KR101247626B1 - Compounds for organic photoelectric device and organic photoelectric device containing the same - Google Patents

Abstract

The present invention relates to a compound for an organic photoelectric device and an organic photoelectric device including the same, wherein the compound for an organic photoelectric device includes a compound represented by the following Chemical Formula 1.

[Formula 1]

Definitions of A ₁ , A ₂ , R _a to R _e , and n in Chemical Formula 1 are as described in the specification.

The compound for an organic photoelectric device according to the present invention may play a role of hole injection, hole transport, light emission, or electron injection and / or electron transport in an organic photoelectric device including an organic light emitting device by using phosphorescent light emission, and an appropriate dopant In addition, it can also serve as a light emitting host. In addition, the compound is very excellent in electrochemical stability and thermal stability, it is possible to manufacture an organic photoelectric device having an excellent effect in terms of efficiency, driving voltage and life by applying to the organic photoelectric device.

Organic, light emitting, phosphorescent, hole transport, efficiency, organic photoelectric device

Description

COMPOUNDS FOR ORGANIC PHOTOELECTRIC DEVICE AND ORGANIC PHOTOELECTRIC DEVICE CONTAINING THE SAME

The present invention relates to a compound for an organic photoelectric device and an organic photoelectric device including the same. More particularly, the present invention provides a hole in an organic photoelectric device including an organic light emitting device by using phosphorescent light emission and having excellent electrochemical stability and thermal stability. Compounds for organic photoelectric devices that can act as light emitting hosts with the role of injection, hole transport, luminescence, or electron injection and / or electron transport, and with suitable dopants, including the compounds to improve efficiency, drive voltage, and lifetime. It relates to an organic photoelectric device that can be improved.

A photoelectric device is a device that converts light energy into electrical energy or vice versa in a broad sense. Examples of such photoelectric devices are organic electroluminescent devices, solar cells, and transistors. Etc. Among such optoelectronic devices, organic light emitting diodes (OLEDs), in particular, are drawing attention as the demand for flat panel displays increases.

The organic electroluminescent device converts electrical energy into light by applying an electric current to an organic light emitting material, and includes an anode made of a transparent electrode, an organic thin film including a light emitting region, and a cathode made of a metal electrode. It has a structure formed on a glass substrate. In this case, the organic thin film may include a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer or an electron injection layer, and may further include an electron blocking layer or a hole blocking layer due to light emission characteristics of the light emitting layer.

When an electric field is applied to the organic electroluminescent device having such a structure, holes and electrons are injected from the anode and the cathode, respectively, and the injected holes and electrons are recombined in the light emitting layer through the respective hole transport layer and the electron transport layer, thereby emitting light. ). The light-excited excitons thus formed emit light while transitioning to ground states. Light emission is divided into fluorescence using singlet excitons and phosphorescence using triplet states according to its mechanism.

In 1987, Eastman Kodak Co., Ltd. developed for the first time an organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987], and in 1987, CW Tang et al. Reported a device having practical performance for an organic electroluminescent device (Applied Physics Letters, Vol. 51, No. 12, 913-915 (1987)). This document describes a structure in which a thin film (hole transport layer) of a diamine derivative and a thin film (electron transport light emitting layer) of Alq _{3 (} tris (8-hydroxy quinolate) aluminum) are laminated as an organic layer.

Recently, it has been known that phosphorescent as well as fluorescent light emitting materials can be used as light emitting materials of organic electroluminescent devices (DFO'Brien et al., Applied Physics Letters, 74 (3), 442-444, 1999; MA Baldo Et al., Applied Physics letters, 75 (1), 4-6, 1999). These phosphorescent luminescences are characterized by the transfer of electrons from the ground state to the excited state, followed by intersystem crossing, After the non-luminescent transition, the triplet excitons consist of a mechanism that emits light while transitioning to the ground state. At this time, the half-life (luminescence time, lifetime) is greater than that of fluorescence because the triplet excitons cannot directly transition to the ground state (spin forbidden), and thus undergo the process of transition to the ground state after the flipping of the electron spin. Has a characteristic of lengthening. That is, the emission duration of fluorescence emission is only several nanoseconds, but the phosphorescence emission corresponds to several micro seconds, which is a relatively long time.

In addition, in quantum mechanical terms, when the holes injected from the anode and the electrons injected from the cathode recombine to form a light-emitting excitons in the organic electroluminescent device, the generation ratio of the singlet and triplet is 1: 3 in the organic EL device. Triplet luminescence excitons are generated about three times more than singlet luminescence excitons. Therefore, in the case of fluorescence, the probability of singlet excited state is 25% (triple state 75%) and there is a limit of luminous efficiency, whereas phosphorescence can be used to triplet 75% and singlet excited state 25%. The internal quantum efficiency is up to 100%. Therefore, in the case of using the phosphorescent material, there is an advantage that can achieve a light emission efficiency about four times higher than the fluorescent material.

In the organic electroluminescent device having the structure as described above, in order to increase the efficiency and stability of the light emitting state, a light emitting pigment (dopant) may be added to the light emitting layer (host). In such a structure, the efficiency and performance of the light emitting device varies depending on which host material is used for the light emitting layer, and naphthalene, anthracene, phenanthrene, tetracene, pyrene, benzopyrene, chrysene, pisene, Carbazole, fluorene, biphenyl, terphenyl, triphenylene oxide, dihalobiphenyl, trans-stilbene and 1,4-diphenylbutadiene are shown as examples of organic host materials. Has been.

In addition, 4,4-N, N-dicarbazolebiphenyl (CBP) was mainly used as a host material, which has a glass transition temperature (T _g ) of 110 ° C. or lower and a thermal decomposition temperature (T _d ) of 400 ° C. Since the thermal stability is low and the symmetry is too good below, it is easy to crystallize, and as a result of the heat resistance test of an element, the short circuit and the pixel defect were discovered. In addition, most host materials, including CBP, are materials having better hole transportability than electron transport properties, and thus the luminous efficiency of the device is reduced as excitons are not effectively formed in the light emitting layer because the movement of injected holes is faster than that of injected electrons. Appeared.

Therefore, in order to implement a highly efficient long-life phosphorescent organic photoelectric device, it is necessary to develop a phosphorescent host material having high electrical and thermal stability and having bipolar characteristics capable of transferring both holes and electrons well.

One embodiment of the present invention is excellent in terms of electrochemical stability and thermal stability, to perform the role of hole injection, hole transport, light emission, or electron injection and / or electron transport, and as a light emitting host with a suitable dopant It is to provide a suitable compound for an organic photoelectric device.

Another embodiment of the present invention is to provide an organic photoelectric device having excellent efficiency and driving voltage characteristics, including the compound for an organic photoelectric device.

The technical problems to be achieved by the present invention are not limited to the technical problems mentioned above, and other technical problems not mentioned will be clearly understood by the average person from the following description.

According to one embodiment of the present invention, a compound for an organic photoelectric device represented by Formula 1 is provided:

[Formula 1]

In Formula 1,

A ₁ is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 hetero arylene group; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; NR, wherein R is hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; a group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms Is selected from the group consisting of),

A ₂ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 heteroaryl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; NR'R ", wherein R 'and R" are each independently hydrogen, substituted or unsubstituted aryl group having 6 to 30 carbon atoms; substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; substituted or unsubstituted Selected from the group consisting of alkyl groups having 1 to 30 carbon atoms.

R _a to R _e are the same as or different from each other, and each independently represent a substituted or unsubstituted lower alkyl group having 1 to 10 carbon atoms, carbazolyl group or arylamine group having 6 to 20 carbon atoms,

Provided that at least one selected from A ₁ and A ₂ includes an aromatic ring,

n is an integer of 0 to 3, provided that when n is an integer of 2 or more, two or more A ₁ may be the same or different from each other.

According to another embodiment of the present invention, an anode, a cathode, and an organic thin film layer interposed between the anode and the cathode, the organic thin film layer provides an organic photoelectric device comprising the compound for the organic photoelectric device.

Other specific details of embodiments of the present invention are included in the following detailed description.

The compound for an organic photoelectric device according to the embodiment of the present invention has a glass transition temperature (T _g ) of 120 ° C. or more and a thermal decomposition temperature (T _d ) of 400 ° C. or more, and has a host material having excellent thermal stability and electrochemical stability. Since it can be used as a hole transport material, or an electron transport material, it can be very usefully applied to the organic thin film layer of the organic photoelectric device.

Another embodiment of the present invention provides an organic photoelectric device having a high luminous efficiency and low lifespan even at a low driving voltage, including the compound for an organic photoelectric device.

Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

As used herein, unless otherwise defined, "substituted" means an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a fluorine group, and a cya Mean substituted with a substituent selected from the group consisting of no group.

Unless otherwise defined herein, "hetero" includes one to three heteroatoms selected from the group consisting of N, O, S, and P in one ring group, and the rest is preferably carbon. .

According to one embodiment of the present invention, a compound for an organic photoelectric device represented by Formula 1 is provided:

[Formula 1]

In Formula 1,

A ₁ is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 hetero arylene group; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; NR, wherein R is hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; a group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms Is selected from the group consisting of),

A ₂ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 heteroaryl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; NR'R ", wherein R 'and R" are each independently hydrogen, substituted or unsubstituted aryl group having 6 to 30 carbon atoms; substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; substituted or unsubstituted Selected from the group consisting of alkyl groups having 1 to 30 carbon atoms.

R _a to R _e are the same as or different from each other, and each independently represent a substituted or unsubstituted lower alkyl group having 1 to 10 carbon atoms, carbazolyl group or arylamine group having 6 to 20 carbon atoms,

However, at least one selected from A ₁ and A ₂ includes an aromatic ring.

In addition, n is an integer of 0 to 3, provided that when n is an integer of 2 or more, two or more A ₁ may be the same as or different from each other.

The carbazole group in the formula (1) functions as a hole transport group, spirofluorene (spirofluorene) performs a function to improve the thermal stability and electrochemical stability,-[A ₁ ] _n -A ₂ increases the molecular weight material itself Since the glass transition temperature (T _g ) is 120 ℃ or more, the thermal decomposition temperature (T _d ) is 400 ℃ or more, so as to improve the stability of the host material, hole transport material, having excellent thermal stability and electrochemical stability, Or it can be used as an electron transfer material, it can be very usefully applied to organic thin film layers, such as organic light emitting layer, charge transport layer of an organic photoelectric device.

In Formula 1, A ₁ is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and A ₂ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or NR'R ", wherein R 'and R" are each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; substituted or unsubstituted In the case of selected from the group consisting of an alkyl group having 1 to 30 ring carbon atoms, it is possible to obtain a better compound in terms of thermal stability and electrochemical stability.

Compound for an organic photoelectric device according to another embodiment of the present invention may be represented by the following formula (2):

[Formula 2]

In Chemical Formula 2

A ₁ is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 hetero arylene group; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; NR, wherein R is hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; a group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms Is selected from the group consisting of),

X is N or P,

R ₁ and R ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 heteroaryl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; NR'R ", wherein R 'and R" are each independently hydrogen, substituted or unsubstituted aryl group having 6 to 30 carbon atoms; substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; substituted or unsubstituted Selected from the group consisting of alkyl groups having 1 to 30 carbon atoms.), Wherein R ₁ and R ₂ may form a fusion ring.

R _a to R _e are the same as or different from each other, and each independently represent a substituted or unsubstituted lower alkyl group having 1 to 10 carbon atoms, carbazolyl group or arylamine group having 6 to 20 carbon atoms,

Provided that at least one selected from A ₁ , R _1, and R ₂ includes an aromatic ring.

In addition, n is an integer of 1 to 3, provided that when n is an integer of 2 or more, two or more A ₁ may be the same or different from each other.

In addition, the compound for an organic photoelectric device according to another embodiment of the present invention may be represented by the following formula (3):

(3)

In Chemical Formula 3

A ₁ , A ₃ and A ₄ are the same as or different from each other, and each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 hetero arylene group; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; NR, wherein R is hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; a group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms Is selected from the group consisting of),

X, Y and Z are N or P,

R ₃ to R ₆ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; NR'R ", wherein R 'and R" are each independently hydrogen, substituted or unsubstituted aryl group having 6 to 30 carbon atoms; substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; substituted or unsubstituted Selected from the group consisting of alkyl groups having 1 to 30 carbon atoms.), Wherein R ₃ to R ₆ may form a fusion ring.

R _a to R _e are the same as or different from each other, and each independently represent a substituted or unsubstituted lower alkyl group having 1 to 10 carbon atoms, carbazolyl group or arylamine group having 6 to 20 carbon atoms,

However, at least one selected from A ₁ , A ₃ , A _4, and R ₃ to R ₆ includes an aromatic ring.

In addition, n is an integer of 1 to 3, provided that when n is an integer of 2 or more, two or more A ₁ may be the same or different from each other.

In the case where each terminal group represented by R ₁ , R ₂ , and R ₃ to R ₆ of Formulas 2 and 3 is a heteroaryl group such as pyridine, electron injection characteristics are excellent, and therefore, more preferable.

In addition, the terminal groups represented by R ₁ , R ₂ , and R ₃ to R ₆ of Formulas 2 and 3 may independently form a fusion ring. As a more preferable example when the fusion ring is formed, there may be mentioned a compound for an organic photoelectric device represented by the following general formula (4):

[Formula 4]

In Chemical Formula 4

A ₁ is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 hetero arylene group; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; NR, wherein R is hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; a group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms Is selected from the group consisting of),

R _a to R _j are the same as or different from each other, and each independently represent a substituted or unsubstituted lower alkyl group having 1 to 10 carbon atoms, carbazolyl group or arylamine group having 6 to 20 carbon atoms,

n is an integer of 1 to 3, provided that when n is an integer of 2 or more, two or more A ₁ may be the same or different from each other.

Compound for an organic photoelectric device according to an embodiment of the present invention may be a compound represented by the following formula (5) or a mixture thereof. However, the present invention is not limited to the compound represented by the following Formula 5:

[Chemical Formula 5]

The compound for an organic photoelectric device according to the embodiment of the present invention has a glass transition temperature (T _g ) of 120 ° C. or more, a thermal decomposition temperature (T _d ) of 400 ° C. or more, and more preferably, a glass transition temperature (T _g ). Is in the range of 120 to 200 ° C, and the thermal decomposition temperature (T _d ) is in the range of 400 to 600 ° C. Thus, it can be used as a host material or charge transport material having thermal stability and electrochemical stability. More preferably, the pyrolysis temperature T _d may be 430 ° C. or more.

The compound for an organic photoelectric device according to the embodiment of the present invention may be used in an organic thin film layer to improve efficiency characteristics of the organic photoelectric device and to lower driving voltage. In addition, the life characteristics can be improved.

In particular, the compound for an organic photoelectric device may be used alone, but may be used as a host material that may be combined with a dopant. A dopant is a guest or dopant because it is a compound having a high luminous ability and used in a small amount in a host. That is, the dopant is a material that emits light by doping the host material, and generally a material such as a metal complex that emits light by multiplet excitaion that excites above a triplet state is used. .

Such dopants may be any of red (R), green (G), blue (B) or white (W) fluorescent or phosphorescent dopant materials generally used in the art, but in particular, dopants using phosphorescent dopant materials may be used. It is preferable. Basically, it is more preferable that the luminescence quantum efficiency is high, does not aggregate well, and is uniformly distributed in the host material.

The organic thin film layer preferably contains a phosphorescent compound as a dopant. As the phosphorescent compound, a metal complex or the like that emits light by multiplet excitation to be excited in a triplet state or more is preferable. Preferred examples of the phosphorescent dopant are organometallic compounds containing an element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, and combinations thereof. As a more specific example, red phosphorescent dopants include PtOEP, Ir (Piq) ₂ (acac) (Piq = 1-phenylisoquinoline, acac = pentane-2,4-dione), Ir (Piq) ₃ , and RD 61 from UDC. As the green phosphorescent dopant, Ir (PPy) ₂ (acac), Ir (PPy) ₃ (PPy = 2-phenylpyridine), and UD's GD48 may be used. 6-F2PPy) ₂ Irpic (Ref . Appl. Phys. Lett., 79, 2082-2084, 2001) and the like.

Accordingly, according to another embodiment of the present invention provides an organic photoelectric device comprising the compound for an organic photoelectric device. In this case, the organic photoelectric device means an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, or an organic memory device. In the case of an organic solar cell, a compound for an organic photoelectric device according to an embodiment of the present invention is included in an electrode or an electrode buffer layer to increase quantum efficiency, and in the case of an organic transistor, it may be used as an electrode material in a gate, a source-drain electrode, or the like. have.

Hereinafter, an organic photoelectric device will be described in detail. According to another embodiment of the present invention, an anode, a cathode, and at least one organic thin film layer disposed between the anode and the cathode, the organic thin film layer is an organic photoelectric device comprising the compound for the organic photoelectric device Is provided.

The organic thin film layer which may include the compound for an organic photoelectric device may be any one selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a combination thereof. One layer may be included, at least one of which includes a compound for an organic photoelectric device according to the present invention. More preferably, the compound for an organic photoelectric device according to the present invention may be included in any one layer selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, and a combination thereof.

1 to 5 are cross-sectional views of an organic photoelectric device including the compound for an organic photoelectric device according to an embodiment of the present invention.

1 to 5, an organic photoelectric device 100, 200, 300, 400, and 500 according to an embodiment of the present invention may include an anode 120, a cathode 110, and a gap between the anode and the cathode. It has a structure including at least one organic thin film layer 105 interposed therebetween.

The anode 120 includes a cathode material. As the anode material, a material having a large work function is preferably used to facilitate injection of holes into the organic thin film layer. Specific examples of the positive electrode material may include a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof, and include zinc oxide, indium oxide, indium tin oxide (ITO), and indium. Metal oxides such as zinc oxide (IZO); and combinations of metals and oxides such as ZnO and Al, or SnO ₂ and Sb; poly (3-methylthiophene), poly [3,4- ( Ethylene-1,2-dioxy) thiophene] (conductive polymers such as polyehtylenedioxythiophene (PEDT), polypyrrole and polyaniline). However, the positive electrode material is not limited to these compounds. More preferably, a transparent electrode including ITO may be used as the anode material.

The cathode 110 includes a cathode material, and the anode material is preferably a material having a small work function to facilitate electron injection into the organic thin film layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof, and LiF / Al. And multilayered structure materials such as LiO ₂ / Al, LiF / Ca, LiF / Al, and BaF ₂ / Ca. However, the negative electrode material is not limited to these compounds. More preferably, a metal electrode such as aluminum may be used as the cathode material.

First, referring to FIG. 1, FIG. 1 illustrates an organic photoelectric device 100 in which only a light emitting layer 130 exists as an organic thin film layer 105. The organic thin film layer 105 may exist only as a light emitting layer 130.

Referring to FIG. 2, FIG. 2 illustrates a two-layered organic photoelectric device 200 in which an emission layer 230 including an electron transport layer and a hole transport layer 140 exist as an organic thin film layer 105, and an organic thin film layer 105. The silver may be a two-layer type including an emission layer 230 and a hole transport layer 140. In this case, the light emitting layer 130 functions as an electron transporting layer, and the hole transporting layer 140 functions to improve the bonding property with a transparent electrode such as ITO and the hole transporting property.

Referring to FIG. 3, FIG. 3 illustrates a three-layered organic photoelectric device 300 having an electron transport layer 150, a light emitting layer 130, and a hole transport layer 140 as an organic thin film layer 105. In 105, the light emitting layer 130 is in an independent form, and has a form in which layers (electron transport layer 150 and hole transport layer 140) having excellent electron transport properties and hole transport properties are stacked in separate layers.

Referring to FIG. 4, FIG. 4 illustrates a four-layered organic photoelectric device 400 in which an electron injection layer 160, an emission layer 130, a hole transport layer 140, and a hole injection layer 170 exist as an organic thin film layer 105. ), The hole injection layer 170 may improve the adhesion to ITO used as an anode.

Referring to FIG. 5, FIG. 5 is an organic thin film layer 105, which is different from an electron injection layer 160, an electron transport layer 150, an emission layer 130, a hole transport layer 140, and a hole injection layer 170. As a five-layered organic photoelectric device 500 having five layers serving as a function, the organic photoelectric device 500 is effective in lowering voltage by separately forming an electron injection layer 160.

1 to 5, the electron transport layer 150, the electron injection layer 160, the light emitting layers 130 and 230, the hole transport layer 140, and the hole injection layer 170 forming the organic thin film layer 105, and these Any one selected from the group consisting of a combination includes the compound for an organic photoelectric device. In this case, the compound for an organic photoelectric device may be used in the electron transport layer 150 including the electron transport layer 150 or the electron injection layer 160, and the hole blocking layer (not shown) when included in the electron transport layer It is desirable to provide an organic photoelectric device having a simpler structure since there is no need to separately form).

In addition, when the compound for an organic photoelectric device is included in the light emitting layers 130 and 230, the compound for an organic photoelectric device may be included as a phosphorescent or fluorescent host, or may be included as a fluorescent blue dopant.

The above-described organic photoelectric device includes a dry film method such as vacuum deposition, sputtering, plasma plating, and ion plating after an anode is formed on a substrate; Alternatively, the organic thin film layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by forming a cathode thereon.

According to another embodiment of the present invention, a display device including the organic photoelectric device is provided.

Hereinafter, specific embodiments of the present invention will be described. However, the embodiments described below are merely for illustrating or explaining the present invention in detail, and thus the present invention is not limited thereto.

Synthesis of Compound for Organic Photoelectric Device

Example 1: Synthesis of Compound (28)

Compound (28) of Formula 5 shown as a more specific example of the compound for an organic photoelectric device of the present invention was synthesized through three steps as shown in Scheme 1 below.

[Reaction Scheme 1]

A first step; Synthesis of Intermediate Product (B)

10 g (22 mmol) of Compound (A), 4.56 g (22 mmol) of 1-bromo-2-nitrobenzene, 1.27 g (1.1 mmol) of tetrakis- (triphenylphosphine) palladium, 6.08 g (44) of potassium carbonate mmol), and 100 ml of water were suspended in 300 ml of toluene and heated to reflux for 12 hours under a nitrogen atmosphere.

After the reaction fluid was separated into two layers, the organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate.

After distilling off the organic solvent under reduced pressure, the residue was recrystallized from methanol, and the precipitated crystals were separated by filtration. The obtained residue was purified by silica gel column chromatography to give 6 g (yield: 62%) of intermediate product (B).

A second step; Synthesis of Intermediate Product (C)

6 g (14 mmol) of intermediate product (B) and 7.34 g (28 mmol) of triphenylphosphine were dissolved in 100 ml of dichlorobenzene and heated to reflux at 160 ° C. under argon atmosphere.

After distilling off the organic solvent under reduced pressure, the residue was recrystallized from methanol, and the precipitated crystals were separated by filtration. The obtained residue was purified by silica gel column chromatography to give 4 g (yield: 70%) of the intermediate product (C).

A third step; Synthesis of Compound (28)

Intermediate (C) 5 g (12 mmol), 1.94 g (18 mmol) of 1,4-bromobutylbenzene, 2.48 g (18 mmol) of potassium carbonate, and 180 mg (0.018 mmol) of cuprous chloride were added to dimethyl sulfoxide. It was suspended in 200 ml and heated to reflux for 24 hours under a nitrogen atmosphere.

After the reaction fluid was separated into two layers, the organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After distilling off the organic solvent under reduced pressure, the residue was purified by silica gel column chromatography to obtain 3.8 g (yield: 60%) of compound (28).

EA = (C, 91.5%; H, 5.8%; N, 2.6%)

Example 2: Synthesis of Compound (49)

Compound (48), which is presented as a more specific example of the material for an organic photoelectric device of the present invention, was synthesized through a one-step route using the intermediate product (C) synthesized in Example 1 as in Scheme 2 below.

[Reaction Scheme 2]

5 g (12 mmol) of intermediate (C), 4.22 g (12 mmol) of compound (D), 2.48 g (18 mmol) of potassium carbonate, and 180 mg (0.018 mmol) of cuprous chloride were suspended in 200 ml of dimethylsulfoxide. The mixture was heated to reflux for 24 hours under a nitrogen atmosphere.

After the reaction fluid was separated into two layers, the organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After distilling off the organic solvent under reduced pressure, the residue was purified by silica gel column chromatography to obtain 5.4 g (yield: 66%) of compound (49).

EA = (C 90.50%; H, 5.36%; N, 4.14%)

Example 3: Synthesis of Compound (59)

Compound (59), given as a specific example of the material for an organic photoelectric device of the present invention, was synthesized as in Scheme 3 below.

Scheme 3

First step: intermediate product (H) Synthesis of

In a 500 ml round bottom flask equipped with a thermometer, a reflux condenser and a stirrer, substance (G) (10.0 g, 22.6 mmol), 1-bromo-2-nitrobenzene (6.2 g, 24.8 mmol), and tetra Dissolve kiss- (triphenylphosphine) palladium (0.8 g, 0.69 mmol) in 200 mL tetrahydrofuran (THF), add 50 mL of 20% tetratriethylammonium hydroxide, and then 24 hours at 75 ° C. Was stirred. After the reaction, the reaction was cooled to room temperature, extracted with methylene chloride several times, and washed with water several times. Thereafter, the washed reaction product was dried with anhydrous magnesium sulfate, filtered, and then the solvent was removed. The solvent was removed and then purified through a silica gel column with a methylene chloride / hexane (1: 1 volume ratio) mixed solvent to obtain 8.5 g of an intermediate product (H) (yield: 86.0%).

Second Step: Intermediate Product (I) Synthesis of

8 g (18.2 mmol) of intermediate product (H) and 14.3 g (54.6 mmol) of triphenylphosphine were dissolved in 150 ml of dichlorobenzene and heated to reflux at 160 ° C. under argon atmosphere.

The organic solvent was distilled off under reduced pressure, dissolved in a methylene chloride furnace and washed several times with water. Thereafter, the washed reaction product was dried with anhydrous magnesium sulfate, filtered, and then the solvent was removed. The solvent was removed and then purified through a silica gel column with a methylene chloride / hexane (2: 1) mixed solvent to give 5.5 g (yield: 74.5%) of intermediate product (I) .

Third Step: Compound (59) Synthesis of

Intermediate product (I) (5 g, 12.3 mmol) is dissolved in 100 mL of anhydrous tetrahydrofuran (THF), cooled to -78 ° C and slowly added dropwise 9.2 mL (1.6M concentration) of n-BuLi. After dropping, the mixture was stirred for 30 minutes, and then heated to room temperature and stirred for 20 minutes. After the temperature was lowered to -78 ° C, 2-chloro-4,6-diphenyl triazine (3.59 g, 13.4 mmol) was added thereto, followed by stirring at room temperature for 12 hours. Water was added slowly to terminate the reaction, extracted with methylene chloride and washed several times with water. Thereafter, the washed reaction product was dried with anhydrous magnesium sulfate, filtered, and then the solvent was removed.

The reaction was recrystallized from a methylene chloride / hexane (1: 3) mixed solvent to give 3.2 g of compound (59) (yield: 40.8%).

Example 4: Synthesis of Compound (69)

Compound (69), presented as a more specific example of the material for an organic photoelectric device of the present invention, was synthesized using the intermediate product (I) synthesized in Example 3, as shown in Scheme 4 below.

[Reaction Scheme 4]

Intermediate product (I) (5 g, 12.3 mmol) synthesized in Example 3 was dissolved in 100 mL of anhydrous tetrahydrofuran (THF), cooled to -78 ° C and 9.2 mL of n-BuLi (1.6 M concentration). Slowly add dropwise. After dropping, the mixture was stirred for 30 minutes, and then heated to room temperature and stirred for 20 minutes. After the temperature was lowered to -78 ° C, 2,4-dichloro-6-phenyl triazine (1.32 g, 5.8 mmol) was added thereto, followed by stirring at room temperature for 12 hours. Water was added slowly to terminate the reaction, extracted with methylene chloride and washed several times with water. Thereafter, the washed reaction product was dried with anhydrous magnesium sulfate, filtered, and then the solvent was removed.

The reaction was recrystallized from a methylene chloride / hexane (1: 3) mixed solvent to give 2.5 g of compound (69) (yield: 44.7%).

Thermal Stability Evaluation of Compounds for Organic Photoelectric Devices

The glass transition temperature (T _g ) and pyrolysis temperature (T _d ) of the compounds for organic photoelectric devices synthesized in Examples 1 and 2 were differential scanning calorimetry (DSC) and thermogravimetry (TGA). Was measured. The results are shown in Table 1 below.

Fabrication of Organic Photoelectric Device

Example 5

An organic photoelectric device was manufactured by using Compound (28) synthesized in Example 1 as a host and Ir (PPy) ₃ as a dopant. ITO was used as a cathode of 1000 kPa, and aluminum (Al) was used as a cathode of 1000 kPa.

Specifically, the manufacturing method of the organic photoelectric device, the anode is 15 ITO glass substrate with sheet resistance of / cm ² was cut into 50 mm X 50 mm X 0.7 mm and ultrasonically cleaned in acetone, isopropyl alcohol and pure water for 15 minutes, and then UV ozone cleaning for 30 minutes. Was used.

N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolylamino) -phenyl) at a vacuum degree of 650 × 10 ⁻⁷ Pa and a deposition rate of 0.1 to 0.3 nm / s on the substrate. ] -Biphenyl-4,4'-diamine (N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl-4,4'-diamine : DNTPD) (60 nm), and N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine (NPB) (30 nm) were deposited to form a 900 kV hole transport layer.

Subsequently, a light emitting layer having a film thickness of 300 Pa was formed using the compound (28) prepared in Example 1 under the same vacuum deposition conditions. At this time, a phosphorescent dopant Ir (PPy) ₃ was simultaneously deposited. At this time, by adjusting the deposition rate of the phosphorescent dopant, when the total amount of the light emitting layer is 100% by weight, it was deposited so that the compounding amount of the phosphorescent dopant was 5% by weight.

BAlq was deposited on the emission layer using the same vacuum deposition condition to form a hole blocking layer having a thickness of 50 Å.

Subsequently, Alq ₃ was deposited under the same vacuum deposition conditions to form an electron transport layer having a film thickness of 200 GPa.

An organic photoelectric device was manufactured by sequentially depositing LiF and Al as a cathode on the electron transport layer.

The structure of the organic photoelectric device is ITO / DNTPD (60 nm) / NPB (30 nm) / EML (Compound (28) + Ir (PPy) ₃ , 30 nm) / Balq (5 nm) / Alq ₃ (20 nm) / LiF / Al (100 nm) was produced in a nine-layer structure.

Example 6

In forming a light emitting layer having a film thickness of 300 Pa using the compound (28) prepared in Example 1, the compounding amount of the phosphorescent dopant was adjusted by adjusting the deposition rate of the phosphorescent dopant to 100% by weight of the total light emitting layer. An organic photoelectric device was manufactured according to the same method as Example 5 except for depositing the same to 7.5 wt%.

Example 7

In forming a light emitting layer having a film thickness of 300 Pa using the compound (28) prepared in Example 1, the compounding amount of the phosphorescent dopant was adjusted by adjusting the deposition rate of the phosphorescent dopant to 100% by weight of the total light emitting layer. An organic photoelectric device was manufactured according to the same method as Example 5 except for depositing the same as 10 wt%.

Comparative Example 1

An organic photoelectric device was manufactured in the same manner as in Example 7, except that 4,4-N, N-dicarbazolebiphenyl (CBP) represented by Chemical Formula 6 was used instead of Compound (28) as a host. It was.

[Formula 6]

Example 8

An organic photoelectric device was manufactured by using Compound (28) synthesized in Example 1 as a host and Ir (Piq) ₂ acac as a dopant. ITO was used as the cathode at a thickness of 1000 kPa, and aluminum (Al) was used as the cathode at a thickness of 1000 kPa.

Specifically, the method of manufacturing an organic photoelectric device, the anode is cut into a size of 50 mm X 50 mm X 0.7 mm ITO glass substrate having a sheet resistance value of 15 Ω / cm ² to acetone, isopropyl alcohol and pure water inside Ultrasonic cleaning was performed for 15 minutes each, followed by UV ozone cleaning for 30 minutes.

DNTPD (60 nm) and NPB (30 nm) were deposited on the substrate at a vacuum degree of 650 × 10 ⁻⁷ Pa, and a deposition rate of 0.1 to 0.3 nm / s to form a hole transport layer of 900 kPa.

Subsequently, using the compound (28) prepared in Example 1 under the same vacuum deposition conditions to form a light emitting layer having a film thickness of 300 kPa, at this time, the phosphorescent dopant Ir (Piq) ₂ acac was deposited at the same time. At this time, by adjusting the deposition rate of the phosphorescent dopant, when the total amount of the light emitting layer is 100% by weight, it was deposited so that the compounding amount of the phosphorescent dopant was 5% by weight.

A Batocuproin (BCP) layer was deposited on the light emitting layer using the same vacuum deposition conditions to form a hole blocking layer having a thickness of 50 Å.

Subsequently, Alq ₃ was deposited under the same vacuum deposition conditions to form an electron transport layer having a film thickness of 200 GPa.

 An organic photoelectric device was manufactured by sequentially depositing LiF and Al as a cathode on the electron transport layer.

The structure of the organic photoelectric device is ITO / DNTPD (60 nm) / NPB (30 nm) / EML (Compound (28) + Ir (Piq) ₂ acac, 30 nm) / BCP (5 nm) / Alq ₃ (20 nm) 9 layer of LiF / Al (100 nm).

Example 9

In forming a light emitting layer having a film thickness of 300 Pa using the compound (28) prepared in Example 1, the compounding amount of the phosphorescent dopant was adjusted by adjusting the deposition rate of the phosphorescent dopant to 100% by weight of the total light emitting layer. An organic photoelectric device was manufactured in the same manner as in Example 8, except that the weight thereof was set to 7.5 wt%.

Example 10

In forming a light emitting layer having a film thickness of 300 Pa using the compound (28) prepared in Example 1, the compounding amount of the phosphorescent dopant was adjusted by adjusting the deposition rate of the phosphorescent dopant to 100% by weight of the total light emitting layer. An organic photoelectric device was manufactured according to the same method as Example 8 except for depositing the same as 10 wt%.

Comparative Example 2

An organic photoelectric device was manufactured in the same manner as in Example 10, except that 4,4-N, N-dicarbazolebiphenyl (CBP) represented by Chemical Formula 6 was used instead of the compound (28) as a host. It was.

Performance Measurement of Organic Photoelectric Devices

For each organic photoelectric device manufactured in Examples 5 to 10 and Comparative Examples 1 to 2, current density change, luminance change, and luminous efficiency according to voltage were measured. Specific measurement methods are as follows, and the results are shown in Table 1 below.

1) Measurement of change of current density according to voltage change

With respect to the manufactured organic electroluminescent device, the current value flowing through the unit device was measured by using a current-voltmeter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain a result. .

2) Measurement of luminance change according to voltage change

The luminance of the organic electroluminescent device was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V to obtain a result.

3) Luminous efficiency measurement

The luminous efficiency was calculated using the luminance value, the current density, and the voltage (V) measured in the "1) change of current density according to voltage change" and "2) measurement of brightness change according to voltage change".

[Table 1]

division Host material 2000 nit The driving voltage (V) Luminous Efficiency (lm / W) Color coordinates
(x, y) Example 5 Compound (28) 7.5 19.7 0.30, 0.62 Example 6 Compound (28) 7.4 20.2 0.30, 0.62 Example 7 Compound (28) 7.3 21.3 0.30, 0.62 Comparative Example 1 CBP 8.0 18.2 0.30, 0.62

Referring to Table 1, it is confirmed that the organic photoelectric device according to Examples 5 to 7 has a driving voltage of 7.5V or less at a luminance of 2000 nit and a lower driving voltage than the 8.0V driving voltage of the organic photoelectric device of Comparative Example 1. Could. In addition, the organic photoelectric device according to Examples 5 to 7 exhibited characteristics equal to or greater than those of the organic photoelectric device of Comparative Example 1 in terms of luminous efficiency and color coordinate characteristics.

[Table 2]

division Host material 1000 nit The driving voltage (V) Luminous Efficiency (lm / W) Color coordinates
(x, y) Example 8 Compound (28) 8.5 14.2 0.67, 0.34 Example 9 Compound (28) 8.3 14.8 0.67, 0.34 Example 10 Compound (28) 8.0 15.2 0.67, 0.34 Comparative Example 2 CBP 8.7 13.2 0.67, 0.34

Referring to Table 2, the organic photoelectric device according to Examples 8 to 9 has a driving voltage of 8.5 V or less at a luminance of 1000 nit, and a lower driving voltage than that of 8.7 V of the organic photoelectric device of Comparative Example 2. Could. In addition, the organic photoelectric device according to Examples 8 to 9 exhibited characteristics equal to or greater than those of the organic photoelectric device of Comparative Example 2 in terms of luminous efficiency and color coordinate characteristics.

The present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

1 to 5 are cross-sectional views illustrating various embodiments of an organic photoelectric device that may be manufactured including a compound for an organic photoelectric device according to an embodiment of the present invention.

<Explanation of symbols for main parts of the drawings>

100: organic photoelectric device 110: cathode

120: anode 105: organic thin film layer

130: light emitting layer 140: hole transport layer

150: electron transport layer 160: electron injection layer

170: hole injection layer 230: light emitting layer + electron transport layer

Claims (12)

A compound for an organic photoelectric device represented by Formula 1 below: [Formula 1]

In Formula 1, A ₁ is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 hetero arylene group; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; NR, wherein R is hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; a group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms Is selected from the group consisting of), A ₂ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 heteroaryl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; NR'R ", wherein R 'and R" are each independently hydrogen, substituted or unsubstituted aryl group having 6 to 30 carbon atoms; substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; substituted or unsubstituted Selected from the group consisting of alkyl groups having 1 to 30 carbon atoms. R _a to R _e are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted lower alkyl group having 1 to 10 carbon atoms, carbazolyl group or arylamine group having 6 to 20 carbon atoms, Provided that at least one selected from A ₁ and A ₂ includes an aromatic ring, n is an integer of 0 to 3, provided that when A is an integer of 2 or more, A ₁ may be the same or different from each other. The method of claim 1, In Formula 1, A ₁ is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, A ₂ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or NR'R ", wherein R 'and R" are each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; substituted or unsubstituted It is selected from the group consisting of an alkyl group having 1 to 30 ring carbon atoms.) Compound for an organic photoelectric device. The method of claim 1, The compound for an organic photoelectric device is a compound for an organic photoelectric device is represented by the following formula (2): [Formula 2]

In Chemical Formula 2 A ₁ is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 hetero arylene group; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; NR, wherein R is hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; a group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms Is selected from the group consisting of), X is N, R ₁ and R ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 heteroaryl group; And it is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, wherein R ₁ and R ₂ may form a fusion ring, R _a to R _e are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted lower alkyl group having 1 to 10 carbon atoms, carbazolyl group or arylamine group having 6 to 20 carbon atoms, Provided that at least one selected from A ₁ , R _1, and R ₂ includes an aromatic ring, n is an integer of 1 to 3, provided that when n is an integer of 2 or more, two or more A ₁ may be the same or different from each other. The method of claim 1, The compound for an organic photoelectric device is a compound for an organic photoelectric device is represented by the following formula (3): (3)

In Chemical Formula 3 A ₁ , A ₃ and A ₄ are the same as or different from each other, and each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 hetero arylene group; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; NR, wherein R is hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; a group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms Is selected from the group consisting of), X, Y and Z are N, R ₃ to R ₆ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 heteroaryl group; And it may be selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, wherein R ₃ to R ₆ may form a fusion ring, R _a to R _e are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted lower alkyl group having 1 to 10 carbon atoms, carbazolyl group or arylamine group having 6 to 20 carbon atoms, Provided that at least one selected from A ₁ , A ₃ , A _4, and R ₃ to R ₆ includes an aromatic ring, n is an integer of 1 to 3, provided that when n is an integer of 2 or more, two or more A ₁ may be the same or different from each other. The method of claim 1, The compound for an organic photoelectric device is a compound for an organic photoelectric device is represented by the following formula (4): [Formula 4]

In Chemical Formula 4 A ₁ is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Substituted or unsubstituted C2-C30 hetero arylene group; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; NR, wherein R is hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; a group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms Is selected from the group consisting of), R _a to R _j are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted lower alkyl group having 1 to 10 carbon atoms, carbazolyl group or arylamine group having 6 to 20 carbon atoms, n is an integer of 1 to 3, provided that when n is an integer of 2 or more, two or more A ₁ may be the same or different from each other. The method of claim 1, The compound for an organic photoelectric device is a compound represented by Formula 5 or a mixture thereof: [Chemical Formula 5]

The method of claim 1, The compound for an organic photoelectric device may be used as a charge transport material or a host material. The method of claim 1, The compound for an organic photoelectric device has a glass transition temperature (T _g ) of 120 ℃ or more, the thermal decomposition temperature (T _d ) of the compound for an organic photoelectric device 400 ℃. anode; cathode; And an organic thin film layer interposed between the anode and the cathode. The organic thin film layer is an organic photoelectric device comprising a compound for an organic photoelectric device according to any one of claims 1 to 8. 10. The method of claim 9, The organic thin film layer is selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron blocking layer and combinations thereof. 10. The method of claim 9, The organic thin film layer is an organic photoelectric device further comprises a dopant. 12. The method of claim 11, The dopant is an organic photoelectric device that is a phosphorescent dopant of red, green, blue, or white.

Images