 133.8 example
(16) P-3 4.4 8.3 2500 30.0 121.5 example (17) P-7 4.6 8.2 2500 30.5
127.1 example (18) P-17 4.3 8.6 2500 29.0 121.7 example (19) P-25
4.5 7.7 2500 32.4 135.6 example (20) P-34 4.7 10.0 2500 25.1 125.3
example (21) P-43 4.9 9.4 2500 26.7 120.0 example (22) P-47 4.8 9.5
2500 26.2 119.4 example (23) P-53 4.6 10.4 2500 24.1 119.1 example
(24) P-60 4.7 9.2 2500 27.3 129.5
[0127] As can be seen from the results in Table 6, when the
compound of the present invention is used as a material for the
emitting layer, it can be seen that the driving voltage is lowered
and the efficiency and lifespan are significantly improved compared
to the case of using the comparative compounds A to D.
[0128] It was found that the overall device results were improved
when different types of compounds were used through mixing than
when the emitting layer compound was used alone. This showed the
same trend in the results of Comparative Compounds A to D and in
the device results of the present invention.
[0129] More specifically, the compound of the present invention has
a lower RE value than the comparative compound. It can be seen that
the compound of the present invention has a lower RE value only
when a plurality of naphthyl groups linked to a phenylene group are
bonded to a triazine and their bonding positions are specific
positions described in the present invention. Moreover, when a
substituent having an excessive number of carbon atoms in the
substituted configuration is substituted, it is applied as a factor
to increase the RE value.
[0130] Since a low RE value is in inverse proportion to mobility, a
low RE value means high mobility, and this mobility means a fast
EOD. Overall, it can be seen that the compound of the present
invention having a fast EOD value has the characteristics of a fast
driving voltage, high efficiency, and long lifespan.
[0131] Looking at the compounds of the present invention, it can be
seen that the RE value has a value in the range of 0.155 to 0.170,
and as a common characteristic of these compounds, the driving
voltage is pulled and the efficiency is increased.
[0132] When the emitting layer was composed of a plurality of
mixtures, the characteristics were different depending on the type
of the first compound and the second compound, the device results
of the compound of the present invention and the comparative
compound showed the same tendency. Finally, it can be seen that the
driving, efficiency, and lifespan are determined according to the
injection characteristics of holes and electrons into the dopant.
In the present invention, it can be seen that through the
relationship between the RE value and mobility, the overall driving
reduction effect, efficiency and lifetime increase effect are
brought. Moreover, the present invention is an invention for a
compound in which three substituents are introduced into triazine,
and when a specific substituent is combined, it has a positive
effect on overall mobility and acts as a ratio of a hole to an
electron (for example, energy balance, stability, etc.), showing an
overall improved result.
[0133] Comparing the example compounds, the RE value is determined
according to the type of substituent substituted in the same
skeleton, the injection and migration characteristics of holes and
electrons vary according to different RE values. Therefore,
according to the type of the substituent, the compounds of the
examples show different properties from each other.
[0134] Although exemplary embodiments of the present invention have
been described for illustrative purposes, those skilled in the art
will appreciate that various modifications, additions and
substitutions are possible, without departing from the scope and
spirit of the invention as disclosed in the accompanying claims.
Therefore, the embodiment disclosed in the present invention is
intended to illustrate the scope of the technical idea of the
present invention, and the scope of the present invention is not
limited by the embodiment. The scope of the present invention shall
be construed on the basis of the accompanying claims, and it shall
be construed that all of the technical ideas included within the
scope equivalent to the claims belong to the present invention.
* * * * *