KR20190007792A - Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof - Google Patents

Abstract

Disclosed is an organic electronic device comprising a compound represented by Chemical Formula (1) and a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, and an electronic device including the organic compound. The driving voltage of the organic electronic device can be lowered, and the luminous efficiency and lifetime can be improved.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound for an organic electronic device, an organic electronic device using the compound, and an electronic device using the compound.

TECHNICAL FIELD The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device therefor.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is often formed of a multilayer structure composed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

A material used as an organic material layer in an organic electric device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight, and may be classified into a phosphorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the light emitting efficiency through the light emitting layer. When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

Currently, the portable display market is growing in size as a large-area display, which requires more power than the power consumption required by existing portable displays. Therefore, power consumption becomes a very important factor for portable displays, which have a limited power source, such as a battery, and efficiency and lifetime issues must be solved.

The efficiency, lifetime, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases. As the driving voltage decreases, the crystallization of the organic material due to Joule heating, which occurs during driving, And the lifetime tends to increase. However, simply improving the organic material layer can not maximize the efficiency. This is because, when the optimum combination of the energy level and the T ₁ value between the respective organic layers, and the intrinsic properties (mobility, interface characteristics, etc.) of the materials are achieved, long life and high efficiency can be achieved at the same time. Therefore, it is necessary to develop a light emitting material having high thermal stability and achieving a charge balance in the light emitting layer efficiently.

That is, in order to sufficiently exhibit the excellent characteristics of the organic electronic device, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, the development of stable and efficient organic material layer materials for organic electroluminescent devices has not been sufficiently developed yet. Therefore, development of new materials is continuously required, and development of a host material for a light emitting layer is urgently required.

An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency, color purity and lifetime of the device, an organic electric device using the same, and an electronic device therefor.

In one aspect, the invention provides compounds represented by the formula:

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

By using the compound according to the embodiment of the present invention, not only the driving voltage of the device can be lowered, but also the luminous efficiency, color purity and lifetime of the device can be greatly improved.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is an illustration of an organic electroluminescent device according to the present invention. FIG.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

It should be noted that, in adding reference numerals to the constituent elements of the drawings, the same constituent elements are denoted by the same reference symbols as possible even if they are shown in different drawings. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In describing the components of the present invention, the terms first, second, A, B, (a), (b), and the like can be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements. 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, It should be understood that an element may be "connected," "coupled," or "connected."

In addition, when an element such as a layer, film, region, plate, or the like is referred to as being "on" or "on" another element, And the like. On the contrary, when an element is referred to as being " directly on " another element, it should be understood that it does not have another element in the middle.

As used in this specification and the appended claims, unless stated otherwise, the following terms have the following meanings:

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

As used herein, the term " alkyl " or " alkyl group " refers to a straight or branched Quot; means a radical of a saturated aliphatic group, including an alkyl group, a cycloalkyl-substituted alkyl group.

The term " haloalkyl group " or " halogenalkyl group " as used in the present invention means an alkyl group substituted with halogen unless otherwise stated.

The term " alkenyl group " or " alkynyl group ", as used herein, unless otherwise indicated, each have a double bond or triple bond of from 2 to 60 carbon atoms and include straight chain or branched chain groups, It is not.

The term " cycloalkyl " as used herein, unless otherwise specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.

The term " alkoxyl group ", " alkoxy group ", or " alkyloxy group " used in the present invention means an alkyl group to which an oxygen radical is attached and, unless otherwise stated, has a carbon number of 1 to 60, It is not.

As used herein, the term " aryloxyl group " or " aryloxy group " refers to an aryl group attached to an oxygen radical and, unless otherwise stated, has a carbon number of 6 to 60, but is not limited thereto.

The term " fluorenyl group " or " fluorenylene group " used in the present invention means a monovalent or divalent functional group in which R, R 'and R & Substituted fluorenyl group "or" substituted fluorenylene group "means that at least one of the substituents R, R 'and R" is a substituent other than hydrogen, and R and R' Together with a spy compound.

The terms " aryl group " and " arylene group ", as used herein, unless otherwise specified, each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, the aryl group or the arylene group includes a single ring, a ring group, a plurality of ring systems bonded together, a spiro compound and the like.

The term " heterocyclic group " as used herein includes not only aromatic rings such as " heteroaryl group " or " heteroarylene group ", but also nonaromatic rings, Means a ring of 2 to 60 rings, but is not limited thereto. The term " heteroatom ", as used herein, unless otherwise indicated, refers to N, O, S, P, or Si, wherein the heterocyclic group includes single ring, ring, And the like.

The " heterocyclic group " may also include a ring containing SO ₂ in place of the carbon forming the ring. For example, the "heterocyclic group" includes the following compounds.

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

As used herein, the term " polycyclic " includes ring assemblies such as biphenyl, terphenyl, and the like, as well as various fused ring systems and spiro compounds, including aromatic as well as non- The ring includes, of course, a heterocycle containing at least one heteroatom.

As used herein, the term " ring assemblies " means that two or more ring systems (a single ring or a fused ring system) are directly connected to each other through a single bond or a double bond, Means that the number of linkages is one less than the total number of rings in the compound. The ring assemblies may be directly connected to each other through a single bond or a double bond.

As used herein, the term " conjugated ring system " refers to a fused ring form shared by at least two atoms, in which the ring system of two or more hydrocarbons is conjugated and contains at least one heteroatom And at least one hetero ring system bonded thereto. Such conjugated ring systems may be aromatic rings, heteroaromatic rings, aliphatic rings or a combination of these rings.

The term " spiro compound " used in the present invention has a 'spiro union', and a spiro connection means a connection in which two rings share only one atom. At this time, atoms shared in two rings are called 'spyro atoms', and they are referred to as 'monospyros,' 'di spyroses,' and 'tri-spyros', depending on the number of spyro atoms contained in a compound. 'Compounds.

Also, if prefixes are named consecutively, it means that the substituents are listed in the order listed first. Means, for example, an alkoxy group substituted with an aryl group in the case of an arylalkoxy group, a carbonyl group substituted with an alkoxy group in the case of an alkoxycarbonyl group, and an alkenyl group substituted with an arylcarbonyl group in the case of an arylcarbonylalkenyl group, The arylcarbonyl group is a carbonyl group substituted with an aryl group.

In addition, a no explicit description, the terms used in this invention in the "unsubstituted or substituted", "substituted" is an alkyl group of deuterium, a halogen, an amino group, a nitrile group, a nitro _{group, C 1 -C 20, C 1} -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkyl amine group, C ₁ -C ₂₀ alkyl thiophene group, C ₆ -C ₂₀ aryl thiophene group, C ₂ -C ₂₀ alkenyl, C ₂ -C of 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 And a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, with the proviso that at least one substituent And is not limited to these substituents.

In the present specification, the 'group name' corresponding to the aryl group, the arylene group, the heterocyclic group and the like exemplified as the examples of the respective symbols and substituents thereof may be described as 'the name of the group reflecting the singer' You may. For example, in the case of phenanthrene, which is a kind of aryl group, a monovalent 'group' may be named 'phenanthryl' and a bivalent group may be named 'phenanthrylene' It may be described as "phenanthrene" which is the name of the parent compound. Similarly, in the case of pyrimidine, it may also be described as 'pyrimidine' irrespective of the valence number, or may be described as the 'name of the group' of the corresponding singer, such as pyrimidine di have.

Unless otherwise expressly stated, the formula used in the present invention is applied in the same manner as the definition of the substituent by the definition of the index of the following formula.

When a is an integer of 0, the substituent R ¹ is absent. That is, when a is 0, it means that all of the carbons forming the benzene ring are bonded to hydrogen. In this case, And the chemical formula or compound may be described. When a is an integer of 1, one substituent R < ¹ > is bonded to any one of carbon atoms forming a benzene ring, and when a is an integer of 2 or 3, for example, , R < ¹ > may be the same or different from each other when a is an integer of 2 or more.

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

1, an organic electroluminescent device 100 according to an embodiment of the present invention includes a first electrode 120, a second electrode 180 and a first electrode 120 formed on a substrate 110, And an organic material layer containing a compound according to the present invention is provided between the two electrodes 180. In this case, the first electrode 120 may be an anode and the second electrode 180 may be a cathode (cathode). In case of an inverting type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, and an electron injecting layer 170 sequentially on the first electrode 120. At this time, at least one of these layers may be omitted or may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transporting auxiliary layer, a buffer layer 141, It may also serve as a hole blocking layer.

Also, although not shown, the organic electroluminescent device according to an embodiment of the present invention further includes a protective layer or a light-efficiency-improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer can do.

The compound according to one embodiment of the present invention applied to the organic layer includes a hole injecting layer 130, a hole transporting layer 140, a light emitting auxiliary layer 151, an electron transporting auxiliary layer, an electron transporting layer 160, 170), a host or a dopant material of the light emitting layer 150, or a material of the light efficiency improving layer. For example, the compound of the present invention can be used as a material for the light emitting layer 150, the hole transporting layer 140, and / or the light emitting auxiliary layer 151, and can be preferably used as a host material for the light emitting layer 150.

On the other hand, even if the core is the same core, since the band gap, the electrical characteristics, the interface characteristics, and the like can be changed depending on which substituent is bonded at which position, the selection of the core and the combination of the sub- In particular, when the optimal combination of the energy level and T ₁ value between the organic layers, and the intrinsic properties (mobility, interface characteristics, etc.) of the materials are achieved, long life and high efficiency can be achieved at the same time.

Accordingly, in the present invention, by forming the light emitting layer 150 using the compound represented by Chemical Formula 1, the energy level and T ₁ value between each organic material layer, the intrinsic characteristics (mobility, interface characteristics, etc.) It is possible to simultaneously improve the life span and the efficiency.

An organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. For example, a metal or a metal oxide having conductivity or an alloy thereof may be deposited on a substrate to form a cathode 120, and a hole injection layer 130 may be formed thereon. A hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170, and then depositing a material that can be used as a cathode 180 on the organic layer. have. A light emitting auxiliary layer 151 may be further formed between the hole transporting layer 140 and the light emitting layer 150 and an electron transporting auxiliary layer may be further formed between the light emitting layer 150 and the electron transporting layer 160.

In addition, the organic material layer may be formed using a variety of polymer materials, not a vapor deposition method, or a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, It is possible to produce a smaller number of layers by a method such as a dipping process, a screen printing process, or a thermal transfer process. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.

The organic electroluminescent device according to an embodiment of the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of high resolution realization and fairness, and can be manufactured using existing color filter technology of LCD. Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented. Typically, a stacking method in which R (Red), G (Green) and B (Blue) light emitting parts are arranged side by side, and R, G and B light emitting layers are stacked up and down , And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light from the electroluminescent material. Can be applied to such WOLED.

The organic electroluminescent device according to an embodiment of the present invention may be one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, or a device for monochromatic or white illumination.

Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and a control unit for controlling the display device. The electronic device may be a current or future wired or wireless communication terminal and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

Hereinafter, the compound according to one aspect of the present invention will be described.

A compound according to one aspect of the present invention is represented by the following formula (1).

≪ Formula 1 >

Each symbol in the above formula (1) can be defined as follows.

R ¹ to R ¹² independently from each other are hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And -L'-N (R _a ) (R _b ); and neighboring groups may be bonded to each other to form a ring.

When R ¹ to R ¹² are aryl groups, they may preferably be C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₁₄ aryl groups, specifically, phenyl, biphenyl, naphthalene, phenanthrene and the like . When R ¹ to R ¹² are heterocyclic groups, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₂ heterocyclic group, specifically, a pyrimidine, triazine, carbazole, etc. have.

The rings formed by bonding adjacent groups of R ¹ to R ¹² to each other are C ₆ to C ₆₀ aromatic hydrocarbons, C ₂ to C ₆₀ heteroatoms containing at least one heteroatom of O, N, S, Si and P A ring, a fluorene, or the like, and specifically may be benzene, naphthalene, phenanthrene, and the like.

The X ring is a C ₆ to C ₆₀ aromatic hydrocarbon; Fluorene; _{O, N, S, C 2} ~ C ₆₀ heteroaryl rings containing Si and P, at least one of the hetero atoms in the; And a fused ring of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring.

When the X ring is an aromatic hydrocarbon, it is preferably a C ₆ -C ₃₀ aromatic hydrocarbon, more preferably a C ₆ -C ₁₈ aromatic hydrocarbon, specifically benzene, biphenyl, naphthalene, phenanthrene, triphenylene, , Fluoranthene, and the like. If the X ring is a hetero ring, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably C ₂ ~ C ₂₄ of the heterocycle, in particular pyridine, pyrimidine, pyrazine, pyridazine, quinoline, quinoxaline, quinazoline Benzothiophene, dibenzothiophene, benzonaphthothiophene, dibenzofuran, benzonaphthofuran, carbazole, benzothienopyrimidine, benzothiophene, benzothiophene, benzothiophene, Pyrimidopyrimidine, pyrimidoindole, 1,1-dimethyl-1H-indene, pyrimidodimethylindene, imidazopyridine, imidazoquinoline, dihydrodiphenylphenazine, dihydrodimethylphenylacridine , Phenyl phenoxazine, phenylphenothiazine, thianthrene, dibenzodioxine, naphthyridine, benzopyridothiophene, benzothienoquinoxaline, benzofuroquinoxaline, and the like. When X ring is fluorene, it may be 9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, or the like.

L 'is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And a C ₂ to C ₆₀ heterocyclic group.

R _a and R _b are each independently a C ₆ to C ₆₀ aryl group; A fluorenyl group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P;

An aryl group, an aryl group, an aromatic hydrocarbon, a fluorenyl group, a fluorenylene group, a fluorene, a heterocyclic group, a heterocyclic ring, a fused ring group, a fused ring, an alkyl group, an alkenyl group, an alkynyl group, , And rings formed by bonding adjacent groups of R ¹ to R ¹² to each other are respectively deuterium; halogen; A silane group substituted or unsubstituted with an alkyl group having _{1 to 20} carbon atoms or an aryl group having _{6 to 20} carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; Aryl alkenyl group of C ₈ -C _20; -L ' -N (R ' _a ) (R ' _b ); And combinations thereof, wherein L ', R _a and R _b are as defined above.

The formula (1) may be represented by the following formula (2).

(2)

Wherein R ¹ to R ¹² are as defined in Chemical Formula 1 and X ¹ to X ⁴ are each independently N, C (R '), N (R'), S, O, or C (R ' ) (R "), and m is 0 or 1.

Wherein R 'and R ", independently of each other hydrogen, heavy hydrogen; halogen; C ₁ -C ₂₀ alkyl group or a C ₆ aryl group a substituted or unsubstituted silane group of the -C _20; siloxane group; a boron group; germanium group; cyano group; a C ₂ -C ₂₀ alkynyl; a nitro group; C ₁ -C ₂₀ alkylthio Sy of; alkyl group of _{C 1 -C 20;; C 1} -C 20 alkoxy group of C ₂ -C ₂₀ alkenyl group of; an aryl group of C ₆ -C ₂₀ substituted with heavy hydrogen;; C ₆ -C ₂₀ aryl group, a fluorenyl group; O, N, S, C 2 containing at least one heteroatom selected from the group consisting of Si and P heterocyclic group of -C _20; C ₃ -C ₂₀ cycloalkyl _{group; -L'-N (R a)} (R b); C 7 -C 20 arylalkyl group; a C ₈ -C ₂₀ aryl alkenyl group; And combinations thereof, and neighboring R '' may be bonded to each other to form a ring.

When R _a and R _b are aryl groups, it is preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₁₄ aryl group, specifically, phenyl, biphenyl, naphthalene, phenanthrene and the like . When R _a and R _b are a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₂ heterocyclic group, specifically, dibenzofuran, dibenzothiophene, etc. have. When R _a and R _b are fluorenyl groups, they may be 9-dimethyl-9H-fluorene, 9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, and the like.

The formula (2) may be represented by the following formula (3) or (4).

 &Lt; Formula 3 > < Formula 4 >

In the above formulas (3) and (4), R ¹ to R ¹² and X ¹ to X ⁴ are as defined in formula (2).

The formula (1) may be represented by one of the following formulas (5) to (18).

&Lt; Formula 5 > < EMI ID = &Lt; Formula 7 &gt;

&Lt; Formula 8 > < EMI ID = &Lt; Formula 10 &gt;

  &Lt; Formula 11 > < EMI ID = &Lt; Formula 13 &gt;

 &Lt; Formula 14 > < EMI ID = &Lt; Formula 16 &gt;

   &Lt; Formula 17 > &Lt; Formula 18 >

In the above Chemical Formulas 5 to 18, R ¹ to R ¹² and X ¹ to X ⁴ are as defined in Chemical Formula 2.

X ⁵ to X ³³ is independently N, C (R '), N (R'), S, O or C (R ') (R " ) , and, Y ¹ and Y ² are independently N (R eachother ), S, O or C (R ') (R "), wherein R' is as defined in formula (2).

Specifically, Formula 1 may be one of the following compounds.

In another aspect of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode. At this time, the organic material layer includes the compound represented by the formula (1).

Wherein the organic compound layer includes at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer, and an electron injection layer, wherein the compound represented by Chemical Formula 1 is a hole injection layer, Emitting layer, the light-emitting auxiliary layer, the light-emitting layer, the electron transporting auxiliary layer, the electron transporting layer, and the electron injection layer, and may be included in the light emitting layer. At this time, the compound may be contained in the form of a single compound or a mixture of two or more compounds. Preferably, the compound represented by the formula (1) may be used as a host material of a light emitting layer, particularly a red phosphorescent host material.

Hereinafter, the synthesis examples of the compound represented by the formula (1) according to the present invention and the production examples of the organic electric device will be specifically described with reference to examples, but the present invention is not limited to the following examples.

Synthetic example

Illustratively, the compound represented by formula (1) according to the present invention can be prepared according to the following reaction scheme 1 or scheme 2, but is not limited thereto.

<Reaction Scheme 1>

<Reaction Scheme 2>

Synthesis of Sub 1

Sub 1 of Scheme 1 may be synthesized by the reaction path of Scheme 3 below, but is not limited thereto.

<Reaction Scheme 3>

Synthesis of Sub 1-1

(1) Synthesis of Sub 1-I

The starting material, 2,7-dibromonaphthalene (40.0 g, 139.9 mmol) then into the round bottom flask was dissolved in THF 700 mL, (2-nitrophenyl ) boronic acid (51.4 g, 307.7 mmol), Pd (PPh 3) 4 (4.9 g, 4.2 mmol), K ₂ CO ₃ (58.0 g, 419.6 mmol) and 300 mL of water were added and stirred at 80 ° C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 42.2 g (yield: 84%) of the product.

(2) Synthesis of Sub 1-1

Sub 1-I (42.2 g, 113.9 mmol) obtained in the above synthesis was placed in a round bottom flask and dissolved in 570 mL of DMF. Then, PPh ₃ (89.9 g, 341.8 mmol) was added and stirred at 165 &lt; 0 &gt; C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 25.5 g (yield: 73%) of the product.

Synthesis of Sub 1-7

(1) Synthesis of Sub 1-II-1

9-iodophenanthrene (30.0 g, 78.3 mmol) and 10-nitrophenanthren-9-yl boronic acid (23.01 g, 86.16 mmol) were reacted with 30.1 g (Yield: 80%).

(2) Synthesis of Sub 1-II

24.2 g (yield: 74%) of the product was obtained by using Sub 1-II-1 (30.0 g, 62.7 mmol) and (2-nitrophenyl) boronic acid (11.5 g, 69.0 mmol) .

(3) Synthesis of Sub 1-7

Sub-1-II (24.0 g, 46.1 mmol) was subjected to the synthesis of Sub 1-1 to obtain 15.6 g of the product (yield: 74%).

Synthesis of Sub 1-11

(1) Synthesis of Sub 1-III-1

Sub 1-1 (20.0 g, 65.3 mmol) was dissolved in 350 mL of DMF in a round bottom flask, and NBS (N-bromosuccinimide (12.8 g, 71.8 mmol) was added and stirred at room temperature for 6 hours. , Dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 19.8 g (yield: 79%) of the product

(2) Synthesis of Sub 1-11

17.5 g (Yield: 78%) of Sub 1-III-1 (18.0 g, 62.7 mmol) and phenanthren-3-ylboronic acid (11.4 g, 51.4 mmol) were obtained using the Sub 1-I synthesis method.

Synthesis of Sub 1-13

(1) Synthesis of Sub 1-IV-1

2-bromo-7-iodonaphthalene (30.0 g, 90.1 mmol) and 4-chloro-2-nitrophenyl boronic acid (20.0 g, 99.1 mmol) were reacted with 27.7 g (Yield: 85%).

(2) Synthesis of Sub 1-IV-2

22.2 g (Yield: 80%) of the product was obtained using Sub 1-IV-1 (25.0 g, 68.9 mmol) and 2-nitrophenyl boronic acid (12.7 g, 75.8 mmol) .

(3) Sub 1-IV-3 synthesis

10.1 g (yield: 60%) of Sub 1-IV-2 (20.0 g, 49.4 mmol) was obtained using the Sub 1-1 synthesis method.

(4) Sub 1-13 Synthesis

Sub-1-IV-3 (10.0 g, 29.3 mmol) and 9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazol- , 32.3 mmol) was subjected to the synthesis of Sub 1-I to obtain 15.5 g (yield: 75%) of the product

Examples of the compound included in Sub 1 include, but are not limited to, the following. Table 1 shows values of FD-MS (Field Desorption-Mass Spectrometry) for the compounds included in Sub 1 illustrated below.

[Table 1]

Sub 2 Synthetic example

The compound belonging to Sub 2 of Reaction Scheme 1 can be synthesized by the following reaction path, but is not limited thereto.

Synthetic Example of Sub 2-19

2-bromo-4-phenylquinazoline (23.5 g, 82.6 mmol) and Pd ₂ (dba) were added to a round bottom flask containing toluene (300 mL) ₃ (1.75 g, 1.9 mmol), P ( t- Bu) ₃ (0.8 g, 3.8 mmol) and NaO t- Bu (18.3 g, 190.6 mmol) were sequentially added and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 21.5 g (yield: 77%) of the product.

Synthetic example of Sub 2-39

22.2 g (Yield: 76%) of 2-bromo-3-phenylquinoxaline (27.9 g, 97.8 mmol) was obtained from 2,3- dichloro-1H- indole ).

Synthetic Example of Sub 2-50

11.9 g (Yield: 72%) of the product was obtained by the synthesis of sub 1-I using triphenylen-2-ylboronic acid (13.3 g, 48.7 mmol) and 4-bromo-1,2-dichlorobenzene (10.0 g, 44.3 mmol) .

Synthetic Example of Sub 2-66

bromobenzene (9.7 g, 61.7 mmol) and 3,4-dichloroaniline (5.0 g, 30.9 mmol) were obtained in a yield of 7.2 g (yield: 74%).

Examples of the compound included in Sub 2 include, but are not limited to, the following. Table 2 shows the values of FD-MS (Field Desorption-Mass Spectrometry) for the compounds included in Sub 2 exemplified below.

[Table 2]

Of the final compound Synthetic example

Example of P-3 synthesis

Sub 1-1 (4.6 g, 15.0 mmol) was added to a round bottom flask and dissolved in toluene (100 mL). Sub 2-3 [Cas. 2050-75-1] (3.0 g, 15.0 mmol ), Pd 2 (dba) 3 (0.4 g, 0.5 mmol), P (t -Bu) 3 (0.2 g, 0.9 mmol), NaO t -Bu (4.3 g , 45.0 mmol), which was stirred at 100 &lt; 0 &gt; C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 3.5 g (yield: 54%) of the product.

Example of P-19 synthesis

Sub-1-1 (5.5 g, 18.0 mmol) and Sub 2-19 (18.0 g, 7.9 mmol) were subjected to the synthesis of P-3 to obtain 7.2 g of the product (yield: 60%).

P-26 Synthetic examples

Sub 1-1 (4.8 g, 15.7 mmol) and Sub 2-26 [Cas. 2213-63-0] (3.1 g, 15.7 mmol) was obtained 3.9 g (yield: 58%) of the product using the above synthesis method of P-3.

Example of P-27 synthesis

Sub-1-1 (4.1 g, 13.4 mmol) and Sub 2-27 [Cas No. 26907-93-7] (3.3 g, 13.4 mmol) were reacted with 3.5 g (yield: 54%).

Example of P-39 synthesis

Sub-1-1 (4.6 g, 15.0 mmol) and Sub 2-39 (5.9 g, 15.0 mmol) were obtained in a yield of 6.5 g (yield: 69%) using the above synthesis method of P-3.

Example of P-46 synthesis

Sub 1-7 and (5.5 g, 12.0 mmol) and Sub 2-45 [Cas. 4926-53-8] (2.3 g, 12.0 mmol) was obtained as a crude product (4.2 g, yield 62%) using the above synthesis method of P-3.

Example of P-50 synthesis

Sub 1-11 (5.6 g, 11.6 mmol) and Sub 2-1 (Cas No. 2). 95-50-1] (1.7 g, 11.6 mmol) was obtained 4.2 g (Yield: 66%) of the product using the above synthesis method of P-3.

Example of P-52 synthesis

Sub 1-13 (4.9 g, 7.0 mmol) and Sub 2-1 (Cas No. 2). 95-50-1] (1.0 g, 7.0 mmol) was obtained 2.7 g (Yield: 50%) of the product using the above synthesis method of P-3.

Example of P-58 synthesis

Sub-1-1 (6.6 g, 21.5 mmol) and Sub 2-50 (8.0 g, 21.5 mmol) were subjected to the synthesis of P-3 to obtain 8.2 g of the product (yield: 63%).

Example of P-74 synthesis

Sub-1-1 (3.9 g, 12.7 mmol) and Sub 2-66 (4.0 g, 12.7 mmol) were subjected to the synthesis of P-3 to obtain 4.6 g of the product (yield: 66%).

P-83 Synthetic Example

Sub 1-1 (4.4 g, 14.4 mmol) and Sub 2-75 [Cas. 943611-33-4] (4.1 g, 14.4 mmol) was obtained 4.6 g (Yield: 62%) of the product using the above synthesis method of P-3.

Example of P-94 synthesis

Sub 1-1 (5.5 g, 18.0 mmol) and Sub 2-86 (Cas No. 2). 164471-02-7] (6.3 g, 18.0 mmol) was obtained 6.1 g (yield: 58%) of the product using the above synthesis method of P-3.

Table 3 below shows the values of FD-MS (Field Desorption-Mass Spectrometry) of the final compound synthesized according to Synthesis Example.

[Table 3]

Evaluation of manufacturing of organic electric device

[ Example  One] Red  Organic electroluminescent device (phosphorescent host)

A 4,4 ', 4 "-tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter abbreviated as" 2-TNATA ") film was vacuum deposited on the ITO layer (anode) After the formation of the injection layer, a 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as NPD) film was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Next, the compound P-1 of the present invention was used as a host material on the hole transport layer and bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate (hereinafter referred to as "(piq) ₂ Ir (acac) (1, 1'-biphenyl-4-olato) bis (2-methyl-8-quinolinolato) as a hole blocking layer was deposited on the light emitting layer to a thickness of 30 nm. ) aluminum (hereinafter abbreviated as " BAlq &quot;) was vacuum deposited to a thickness of 10 nm, and tris- (8-hydroxyquinoline) aluminum (hereinafter abbreviated as &quot; Alq ₃ &quot;) was deposited as an electron transport layer on the hole- Lt; RTI ID = 0.0 &gt; Then, an organic electroluminescence device was fabricated by depositing LiF, an alkali metal halide as an electron injection layer, to a thickness of 0.2 nm and then depositing Al to a thickness of 150 nm to form a cathode.

[ Example  2] to [ Example  34]

An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound P-1 of the present invention as a host material in the light emitting layer.

[ Comparative Example  1] and [ Comparative Example  2]

An organic electroluminescent device was prepared in the same manner as in Example 1, except that the following compound A or the compound B was used instead of the compound P-1 of the present invention as a host material in the light emitting layer.

&Lt; Comparative Compound A > < Comparative Compound B >

Electruminescence (EL) characteristics were measured with photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 1 to 34, Comparative Example 1 and Comparative Example 2 of the present invention And the T95 lifetime was measured using a life measuring apparatus manufactured by Mac Science Inc. at a luminance of 2500 cd / m ^2. The measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the results of Table 4, the organic electroluminescent device using the organic electroluminescent device material of the present invention as a phosphorescent host significantly improved the luminous efficiency, lifetime and driving voltage. That is, when the compound of the present invention is used as a host material, compared with Comparative Compound A, which is CBP mainly used as a host material, and Comparative Compound B, which is similar to the compound of Formula 1 of the present invention, as a host material, The luminous efficiency, lifetime and driving voltage were remarkably improved.

This is because the compound of the present invention having a novel structure compared to the comparative compounds has appropriate HOMO, LUMO energy, and the charge balance of holes and electrons in the luminescent layer is increased.

While the present invention has been described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention is not limited by these embodiments. The scope of protection of the present invention should be construed according to the following claims, and all the techniques within the scope of the same should be construed as being included in the scope of the present invention.

100: organic electric element 110: substrate
120: first electrode 130: hole injection layer
140: Hole transport layer 141: Buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode

Claims (11)

A compound represented by the following formula (1):
&Lt; Formula 1 >

In Formula 1,
R ¹ to R ¹² independently from each other are hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; And a C ₆ to C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); adjacent groups may be bonded to each other to form a ring,
The X ring is a C ₆ to C ₆₀ aromatic hydrocarbon; Fluorene; _{O, N, S, C 2} ~ C ₆₀ heteroaryl rings containing Si and P, at least one of the hetero atoms in the; And a fused ring of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring,
L 'is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And a C ₂ to C ₆₀ heterocyclic group,
R _a and R _b are each independently a C ₆ to C ₆₀ aryl group; A fluorenyl group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P;
An aryl group, an aryl group, an aromatic hydrocarbon, a fluorenyl group, a fluorenylene group, a fluorene, a heterocyclic group, a heterocyclic ring, a fused ring group, a fused ring, an alkyl group, an alkenyl group, an alkynyl group, , Rings formed by bonding adjacent groups of R ¹ to R ¹² to each other are respectively deuterium; halogen; A silane group substituted or unsubstituted with an alkyl group having _{1 to 20} carbon atoms or an aryl group having _{6 to 20} carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; Aryl alkenyl group of C ₈ -C _20; -L ' -N (R &apos; _a ) (R &apos; _b ); And a combination of these. The method according to claim 1,
(1) is represented by the following formula (2): < EMI ID =
(2)

Wherein R ¹ to R ¹² are the same as defined in claim 1,
X ¹ to X ⁴ are independently of each other N, C (R '), N (R'), S, O or C (R '
Wherein R 'and R ", independently of each other hydrogen, heavy hydrogen; halogen; C ₁ -C ₂₀ alkyl group or a C ₆ aryl group a substituted or unsubstituted silane group of the -C _20; siloxane group; a boron group; germanium group; cyano group; a C ₂ -C ₂₀ alkynyl; a nitro group; C ₁ -C ₂₀ alkylthio Sy of; alkyl group of _{C 1 -C 20;; C 1} -C 20 alkoxy group of C ₂ -C ₂₀ alkenyl group of; an aryl group of C ₆ -C ₂₀ substituted with heavy hydrogen;; C ₆ -C ₂₀ aryl group, a fluorenyl group; O, N, S, C 2 containing at least one heteroatom selected from the group consisting of Si and P heterocyclic group of -C _20; C ₃ -C ₂₀ cycloalkyl _{group; -L'-N (R a)} (R b); C 7 -C 20 arylalkyl group; a C ₈ -C ₂₀ aryl alkenyl group; And combinations thereof, and neighboring R '' may be bonded to each other to form a ring. The method according to claim 1,
(1) is represented by one of the following Chemical Formulas (3) to (18):
&Lt; Formula 3 >< Formula 4 >

&Lt; Formula 5 >< EMI ID =

&Lt; Formula 8 &gt;&lt; EMI ID =

&Lt; Formula 11 >< EMI ID =

&Lt; Formula 14 &gt;&lt; EMI ID =

&Lt; Formula 17 >< EMI ID =

In the above Chemical Formulas 3 to 18,
R ¹ to R ¹² are as defined in claim 1,
X ¹ to X ³³ independently of one another are N, C (R '), N (R'), S, O or C (R '
Y ¹ and Y ² are independently of each other N (R '), S, O or C (R') (R "),
Wherein R 'and R ", independently of each other hydrogen, heavy hydrogen; halogen; C ₁ -C ₂₀ alkyl group or a C ₆ aryl group a substituted or unsubstituted silane group of the -C _20; siloxane group; a boron group; germanium group; cyano group; a C ₂ -C ₂₀ alkynyl; a nitro group; C ₁ -C ₂₀ alkylthio Sy of; alkyl group of _{C 1 -C 20;; C 1} -C 20 alkoxy group of C ₂ -C ₂₀ alkenyl group of; an aryl group of C ₆ -C ₂₀ substituted with heavy hydrogen;; C ₆ -C ₂₀ aryl group, a fluorenyl group; O, N, S, C 2 containing at least one heteroatom selected from the group consisting of Si and P heterocyclic group of -C _20; C ₃ -C ₂₀ cycloalkyl _{group; -L'-N (R a)} (R b); C 7 -C 20 arylalkyl group; a C ₈ -C ₂₀ aryl alkenyl group; And combinations thereof, and neighboring R '' may be bonded to each other to form a ring,
Wherein L ', R _a and R _b are as defined in claim 1. The method according to claim 1,
Wherein the compound of formula (I) is one of the following compounds:

. A first electrode; A second electrode; And an organic material layer formed between the first electrode and the second electrode, the organic material layer containing a compound according to any one of claims 1 to 4. 6. The method of claim 5,
Wherein the compound is contained in the form of a single compound or a mixture of two or more compounds. 6. The method of claim 5,
Wherein the organic material layer includes at least one of a hole injection layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer, and an electron injecting layer. 8. The method of claim 7,
Wherein the compound is used as a red phosphorescent host material of the light emitting layer. 6. The method of claim 5,
Wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process. A display device comprising the organic electroluminescent device of claim 5; And
And a control unit for driving the display device. 11. The method of claim 10,
Wherein the organic electroluminescent device is one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, and a monochromatic or white illumination device.

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