WO2020130456A1 - Compound for organic electric element, organic electric element using same, and electronic device comprising organic electric element - Google Patents

Abstract

The present invention relates to a compound for an organic electric element, an organic electric element using same, and an electronic device comprising the organic electric element. According to the present invention, the luminous efficiency of an organic electric element can be increased, the driving voltage of the element can be reduced, and the service life of the element can be improved.

Description

Compound for organic electric element, organic electric element using same, and electronic device thereof

The present invention relates to a compound for an organic electric element, an organic electric element using the same, and an electronic device thereof.

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

Materials used for the organic material layer in the organic electric device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function.

In addition, the light emitting material may be classified into a high molecular weight type and a low molecular weight type according to the molecular weight, and may be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron according to the light emission mechanism. Can. In addition, the luminescent material may be divided into blue, green, and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color according to the luminous color.

On the other hand, when only one material is used as the light emitting material, the problem of the maximum light emission wavelength shifting to a long wavelength due to intermolecular interaction and a decrease in color purity or a decrease in the efficiency of the device due to the light emission attenuation effect, increases color purity and energy transfer In order to increase the luminous efficiency through, a host/dopant system may be used as a luminescent material. The principle is that when a small amount of the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with the light emitting layer, exciton generated in the light emitting layer is transported as a dopant to produce light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of the dopant used.

Currently, the portable display market is increasing in size with a large-area display. Since the portable display has a battery that is a limited power supply, more efficient power consumption is required than the power consumption required in the existing portable display. In addition, in addition to efficient power consumption, luminous efficiency and lifetime issues must also be solved.

Efficiency, life, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic substances due to Joule heating generated during driving decreases, and as a result, It shows a tendency to increase life. However, simply improving the organic layer does not maximize efficiency. This is because long life and high efficiency can be achieved at the same time when the optimum combination of energy level and T1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) is achieved. Therefore, there is a need to develop a light emitting material having high thermal stability and efficiently achieving charge balance in the light emitting layer.

That is, in order to sufficiently exhibit the excellent characteristics of the organic electric device, materials constituting an 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, a light emitting auxiliary layer material, are stable and efficient Although it should be preceded by the material, the development of a stable and efficient organic material layer material for an organic electric device has not been sufficiently achieved.

An object of the present invention is to provide a compound capable of improving the device's high luminous efficiency, low driving voltage, high heat resistance, color purity and lifetime, and an organic electric device using the same and its electronic device.

In one aspect, the present invention provides a compound represented by the formula below.

In another aspect, the present invention provides an organic electric device using the compound represented by the formula and an electronic device thereof.

By using the compound according to the present invention it is possible to achieve a high luminous efficiency of the device, a low driving voltage, there is an effect that can improve the life of the device.

1 is a cross-sectional view of an organic light emitting device according to an embodiment of the present invention.

2 is an exemplary view of an electronic device according to an embodiment of the present invention.

3 and 4 are exciton life measurement results of Examples and Comparative Examples.

5 is a result of measuring luminance according to wavelength bands of Examples and Comparative Examples.

6 is a result of measuring the oscillator strength of Examples and Comparative Examples.

7 and 8 are HOMO and LUMO simulation results of Examples and Comparative Examples

Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

In adding reference numerals to the components of each drawing, it should be noted that the same components are given the same reference numerals as possible, even if they are displayed on different drawings. In addition, in describing the present invention, when it is determined that detailed descriptions of related well-known structures or functions may obscure the subject matter of the present invention, detailed descriptions thereof will be omitted.

In addition, in describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only for distinguishing the component from other components, and the nature, order, or order of the component is not limited by the term. When a component is described as being "connected", "coupled" or "connected" to another component, the component may be directly connected to or connected to the other component, but another component between each component It will be understood that elements may be "connected", "coupled" or "connected".

Also, if a component such as a layer, film, region, plate, etc. is said to be "above" or "on" another component, it is not only when the other component is "directly above", but also with another component in the middle. It should be understood that the case may be included. Conversely, it should be understood that when a component is said to be “just above” another part, it means that there is no other part in between.

Terms used in this specification and in the appended claims are as follows, unless stated otherwise.

The term "halo" or "halogen" as used herein includes fluorine (F), chlorine (Cl), bromine (Br), and iodine (I), unless otherwise noted.

The term "alkyl" or "alkyl group" as used herein has 1 to 60 carbons connected by a single bond, unless otherwise specified, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted By radicals of saturated aliphatic functional groups, including cycloalkyl groups, cycloalkyl-substituted alkyl groups.

As used herein, the term “haloalkyl group” or “halogenalkyl group” means an alkyl group substituted with halogen unless otherwise specified.

As used herein, the terms "alkenyl" or "alkynyl" have a double or triple bond, respectively, unless otherwise specified, including straight or branched chain groups, and having from 2 to 60 carbon atoms, It is not limited.

As used herein, the term "cycloalkyl" means an alkyl forming a ring having 3 to 60 carbon atoms, and is not limited thereto.

As used herein, the term "alkoxy group" or "alkyloxy group" refers to an alkyl group to which an oxygen radical is bonded, and has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.

As used herein, the terms "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" means an alkenyl group to which an oxygen radical is attached, 2 to 60 unless otherwise specified. Has carbon number, but is not limited thereto.

The terms "aryl group" and "arylene group" as used herein have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto. In this specification, an aryl group or an arylene group includes monocyclic, ring aggregates, conjugated several ring systems, compounds, and the like. For example, the aryl group may refer to a phenyl group, a monovalent functional group of biphenyl, a monovalent functional group of naphthalene, a fluorenyl group, or a substituted fluorenyl group.

As used herein, the terms "fluorenyl group" or "fluorenylene group" means a monovalent or divalent functional group of fluorene, respectively, unless otherwise specified, and "substituted fluorenyl group" or "substituted flu. Orenylene group" means a monovalent or divalent functional group of substituted fluorene, and "substituted fluorene" means at least one of the following substituents R, R', R", R'" is a functional group other than hydrogen Means that R and R'are bonded to each other to form a compound as a spy together with the carbon to which they are bonded.

In addition, R, R', R" and R"' are each independently an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, 3 It may be a heterocyclic group having a carbon number of 30 to 30, for example, the aryl group may be phenyl, biphenyl, naphthalene, anthracene or phenanthrene, the heterocyclic group pyrrole, furan, thiophene, pyrazole, imidazole , Triazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, indole, benzofuran, quinazoline or quinoxaline, for example, the substituted fluorenyl group and fluorylene group are 9,9, respectively. It may be a monovalent or divalent functional group of -dimethylfluorene, 9,9-diphenylfluorene and 9,9'-spyrobi[9H-fluorene].

The term "ring assemblies" as used herein refers to two or more ring systems (single or fused ring systems) directly connected to each other through a single bond or a double bond, and directly between such rings. This means that the number of linkages is one less than the total number of ring systems in this compound. Ring aggregates may have the same or different ring systems connected directly to each other through single or double bonds.

Since the aryl group includes a ring aggregate in the present specification, the aryl group includes biphenyl and terphenyl in which a benzene ring, which is a single aromatic ring, is connected by a single bond. In addition, since the aryl group also includes a compound in which the aromatic ring system bonded to the aromatic single ring is connected by a single bond, for example, fluorene, an aromatic ring system bonded to a benzene ring, which is an aromatic single ring, is conjugated to a pie electron system ( Compounds linked to form conjugated pi electron systems) are also included.

As used herein, the term "conjugated multiple ring system" refers to a fused ring form sharing at least two atoms, and a ring system of two or more hydrocarbons is a conjugated form and at least one heteroatom is included. And a heterocyclic system in which at least one is conjugated. These conjugated several ring systems can be aromatic rings, heteroaromatic rings, aliphatic rings or combinations of these rings.

The term "spiro compound" as used herein has a'spiro union', and a spiro linkage refers to a link made by two rings sharing only one atom. At this time, the atoms shared in the two rings are called'spyro atoms', and these are'monospyro-','dispiro-','trispyro' depending on the number of spy atoms in a compound, respectively. It is called a compound.

As used herein, the term “heterocyclic group” includes aromatic rings such as “heteroaryl group” or “heteroarylene group” as well as non-aromatic rings, and carbon atoms each containing one or more heteroatoms unless otherwise specified. It means a ring of 2 to 60, but is not limited thereto. As used herein, the term "heteroatom" refers to N, O, S, P or Si, unless otherwise specified, and the heterocyclic group is a monocyclic, ring aggregate containing heteroatoms, multiple fused ring systems, spies Means a compound and the like.

In addition, "heterocyclic group" may include a ring containing SO ₂ instead of carbon forming a ring. For example, "heterocyclic group" includes the following compounds.

The term "ring" as used herein includes monocyclic and polycyclic, includes hydrocarbon rings as well as heterocycles containing at least one heteroatom, and includes aromatic and non-aromatic rings.

The term "polycyclic" as used herein includes ring assemblies, fused multiple ring systems and spiro compounds, such as biphenyls, terphenyls, aromatics as well as non-aromatics, and hydrocarbons. Rings include, of course, heterocycles comprising at least one heteroatom.

In addition, when the prefix is named consecutively, it means that the substituents are listed in the order described first. For example, in the case of an arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of an alkoxycarbonyl group, it means a carbonyl group substituted with an alkoxy group, and in the case of an arylcarbonyl alkenyl group, it means an alkenyl group substituted with an arylcarbonyl group, wherein An arylcarbonyl group is a carbonyl group substituted with an aryl group.

Also, unless expressly stated, the term "substituted" in the term "substituted or unsubstituted" as used herein is deuterium, halogen, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkylamine group, C ₁ -C ₂₀ alkylthiophene group, C ₆ -C ₂₀ arylthiophene group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, C ₈ -C ₂₀ aryl alkenyl group, a silane group, a boron Means a group, a germanium group, and one or more substituents selected from the group consisting of C ₂ -C ₂₀ heterocyclic groups including at least one hetero atom selected from the group consisting of O, N, S, Si and P And is not limited to these substituents.

In the present specification, the'functional group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituent may describe'the name of a functional group reflecting a singer', but is described as a'parent compound name'. You may. For example, in the case of'phenanthrene', which is a kind of aryl group, the monovalent'group' is'phenanthryl (group)' and the divalent group is'phenanthrylene (group)', so that the singer is classified and the name of the group is described. It can be done, but it can be described as the parent compound name'phenanthrene' regardless of the singer. Similarly, in the case of pyrimidine, regardless of the valence, it is described as'pyrimidine', or in the case of monovalent, pyrimidinyl (group), in the case of divalent, pyrimidineylene (group), etc. It may be written as'name'. Accordingly, in the present specification, when the type of a substituent is described as a parent compound name, it may mean an n-valent'group' formed by detaching a hydrogen atom bonded to a carbon atom and/or a heteroatom of the parent compound.

In addition, unless expressly stated, the formula used herein is the same as the definition of a substituent based on the exponent definition of the following formula.

Here, when a is 0, the substituent R ¹ is absent, when a is 1, one substituent R ¹ is bound to any one of carbons forming a benzene ring, and when a is 2 or 3, respectively At the same time, R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it binds to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bound to the carbon forming the benzene ring is omitted. .

In this specification, the substituents are bonded to each other to form a ring, a plurality of substituents bonded to each other is a carbon atom; It means to form a saturated or unsaturated ring by sharing at least one atom of the heteroatoms O, N, S, Si and P. For example, in the case of naphthalene, an adjacent methyl group and a butadienyl group substituted in one benzene ring share one carbon to form an unsaturated ring, or a vinyl group and a propylene group share one carbon to make it unsaturated. It can be regarded as forming a ring. In addition, in the case of fluorene, it can be regarded as an aryl group having 13 carbon atoms in itself, but it can also be seen that two methyl groups substituted with a biphenyl group are bonded to each other so as to share one carbon to form a ring.

1 is an exemplary view of an organic electric device according to an embodiment of the present invention.

Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180 and a first electrode 110 and a second electrode 180 formed on the substrate 110. ) Between the organic material layer comprising the compound according to the present invention. In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may sequentially include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160 and an electron injection layer 170 on the first electrode 120. At this time, at least one of these layers may be omitted, or a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like may be further included, and the electron transport layer 160, etc., serves as a hole blocking layer. You could do it.

In addition, although not shown, the organic electric device according to the present invention may further include a protective layer or a light efficiency improving layer (Capping layer) formed on one surface opposite to the organic material layer among at least one surface of the first electrode and the second electrode.

The compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, an electron injection layer 170, a light emitting layer 150, a light efficiency improving layer, a light emitting auxiliary layer, etc. It can be used as a material. In one example, the compound of the present invention may be used as a light emitting auxiliary layer 151 and/or a light emitting layer 150 material.

On the other hand, even in the same core, the band gap, electrical properties, and interfacial properties may vary depending on which substituent is attached to which position, so the selection of the core and the combination of sub-substituents attached thereto are very important. When an optimum combination of energy level and T ₁ value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) is achieved, long life and high efficiency can be simultaneously achieved.

As already described, in order to solve the light emission problem in the hole transport layer in the recent organic electroluminescent device, it is preferable to form an auxiliary light emitting layer between the hole transport layer and the light emitting layer, and correspond to each light emitting layer (R, G, B) Therefore, it is necessary to form different light-emitting auxiliary layers. In other words, the red light-emitting layer includes a red light-emitting layer, a green light-emitting layer, a red light-emitting auxiliary layer corresponding to a blue light-emitting layer, a green light-emitting auxiliary layer, and a blue light-emitting auxiliary layer. On the other hand, in the case of the light-emitting auxiliary layer, since it is necessary to grasp the relationship between the hole transport layer and the light-emitting layer (host), even if a similar core is used, it will be very difficult to infer the characteristics of the organic layer used.

Therefore, by forming a light emitting layer, a hole transport layer and/or a light emitting auxiliary layer using the compound according to Formula 1 of the present invention, the energy level (level) and T ₁ value between each organic material layer, the intrinsic properties (mobility, interfacial properties, etc.) By optimizing and the like, the life and efficiency of the organic electric device can be simultaneously improved.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It may be manufactured using a deposition method such as Physical Vapor Deposition (PVD) or Chemical Vapor Deposition (CVD), for example, by depositing a metal or conductive metal oxide or an alloy thereof on a substrate to form the anode 120 Then, an organic material layer including a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160 and an electron injection layer 170 is formed thereon, and then, as a cathode 180 thereon, It can be produced by depositing a material that can be used. In addition, a light-emitting auxiliary layer 151 may be additionally formed between the hole transport layer 140 and the light-emitting layer 150.

In addition, the organic material layer is a solution process or a solvent process using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, a doctor blading process, It can be produced with fewer layers by a method such as a screen printing process or a thermal transfer method. Since the organic material layer according to the present invention can be formed in various ways, the scope of the present invention is not limited by the formation method.

The organic electric device according to the present invention may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.

WOLED (White Organic Light Emitting Device) has the advantage of being easy to realize high resolution and having excellent processability, and can be manufactured using the color filter technology of the existing LCD. Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Typically, R (Red), G (Green), B (Blue) light-emitting parts are arranged in a mutually planar side-by-side manner, and a stacking method in which R, G, and B light-emitting layers are stacked vertically. There is a color conversion material (CCM) method using electroluminescence by the blue (B) organic light-emitting layer and photo-luminescence of an inorganic phosphor using light therefrom. May be applied to such WOLED.

In addition, the organic electric device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoreceptor (OPC), an organic transistor (organic TFT), a monochromatic or white lighting device.

2 is an exemplary view of an electronic device according to another embodiment of the present invention.

The electronic device 200 may include an electronic device including a display device 210 including the above-described organic electric element 230 of the present invention and a control unit 220 controlling the display device. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game machines, various TVs, and various computers.

The control unit 220 applies a driving voltage and/or signal to the organic electric device, for example, a plurality of gate lines, a gate driving circuit driving the gate lines, a plurality of data lines, and the data lines It may include a data driving circuit for driving the controller and for controlling the gate driving circuit and the data driving circuit.

The controller supplies various control signals to the data driving circuit and the gate driving circuit to control the data driving circuit and the gate driving circuit.

Hereinafter, a compound according to an aspect of the present invention will be described. The compound according to an aspect of the present invention is represented by Formula 1 below.

<Formula 1>

Hereinafter, R ₁ to R ₁₈ , Ar ₁ and Ar ₂ described in Chemical Formula 1 will be described.

R ₁ to R ₁₈ are each hydrogen, deuterium, halogen, C ₆ ~ C ₆₀ aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And aryloxy groups of C ₆ to C ₃₀ .

The fact that R ₁ to R ₁₈ are each selected from the substituents listed above means that R ₁ to R ₁₈ may be the same or different from each other.

When R ₁ to R ₁₈ are alkyl groups, R ¹ may be a C ₁ to C ₃₀ alkyl group, a C ₁ to C ₂₀ alkyl group, or a C ₁ to C ₁₀ alkyl group, for example, the alkyl group is C 1 to C10 may be a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl group, an alkyl-substituted cycloalkyl group, or a cycloalkyl-substituted alkyl group.

When R ₁ to R ₁₈ are aryl groups, R ¹ may be a C ₆ to C ₄₀ aryl group, C ₆ to C ₃₀ aryl groups, or C ₆ to C ₂₀ aryl groups, for example, benzene and naphthalene. , Anthracene, phenanthrene, tetracene, benzoanthracene, triphenylene, biphenyl, terphenyl and substituted or unsubstituted fluorene.

R ₁ to R ₁₈ may be bonded to each other to form a ring.

The R ₁ to R ₅ and R ₁₀ to R ₁₄ are preferably C ₆ to C ₂₄ aryl groups or hydrogen, and more preferably C ₆ to C ₁₂ aryl groups or hydrogen, respectively.

Ar ₁ and Ar ₂ are each C ₆ ~ C ₆₀ aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; A substituent represented by the following formula (2); A substituent represented by the following formula (3); And a substituent represented by the following Chemical Formula 4. Ar ₁ and Ar ₂ are each selected from the substituents listed above, which means that Ar ₁ and Ar ₂ may be the same or different from each other.

<Formula 2>

<Formula 3>

<Formula 4>

Hereinafter, Y, R ₁₉ to R ₂₆ , Ar ₃ to Ar ₆ described in Chemical Formulas 2 to 4 will be described.

The Y may be O or N-Ar ₆ .

Ar ₃ to Ar ₆ are each C ₆ to C ₆₀ aryl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And it may be selected from a fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60.

Ar ₃ to Ar ₆ being selected from the above substituents means that Ar ₃ to Ar ₆ may be the same or different from each other.

When Ar ₃ to Ar ₆ are aryl groups, Ar ₃ to Ar ₆ may be C ₆ to C ₄₀ aryl groups, C ₆ to C ₃₀ aryl groups, or C ₆ to C ₂₀ aryl groups, for example, Ar ₃ to Ar ₆ may be selected from benzene, naphthalene, anthracene, phenanthrene, tetracene, benzoanthracene, triphenylene, biphenyl, terphenyl and substituted or unsubstituted fluorene, respectively.

R ₁₉ to R ₂₆ are each hydrogen, deuterium, halogen, cyano group, nitro group, C ₆ to C ₆₀ aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And aryloxy groups of C ₆ to C ₃₀ .

R ₁₉ to R ₂₆ may be bonded to each other to form a ring.

When R ₁₉ to R ₂₆ are alkyl groups, R ¹ may be an alkyl group of C ₁ to C _30, an alkyl group of C ₁ to C ₂₀ , or an alkyl group of C ₁ to C ₁₀ , for example, the alkyl group is C1 to C10 may be a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl group, an alkyl-substituted cycloalkyl group, or a cycloalkyl-substituted alkyl group.

When R ₁₉ to R ₂₆ are aryl groups, R ¹ may be an aryl group of C ₆ to C _40, an aryl group of C ₆ to C ₃₀ , or an aryl group of C ₆ to C ₂₀ , for example, benzene, naphthalene , Anthracene, phenanthrene, tetracene, benzoanthracene, triphenylene, biphenyl, terphenyl and substituted or unsubstituted fluorene.

At least one of Ar ₁ and Ar ₂ may be selected from substituents represented by Formulas 2 to 4 described above. When at least one of Ar ₁ and Ar ₂ is a substituent represented by Chemical Formulas 2 to 4 described above, the compound represented by Chemical Formula 1 may provide an organic electric device having more excellent luminous efficiency and lifetime.

Preferably, any one of Ar ₁ and Ar ₂ may be selected from substituents represented by Chemical Formulas 2 to 4. That is, only one of Ar ₁ and Ar ₂ is represented by Formulas 2 to 4, and the other one may be a substituent not represented by Formulas 2 to 4. When only one of Ar ₁ and Ar ₂ is represented by Chemical Formulas 2 to 4, the compound represented by Chemical Formula 1 can provide an organic electric device having more excellent luminous efficiency and lifetime.

In R ₁ to R ₂₆ and Ar ₁ to Ar ₆ , the aliphatic hydrocarbon group, aryl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, each deuterium; Nitro group; Nitrile group; Halogen group; Amino group; A silane group unsubstituted or substituted with an alkyl group of C ₁ to C ₂₀ or an aryl group of C ₆ to C ₂₀ ; Siloxane groups; C ₁ ~ C ₂₀ alkylthio; C ₁ ~ C ₂₀ Alkoxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ aryl alkenyl group may be further substituted with one or more substituents selected from the group consisting of, and also these substituents may combine with each other to form a ring.

When the compound of Formula 1 is used in the organic material layer of the organic electronic device, an organic electrical device having excellent luminous efficiency and lifetime can be manufactured.

The compound represented by Formula 1 may be any one of the following compounds, but is not limited thereto.

As another embodiment, the present invention provides an organic electric device containing the compound represented by the formula (1).

The organic electric device includes a first electrode; A second electrode; And an organic material layer positioned between the first electrode and the second electrode. The organic material layer may include a compound represented by Chemical Formula 1, and the compound represented by Chemical Formula 1 may be a hole injection layer or a hole in the organic material layer. It may be contained in at least one of the transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer.

That is, the compound represented by Chemical Formula 1 may be used as a material for a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, or an electron injection layer.

In another embodiment, the present invention includes at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer of the organic material layer, the compound includes at least one kind It provides an organic electric device characterized in that the.

In other words, each layer may include a compound corresponding to Formula 1 alone, a mixture of two or more compounds of Formula 1, and a mixture of a compound represented by Formula 1 and a compound not corresponding to the present invention. This can be included. Here, the compound not corresponding to the present invention may be a single compound, or may be two or more compounds. At this time, when the compound is contained in a combination of two or more different compounds, the other compound may be a known compound of each organic layer, or a compound to be developed in the future. At this time, the compound contained in the organic material layer may be composed of only the same kind of compound, but may also be a mixture of two or more heterogeneous compounds represented by Chemical Formula 1.

For example, in the organic material layer, two types of compounds having different structures from each other may be mixed in a molar ratio of 99:1 to 1:99.

In another embodiment of the present invention, the present invention is a light efficiency improving layer formed on at least one side of the one side of the first electrode opposite to the organic layer or one side of the second electrode opposite to the organic layer. It provides an organic electrical device further comprising a.

Hereinafter, examples of the synthesis of the compound represented by Chemical Formula 1 according to the present invention and the manufacturing example of the organic electric device will be specifically described with reference to Examples, but the present invention is not limited to the following Examples.

[Synthesis example]

The compound represented by Chemical Formula 1 according to the present invention is synthesized by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below, but is not limited thereto.

In the following Reaction Scheme 1, Ar ₁ , Ar ₂ and R ₁ to R ₁₈ are the same as those described in the part related to Formula 1, and Pd ₂ (dba) ₃ described in the Synthesis Example of the present specification is Tris(dibenzylideneacetone)dipalladium(0) to be.

<Scheme 1>

I. Synthesis Example of Sub 1

ICZ-1-1, which is an example of Sub 1 of Scheme 1, may be formed by the following reaction.

<Reaction Scheme 2>

After dissolving indole (300.0 mg, 2.56 mmol) and benzaldehyde (271.8 mg, 2.56 mol) in acetonitrile (1.5 mL), N,2-dibromo-6-chloro-3,4-dihydro-2H-benzo[e] [1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide (DCDBTSD) (8.17 g, 0.018 mmol) was added thereto, and the mixture was refluxed and stirred at 70° C. for 24 hours. After the solution was brought down to room temperature, acetonitrile was removed and the mixture was dissolved with dimethylformamide (1.5 mL). Then, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (29 mg, 0.128 mmol) was added dropwise and stirred at reflux at 140°C for 48 hours. Upon completion of the reaction, the solution was lowered to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography using dimethyl chloride and n-hexane to obtain the intermediate (ICZ1-1') (523.0 mg, 72%).

<Scheme 3>

Dissolve the intermediate (ICZ1-1') (200 mg, 0.49 mmol) and iodobenzene (0.60 mL, 0.54 mmol) in DMPU (5 mL), potassium carbonate (203.0 mg, 1.47 mmol) and 18-crown-6 ( 38.8 mg, 0.15 mmol) was added dropwise, followed by stirring at room temperature in a nitrogen atmosphere for 30 minutes. After heating to 70° C. and stirring for 10 minutes, CuI (9.3 mg, 0.049 mmol) was added thereto, and the mixture was refluxed and stirred at a temperature of 200° C. for 48 hours. After the reaction was completed, the temperature was lowered to room temperature, water was added, and the resulting solid was filtered. The resulting solid was purified by column chromatography using dimethyl chloride and n-hexane to obtain ICZ-1-1 (66.4 mg, 28%).

II. Final product synthesis example

1. Example of synthesis of CP 5

1) Synthesis of sub 1-1

2,5-dibromo-1,3-difluorobenzene (2.0 g, 7.40 mmol), 4-(tert-butyl)phenol (3.2 g, 22.08 mmol), N-methylpyrrolidone of K ₂ CO ₃ (3.0 g, 22.08 mmol) (9 mL) The suspension was stirred under nitrogen atmosphere at 170 ^° C for 20 hours. The reaction mixture was diluted with toluene, poured into water and extracted. The organic layer was washed with water, dried over MgSO ₄ , filtered with silica gel, and concentrated. The residue was diluted with ethanol and filtered to give sub 1-1' (3.1 g, 80%).

Sub 1-1' (1.6 g, 3.00 mmol) was slowly added n-BuLi (1.6M, 2.0 mL, 3.30 mmol) at 0 ^° C to m-xylene (16 mL) solution. After 20 minutes, the mixture was stirred at room temperature for 1 hour. BBr ₃ (0.34 mL, 3.60 mmol) at 0 ^o C was added slowly. After 20 minutes, the mixture was stirred at room temperature for 30 minutes and at 40 ^o C for 30 minutes. I-Pr ₂ NEt (1.0 mL, 6.00 mmol) was slowly added at 0 ^o C, 30 minutes later, stirred at room temperature for 30 minutes, and stirred at 120 ^o C for 17 hours and cooled to room temperature. The reaction mixture was filtered with Forisil and concentrated. The residue was purified by column chromatography to give sub 1-1 (200.2 mg, 15%).

2) Synthesis of CP 5

ICZ-1-1 (150.0 mg, 0.31 mmol), sub 1-1 (157.0 mg, 0.34 mmol) and a mixture of toluene (4.5 mL) of t-BuONa (59.6 mg, 0.62 mmol) with argon and temperature of 70 Stirred back to stir. After 10 minutes, Pd ₂ (dba) ₃ (5.7 mg, 0.0062 mmol) and t-Bu ₃ P/HBF ₄ (7.2 mg, 0.0248 mmol) were added and stirred at 110°C overnight. Cooled to room temperature, diluted with CH ₂ Cl ₂ and filtered through silica gel. Recrystallization from Hexane/CH ₂ Cl ₂ gave compound CP 5 (93.8 mg, 35%).

2. Example of synthesis of CP 1

ICZ-1-1 (135.1 mg, 0.28 mmol), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (130.0 mg, 0.33 mmol) and t-BuONa (53.8 mg, 0.56 The mixture of mmol) toluene (4.5 mL) was replaced with argon, and the temperature was raised to 70 degrees and stirred. After 10 minutes, Pd ₂ (dba) ₃ (5.1 mg, 0.0056 mmol) and t-Bu ₃ P/HBF ₄ (6.5 mg, 0.0224 mmol) were added and stirred at 115°C overnight. Cooled to room temperature, filtered, washed with water and toluene. The obtained solid was purified by a silica gel column and recrystallized from Hexane/toluene to obtain compound CP 1 (141.9 mg, 64%).

3. Synthesis Example of CP 19

ICZ-1-1 (150.0 mg, 0.31 mmol), 2-(4-bromophenyl)-5-phenyl-1,3,4-oxadiazole (110.0 mg, 0.37 mmol) and t-BuONa (59.6 mg, 0.62 mmol) The mixture of toluene (4.5 mL) was replaced with argon and the temperature was raised to 70 degrees and stirred. After 10 minutes, Pd ₂ (dba) ₃ (5.7 mg, 0.0062 mmol) and t-Bu ₃ P/HBF ₄ (7.2 mg, 0.0248 mmol) were added and stirred at 110°C overnight. Cooled to room temperature, filtered, washed with water and toluene. The obtained solid was purified by silica gel column and recrystallized from Hexane/toluene to obtain compound CP 19 (152.9 mg, 70%).

Among the compounds of CP 1 to CP 26, the remaining compounds that do not describe a specific synthesis example can be synthesized by a method similar to the above synthesis method.

The synthesis example is for some exemplary compounds of the compounds represented by Formula 1, the reaction is BuchwaldHartwig cross coupling reaction, Suzuki cross-coupling reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095.), Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504) and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005 , 70, 5014.), Grignard reaction and Cyclic Dehydration reaction. Those skilled in the art will readily understand that the reaction proceeds even if other substituents defined in Chemical Formula 1 are combined in addition to the substituents specified in the specific synthetic examples.

Evaluation of material properties

The concentrations of 10 ^-4 M in the toluene solvent of the compound CP 5 of the present invention (Example 1), the compound CP 1 of the present invention (Example 2), and the comparative compound 1 (Comparative Example 1) and the comparative compound 2 (Comparative Example 2), respectively, Melt with and measure the photoluminescence (photoluminescence) are shown in Table 1 below. The UV-Vis absorption spectrum was measured using a Jasco V-750 Spectrophotometer, and the PL spectrum was measured using a Jasco FP-8500 Spectrofluorometer. The absorption peak was observed from the UV-Vis absorption spectrum, and the PL spectrum was confirmed by setting this value to the excitation wavelength during PL measurement.

Comparative Compound 1 Comparative Compound 2

As shown in Table 1, Example 1 exhibited a deep blue wavelength of 446 nm based on a peak, and showed a superiority as a TADF (delayed fluorescence) material with a blue characteristic compared to a conventional TADF (delayed fluorescence) material with a half width of 47 nm. . In the case of Example 2, due to the strong acceptor property of triazine, the color shifted to red, showing a light blue wavelength of 478 nm. The half-width is rather large at 86 nm, but it shows superiority as a sky blue TADF (delayed fluorescence) material. Materials used as a comparative example also showed a luminescence peak similar to the previous example. Comparative Example 1 was 449 nm, Comparative Example 2 was 482 nm, showing a difference of about 3-4 nm from the Example.

In order to confirm the TADF (delayed fluorescence) characteristics, a thin film was prepared by doping each of the preceding four substances in a DBFPO host by 20%, and the characteristics of the delayed fluorescence of the thin film were respectively PLQY (photoluminescence quantum yield) and TRPL ( Time exciton lifetime was measured by time resolved photoluminescence), and the results are shown in Table 1 and FIGS. 3 and 4 below. PLQY measured absolute PLQY using the integrating sphere embedded in Jasco FP-8500, and TRPL was measured using Hamamatsu C11367 Fluorescence Lifetime Spectrometer. Based on the PL peak measured above, the number of photons emitted was measured and compared until 10,000.

As shown in Table 1 and 3, in the case of Example 1 and Example 2, the total PLQY was measured to be very high, 95% and 91%, respectively, and Φ _p and Φ _d were measured to be 0.48 and 0.47, respectively. , Example 2 was measured to be 0.27 and 0.64, respectively. In addition, it was confirmed that the delayed component was increased due to the effect of small ΔE _ST , effectively causing reverse intersystem crossing (RISC), and the delayed exciton lifetime was short, as 4.27 μs and 2.19 μs, respectively.

However, in the case of Comparative Example 1, the delayed exciton lifetime was 76.7 ns very short, as the delayed fluorescence characteristic was hardly exhibited. This indicates that quenching is more prevalent than RISC. Total PLQY also decreased to 71%, Φ _p and Φ _d Φ _d was too low to measure the fluorescent moiety delayed by 0.60 and 0.11, respectively. Therefore, it was confirmed that the usability as a delayed fluorescent material was greatly reduced. In the case of Comparative Example 2, the total PLQY was measured to be high at 85%, but due to the molecular structure, the steric hindrance of the donor and acceptor was relatively small, resulting in a large ΔE _ST and delayed exciton lifetime (delayed). exciton lifetime) was significantly longer at 6.82 μs.

From the above results, it was confirmed that both of Example 1 and Example 2 of the present invention are excellent materials for use as a blue TADF (delayed fluorescence) material.

Device evaluation: Example 3

The ITO glass substrate is cut into 50 mm x 50 mm x 0.5 mm size, and then ultrasonically cleaned for 5 minutes using acetone, isopropyl alcohol and pure water, irradiated with ultraviolet rays for 30 minutes, exposed to ozone for cleaning, and then vacuumed. An ITO glass substrate was installed.

HATCN (7 nm) / TAPC (50 nm) / DCDPA (10 nm) / DBFPO (host) and the compound of the present invention CP 5 (dopant) 20 wt% (25 nm) / DBFPO (5 nm) / TPBi (20 nm) / LiF (1.5 nm) / Al (100 nm) were stacked in order to prepare an organic light emitting device.

In the case of forming the light emitting layer, organic light emission was performed in the same manner as in Example #3, except that Example 4 (Compound CP 1) and Comparative Examples 3 (Comparative Compound 1) and 4 (Comparative Compound 4) were used instead of Example 3. The device was fabricated.

Comparative Compound 1 Comparative Compound 2

Device characteristic evaluation

The driving voltage, luminance and efficiency at the current density of 10 mA/cm ² of the organic light-emitting devices manufactured in Examples 3 and 4 and Comparative Examples 3 and 4 were measured using the following method, and the results are shown in Tables 2 and 5 Shown.

-　 Luminance: Power was supplied from a current-voltmeter (Kethley SMU 236) and measured using a luminance meter PR650.

-　 Efficiency and emission spectrum: Power was supplied from a current-voltmeter (Kethley SMU 236) and measured using a luminance meter PR650.

	Driving voltage (V)	Max. Luminance (cd/m 2 )	Max. efficiency(%)	Efficiency@1000cd/m 2 (%)	λ emission	Emitting color (x,y)
Example 3	4.6	11,690	26.2	21.3	463	(0.14, 0.16)
Example 4	3.9	57,384	25.9	23.1	498	(0.22,0.49)
Comparative Example 3	5.5	6,810	8.1	6.7	473	(0.14,0.20)
Comparative Example 4	4.0	21,240	23.8	15.3	508	(0.25,0.53)

Simulation measurement: Difference in delayed fluorescent characteristics according to the position of the substituent

The simulation used Schrodinger's Maestro Materials Science 3.1.012, Release 2018-3 program.

The function used for the calculation was calculated by TDDFT (Time-dependent density functional theory) / B3LYP (Becke, three-parameter, Lee-Yang-Parr), basis set value 6-31G**.

The figure below shows the HOMO and LUMO calculation results of the inventive compound CP 1 and comparative compound 3.

Comparative compound 3

HOMO and LUMO simulation results of the compound CP 1 of the present invention are shown in FIG. 7.

HOMO and LUMO simulation results of Comparative Compound 3 are shown in FIG. 8.

It was confirmed that both of the compounds of the present invention, CP 1 and Comparative Compound 3, are well separated from HOMO and LUMO, which are properties found in delayed fluorescent materials. However, proper charge transfer (CT) in the molecule and high oscillator strength (vibration strength at a specific temperature of the molecule) are required.

In order for this characteristic to appear, HOMO and LUMO must be partially overlapped, and only CP 1, the present invention material, shows overlap in the orbital between the donor and the acceptor, and it can be confirmed that it has higher oscillator strength as shown in FIG. 6. have.

Finally, the triplet energy (T1) value of the compound CP 1 and the comparative compound 3 of the present invention are similarly shown, but it was confirmed that the ΔE _ST value generated a large difference.

-CP 1: T1 (2.576 eV), △E _ST (0.02 eV)

-Comparative compound 3: T1 (2.559 eV), △E _ST (0.144 eV)

In view of the above, it can be determined that the compound CP 1 of the present invention is a delayed fluorescent material than the comparative compound 3, and is far superior in performance and suitable.

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains will be capable of various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention, but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments.

The scope of protection of the present invention should be interpreted by the claims below, and all technologies within the scope equivalent thereto should be interpreted as being included in the scope of the present invention.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims priority in accordance with U.S. Patent Act 119(a) (35 USC § 119(a)) to Korean Patent Application No. 10-2018-0167093 filed in Korea on December 21, 2018. All contents are incorporated into this patent application by reference. In addition, if this patent application claims priority for the same reasons as above for countries other than the United States, all of the contents are incorporated into this patent application as a reference.

Claims (7)

1. Compound represented by the formula (1):

   <Formula 1>

   

   In Chemical Formula 1,

   1) R ₁ to R ₁₈ are each hydrogen, deuterium, halogen, C ₆ ~C ₆₀ aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And C ₆ ~ C _{30 It} is selected from an aryloxy group, R ₁ to R ₁₈ may be bonded to each other to form a ring,

   2) Ar ₁ and Ar ₂ are C ₆ to C ₆₀ aryl groups, respectively; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; A substituent represented by the following formula (2); A substituent represented by the following formula (3); And it is selected from the substituent represented by the following formula (4),

   <Formula 2>

   

   <Formula 3>

   

   <Formula 4>

   

   In Formulas 2 to 4,

   3) Y is O or N-Ar ₆ ,

   4) Ar ₃ to Ar ₆ are each C ₆ ~ C ₆₀ aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring `fused ring group,

   5) R ₁₉ to R ₂₆ are hydrogen, deuterium, halogen, cyano group, nitro group, C ₆ to C ₆₀ aryl group, respectively; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And C ₆ ~ C _{30 It} is selected from an aryloxy group, R ₁₉ to R ₂₆ may be bonded to each other to form a ring,

   6) At least one of Ar ₁ and Ar ₂ is represented by any one of Formula 2 to Formula 4,

   7) In R ₁ to R ₂₆ and Ar ₁ to Ar ₆ , the aliphatic hydrocarbon group, aryl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, deuterium, respectively ; Nitro group; Nitrile group; Halogen group; Amino group; A silane group unsubstituted or substituted with an alkyl group of C ₁ to C ₂₀ or an aryl group of C ₆ to C ₂₀ ; Siloxane groups; C ₁ ~ C ₂₀ alkylthio; C ₁ ~ C ₂₀ Alkoxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ aryl alkenyl group may be further substituted with one or more substituents selected from the group consisting of, and also these substituents may combine with each other to form a ring.
2. According to claim 1,

   Any one of Ar ₁ and Ar ₂ is a compound selected from the substituents represented by Formulas 2 to 4.
3. According to claim 1,

   The compound represented by Formula 1 is any one of the following compounds:

   

   

   

   

   

   .
4. A first electrode; A second electrode; And an organic material layer positioned between the first electrode and the second electrode, wherein the organic electric device comprises:

   The organic material layer is an organic electrical device comprising the compound of any one of claims 1 to 3.
5. The method of claim 4,

   The organic material layer includes at least one layer of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer,

   At least one layer of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport auxiliary layer, the electron transport layer and the electron injection layer comprises at least one of the compounds of claims 1 to 3.
6. A display device comprising the organic electric device of claim 4; And

   And a control unit controlling the display device.
7. The method of claim 6,

   The organic electric element is an electronic device that is one of an organic electroluminescent element, an organic solar cell, an organic photoreceptor, an organic transistor and an element for monochromatic or white lighting.

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