KR20180097955A - Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof - Google Patents

Abstract

Disclosed are: a compound represented by chemical formula 1; an organic electronic element comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode; and an electronic device including the same, and by including the compound represented by the chemical formula 1 in the organic layer, the driving voltage of the organic electronic element 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 such an organic light emitting phenomenon usually includes an anode, a cathode, and an organic layer formed therebetween. In order to improve the efficiency and stability of the organic electronic device, the organic material layer may have a multi-layer structure formed of different materials. For example, the organic material layer may include 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.

In the case of a polycyclic ring compound containing a hetero atom, the difference in characteristics depending on the material structure is very large and is applied to various layers as a material of an organic electric device. In particular, since the number of rings and fused positions in a polycyclic ring compound and the band gap (HOMO, LUMO), electrical properties, chemical properties, physical properties, etc. differ depending on the kind and arrangement of heteroatoms, Research has been carried out to apply it to an organic material layer.

For example, U.S. Patent Application Publication No. 2008-0145708 discloses an embodiment in which a polycyclic ring compound is applied to a hole transport layer or a phosphorescent host of an organic electronic device, and Korean Patent Laid-Open Publication No. 10-2007-0012218 Discloses an embodiment in which a polycyclic ring compound is applied to an electron transport layer of an organic electronic device.

The development of organic electroluminescent devices for the kind, number, and position of heteroatoms of polycyclic ring compounds is continuing. In particular, development of a host material for a light emitting layer using a polycyclic ring compound is further demanded.

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

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 organic electronic 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 of the light emitting layer 150, and preferably as a host material of 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 >

In the above formula (1), each symbol is defined as follows.

A ring is naphthalene, X and Y are independently of each other N (-L-Ar ₁ ), O, S or C (R ') (R ").

n and m are each an integer of 0 or 1, provided that n + m is an integer of 1 or more.

R ₁ to R ₁₂ independently from each other are hydrogen; heavy hydrogen; halogen; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; Heterocyclic group of O, N, S, Se, C 2 -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₆ -C ₆₀ aromatic ring and a C ₃ -C ₆₀ aliphatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; A C ₆ -C ₃₀ aryloxy group; 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, it is preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₁₈ aryl group, specifically, phenyl, biphenyl, naphthalene, phenanthrene, triphenylene And the like. When R ₁ to R ₁₂ are heterocyclic groups, it is preferably a C ₂ -C ₃₀ heterocyclic group, more preferably a C ₂ -C ₁₂ heterocyclic group, specifically, triazine, carbazole, etc. .

The ring formed by bonding neighboring groups of R ₁ to R ₁₂ to each other may be an aromatic ring, a heterocyclic ring, etc., and is preferably a C ₆ -C ₃₀ aromatic ring or a C ₂ -C ₃₀ heterocyclic group have.

Ar ₁ is a C ₆ to C ₆₀ aryl group; A fluorenyl group; A fused ring group of a C ₂ to C ₆₀ heterocyclic group C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring containing at least one heteroatom selected from O, N, S, Si and P; 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 R _a and R _b may combine with each other to form a ring.

When Ar ₁ is an aryl group, it is preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₁₈ aryl group, specifically, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, .

When Ar ₁ is a heterocyclic group, preferably a C ₂ -C ₃₀ heterocyclic group, more preferably a C ₂ -C ₁₈ heterocyclic group, specifically imidazole, pyridine, pyrimidine, triazine, benzoimide Benzothiazole, indole, benzothiophene, benzothiazole, benzothiazole, benzothiazole, benzothiazole, benzothiazole, benzothiazole, benzothiazole, benzothiazole, benzothiazole, Carbazole, 9,10-dihydro-9,9-dimethylacridine, thianthrene, benzothienopyrimidine, benzopuropyrimidine, naphthopyropyrimidine, naphthothienopyrimidine , Phenanthropuropyrimidine, pyrimidoindole, and the like.

In the case where Ar ₁ is a fluorenyl group, examples of the substituent include 9,9-dimethyl-9H-fluorene, 9,9'-spirobifluorene, 11,11-dimethyl-11H-benzofluorene, 9H- 7,7-dimethyl-7H-benzo [d] anthracene and the like when Ar ₁ is a fused ring group.

L and L 'are independently a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; Heterocyclic group of O, N, S, Se, C 2 -C 60 containing at least one heteroatom selected from the group consisting of Si and P; And a fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ .

When L and L 'are arylene groups, it is preferably a C ₆ -C ₃₀ arylene group, more preferably a C ₆ -C ₁₈ arylene group, specifically, phenyl, biphenyl, terphenyl, naphthalene, etc. have.

When L and L 'are a heterocyclic group, preferably a C ₂ -C ₃₀ heterocyclic group, more preferably a C ₂ -C ₁₈ heterocyclic group, specifically imidazole, pyridine, pyrimidine, triazine, Benzothiazole, benzothiazole, carbazole, benzoimidazole, quinazoline, benzoquinazoline, dibenzoquinazoline, quinoline, isoquinoline, benzothienopyrimidine, dibenzofuran, benzopuropyrimidine, Pyridopyrimidine, dibenzoquinoxaline, and the like can be given as examples of the compound of the present invention.

L and L 'are fluorenylene groups, 9,9-dimethyl-9H-fluorene, 9,9'-spirobifluorene, 11,11-dimethyl-11H-benzofluorene, 9H- And so on.

Wherein R ', R ", R _a and R _b are independently an aryl group of C ₆ -C ₆₀ with each other; fluorene group; at least one heteroatom selected from the group consisting of O, N, S, Se, Si , and P C ₂ -C ₆₀ heterocyclic group containing; C ₆ -C ₆₀ aromatic ring, and C ₃ -C ₆₀ aliphatic ring fused ring group of; selected from the group consisting of alkyl groups and C ₁ -C _50, and, R 'and R "may combine with each other to form a ring.

A ring formed by bonding neighboring groups of the A ring, R ₁ to R ₁₂ , Ar ₁ , L, L ', R', R ", R _a , R _b and R ₁ to R ₁₂ , Quot; R "are bonded to each other to form a ring formed by 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.

Preferably, the formula (1) may be represented by one of the following formulas (2) to (31).

      &Lt; Formula 2 > < EMI ID =

      &Lt; Formula 5 > < EMI ID =

 &Lt; Formula 8 > < EMI ID =

   &Lt; Formula 11 > < EMI ID =

 &Lt; Formula 14 > < EMI ID =

    &Lt; Formula 17 > < EMI ID = 18.0 >

  &Lt; Formula 20 > < EMI ID =

   &Lt; Formula 23 > < EMI ID =

  &Lt; Formula 26 >

  &Lt; Formula 29 > < EMI ID =

Wherein R ¹ to R ¹² , X, Y, L, Ar ', R' and R "are the same as defined in Formula 1, and R ₁₃ , R ₁₄ and R ₁₅ are independently of each other hydrogen, heavy hydrogen; halogen; C ₆ ~ C aryl group of _60; fluorene group; O, N, S, Si and P, at least one of C ₂ ~ containing a hetero atom C ₆₀ heterocyclic group of; C ₁ ~ alkyl group of C _50; C ₆ ~ C ₆₀ of the ring with C ₃ ~ C a fused ring of an aliphatic ring group of _60; a C ₂ ~ C ₂₀ alkenyl group; an alkoxy group of C ₁ ~ C _30; and C ₆ ~ C An aryloxy group having 1 to ₃₀ carbon atoms, and neighboring groups may be bonded to each other to form a ring.

Each of R ₁₃ , R ₁₄ and R ₁₅ is independently selected from the group consisting of 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.

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

Another embodiment of the present invention is a liquid crystal display comprising: a first electrode; A second electrode; And an organic layer formed between the first electrode and the second electrode and containing the compound represented by the formula (1) or formed in the formula (1). At this time, the compound represented by the general formula (1) may be contained in at least one layer of the hole injection layer, the hole transport layer, the light emission assisting layer, the light emitting layer, the electron transport assisting layer, the electron transport layer and the electron injection layer of the organic material layer. May be contained as a component of two or more kinds of mixtures. That is, the compound represented by the general formula (1) can be used as a material for the hole injecting layer, the hole transporting layer, the light emitting auxiliary layer, the light emitting layer, the electron transporting auxiliary layer, the electron transporting layer or the electron injecting layer. Preferably, the compound represented by the formula (1) can be used as the material of the light emitting layer, more preferably as the phosphorescent host material of the light emitting layer.

Another embodiment of the present invention may further include a light efficiency improvement layer formed on at least one side of the one side of the first electrode opposite to the organic material layer or one side of the one side of the second electrode opposite to the organic material layer Thereby providing an organic electric device.

Yet another embodiment of the present invention provides an electronic device including a display device including the organic electronic device and a control unit for driving the display device.

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

Synthetic example

[ Synthetic example  1] X is N-L- Ar _One Work  Occation

The compound represented by formula (1) according to the present invention can be prepared by the reaction path of the following reaction formula (1), but is not limited thereto.

<Reaction Scheme 1>

Core Synthetic example

The compound belonging to the core of the above reaction scheme 1 can be synthesized by the following reaction scheme 2, but is not limited thereto.

<Reaction Scheme 2>

inter-0 Synthetic example

The compound belonging to inter-O in Scheme 1 may be synthesized by the following reaction scheme 3, but is not limited thereto.

<Reaction Scheme 3>

The starting material in a round bottom flask was charged 1-chloro-2-iodobenzene ( 50 g, 209.7 mmol) and 2-chloroaniline (29.4 g, 29.4 mmol), Pd 2 (dba) 3 (T-Bu) ₃ (2.5 g, 12.6 mmol) in toluene (700 ml) was added to a solution of (t-Bu) ONa (60.5 g, 629.1 mmol) Lt; / RTI &gt; Upon completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. The concentrate was purified by silicagel column and recrystallized to obtain Inter-0 39.4 g (yield: 79%).

Core 6 Synthetic example

Examples of the synthesis of compounds belonging to Core 6 in Reaction Scheme 2 are as shown in Reaction Schemes 4 to 7 below, but are not limited thereto.

(1) Inter-7 Synthetic example

<Reaction Scheme 4>

1,7-dibromonaphthalene (CAS Registry Number: 58258-65-4) (30 g, 104.9 mmol) was added to the round bottom flask and dissolved in THF (350 ml), followed by addition of 2-nitrophenyl boronicacid : 5570-19-4) (19.3 g, 115.4 mmol), Pd (PPh 3) 4 (3.6 g, 3.1 mmol), K 2 CO 3 (43.5 g, 314.7 mmol was added) and water (180ml) and 90 ℃ Lt; / RTI &gt; After completion of the reaction, 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 17.2 g of product Inter-7 (yield: 50%).

(2) Inter-8 Synthetic example

<Reaction Scheme 5>

Inter-7 (15 g, 45.7 mmol), Inter-O (12 g, 50.3 mmol), Pd ₂ (dba) ₃ P (t-Bu) ₃ (0.6 g, 2.7 mmol) was added to the reaction mixture at room temperature, followed by the addition of triethylamine (1.3 g, 1.4 mmol) and (t- Bu) ONa (13.2 g, 137.1 mmol) Lt; / RTI &gt; 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 Inter-8 13.5 g (yield: 61%).

(3) Inter-9 Synthetic example

<Reaction Scheme 6>

Inter-8 To a round bottom flask (5 g, 10.3 mmol), (NHC) Pd (allyl) Cl (0.1 g, 0.2 mmol), K 2 CO 3 (2.8 g, 20.6 mmol) were dissolved in N, N-dimethylacetamide (35 ml), followed by stirring at 130 ° 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 g of Inter-9 (yield: 70%).

(4) Core 6's Synthetic example

<Reaction Scheme 7>

A round bottom flask was charged with Inter-9 (10 g, 24.2 mmol), PPh ₃ (19.1 g, 72.7 mmol), which was stirred at 180 ° C. After completion of the reaction, 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 7.4 g of Core 6 (yield: 80%).

Core 1 to Core 5 in Reaction Scheme 2 can also be prepared as described above. Examples of compounds belonging to Core 1 to Core 6 are as follows, and their FD-MS values are shown in Table 1.

[Table 1]

Example of synthesis of Sub

Examples of the synthesis of a compound belonging to Sub of Reaction Scheme 1 are as follows, but the present invention is not limited thereto.

Sub 21's Synthetic example

<Reaction Scheme 8>

2,4-dibromopyrimidine (CAS Registry Number: 3921-01-5) (24.46 g, 102.82 mmol) was added to a round bottom flask and dissolved in 360 ml of THF. Then, 4,4,5,5-tetramethyl- 2- (naphthalen-1-yl- d7) -1,3,2-dioxaborolane (CAS Registry Number: 1280709-91-2) (29.54 g, 113.11 mmol), Pd (PPh 3) 4 (4.75 g, 4.11 mmol), K ₂ CO ₃ (42.63 g, 308.47 mmol) and water (180 ml) were added and stirred at 90 ° C. After completion of the reaction, 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 18.03 g of the product (yield: 60%).

Sub 57's Synthetic example

<Reaction Scheme 9>

1,3-dibromobenzene (CAS Registry Number: 108-36-1) (10.07 g, 42.69 mmol) was added to a round bottom flask and 2,4-diphenyl-6- (4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2- yl) (CAS Registry -1,3,5-triazine Number: 1345345-08-5) (16.87 g, 46.95 mmol), Pd (PPh 3) 4 12.93 g (Yield: 78%) of the product was obtained using the Sub 21 synthesis method after adding 1.97 g (1.71 mmol) of K ₂ CO ₃ (17.70 g, 128.06 mmol), THF (150 ml) .

Sub 63's Synthetic example

<Reaction formula 10>

2,4-dichlorobenzo [4,5] thieno [3,2- d ] pyrimidine (CAS Registry Number: 160199-05-3) (21.85 g, 85.65 mmol) was added to a round bottom flask, (CAS Registry Number: 947770-80-1) (27.71 g, 94.21 mmol), Pd ((dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane PPh ₃ ) ₄ 14.25 g (Yield: 43%) of the product was obtained by using the Sub 21 synthesis method after addition of water (3.96 g, 3.43 mmol), K ₂ CO ₃ (35.51 g, 256.94 mmol), THF (300 ml) .

Sub 69's Synthetic example

<Reaction Scheme 11>

2,4-dichlorobenzo [4,5] thieno [2,3-d] pyrimidine (CAS Registry Number: 76872-40-7) (24.89 g, 97.56 mmol) was added to the round bottom flask, (CAS Registry Number: 1263272-83-8) (35.44 g, 107.32 mmol), Pd (PPh (2-hydroxyphenyl) -1,3,5-dioxaborolane ₃ ) ₄ 19.81 g (Yield: 48%) of the product was obtained using the Sub 21 synthesis method after the addition of the compound (4.51 g, 3.90 mmol), K ₂ CO ₃ (40.45 g, 292.69 mmol), THF (170 ml) .

Sub 90's Synthetic example

(1) Sub I-90 Synthetic example

<Reaction Scheme 12-1>

1-amino-2-naphthoic acid (CAS Registry Number: 4919-43-1) (75.11 g, 401.25 mmol) and urea (CAS Registry Number: 57-13-6) (168.69 g, 2808.75 mmol) were added together and stirred at 160 ° C. After the reaction was confirmed by TLC, the reaction mixture was cooled to 100 ° C, water (200 ml) was added, and the mixture was stirred for 1 hour. After completion of the reaction, the resulting solid was filtered under reduced pressure, washed with water, and then dried to obtain 63.86 g (yield: 75%) of the product.

(2) Sub II-90 Synthetic example

<Reaction Scheme 12-2>

N , N- Diisopropylethylamine (97.23 g, 752.36 mmol) was slowly added dropwise to the round bottom flask, and Sub I-90 (63.86 g, 300.94 mmol) obtained in the above synthesis was dissolved in POCl ₃ (200 ml) Lt; 0 &gt; C. After completion of the reaction, the reaction mixture was concentrated, and then ice water (500 ml) was added thereto, followed by stirring at room temperature for 1 hour. The resulting solid was filtered under reduced pressure and dried to obtain 67.47 g (yield: 90%) of the product.

(3) Sub 90 Synthetic example

<Reaction Scheme 12-3>

Sub II-90 (67.47 g, 270.86 mmol) obtained in the above synthesis was added to a round bottom flask and 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (CAS Registry Number: 24388-23 -6) (60.80 g, 297.94 mmol ), Pd (PPh 3) 4 (Yield: 57%) of the product was obtained using the Sub 21 synthesis method, by adding K ₂ CO ₃ (112.30 g, 812.57 mmol), THF (950 ml) and water (475 ml) .

Sub compound example

The compounds belonging to Sub may be, but not limited to, the FD-MS values of these compounds are shown in Table 2.

[Table 2]

Example of final compound synthesis

The final product of Scheme 1 may be synthesized as shown in Scheme 13, but is not limited thereto.

<Reaction Scheme 13>

After adding Core (1 equivalent), Sub (1.1 equivalent), Pd ₂ (dba) ₃ (0.03 eq) and (t-Bu) ONa (3 eq) into a round bottom flask and dissolving in toluene -Bu) ₃ (0.06 eq.) Was added and stirred at 120 &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 subjected to silicagel column and recrystallization to obtain a final product.

The final compound Synthetic example  One

<Reaction Scheme 14>

To a round bottom flask was added Core 6 (5 g, 13.1 mmol), Sub 9 (3.9 g, 14.5 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol) ) Was added and dissolved in toluene (45 ml). P (t-Bu) ₃ (0.2 g, 0.8 mmol) was added and stirred at 120 ° 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 2.0 g of final product (yield: 63%).

The final compound Synthetic example  2

<Reaction Scheme 15>

To a round bottom flask was added Core 5 (5 g, 13.1 mmol), Sub 10 (5.6 g, 14.5 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol) (T-Bu) ₃ (0.2 g, 0.8 mmol) was added thereto, followed by stirring at 120 ° C. Using the synthesis method of Scheme 13, 6.3 g (70%) of the desired compound was obtained.

The final compound Synthetic example  3

<Reaction Scheme 16>

(4 g, 14.5 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol) and (t-Bu) ONa (3.8 g, 39.4 mmol) were added to a round bottom flask, Was dissolved in toluene (45 ml), P (t-Bu) ₃ (0.2 g, 0.8 mmol) was added, and the mixture was stirred at 120 ° C. Using the synthesis method of Scheme 13, 6.3 g (77%) of the desired compound was obtained.

The final compound Synthetic example  4

<Reaction Scheme 17>

(3.5 g, 14.5 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol), (t-Bu) ONa (3.8 g, 39.4 mmol) in a round bottom flask, (T-Bu) ₃ (0.2 g, 0.8 mmol) was added thereto, followed by stirring at 120 ° C. Using the synthesis method of Scheme 13, 5.9 g (77%) of the desired compound was obtained.

The final compound Synthetic example  5

<Reaction Scheme 18>

To a round bottom flask was added Core 2 (5 g, 13.1 mmol), Sub 44 (5.6 g, 14.5 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol) (T-Bu) ₃ (0.2 g, 0.8 mmol) was added thereto, followed by stirring at 120 ° C. Using the synthesis method of Scheme 13, 7.2 g (80%) of the desired compound was obtained.

The final compound Synthetic example  6

<Reaction Scheme 19>

To a round bottom flask was added Core 6 (5 g, 13.1 mmol), Sub 63 (3.9 g, 14.5 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol) (T-Bu) ₃ (0.2 g, 0.8 mmol) was added thereto, followed by stirring at 120 ° C. Using the synthesis method of Scheme 13, 7.8 g (81%) of the desired compound was obtained.

[ Synthetic example  2] When X is S, O or C (R ') (R ")

When X is S, O or C (R ') (R ") in the general formula (1), the final compound can be synthesized by the following reaction scheme, but is not limited thereto.

<Reaction Scheme 20> When X is S

Synthesis of Core 7

(1) Synthesis of Core 7-a

1,7-Dibromonaphthalene (42 g, 146.87 mmol), (2-nitrophenyl) boronic acid (24.52 g, 146.87 mmol), Pd (PPh 3) 4 (5.09 g, 4.41 mmol), K 2 CO 3 (60.90 g, 440.61 mmol), THF (500 ml) and H ₂ O (200 ml) were used to synthesize Core 1-a to give 23.6 g (49%) of the product.

(2) Synthesis of Core 7-b

Dichlorobenzene (o-DCB) (200 ml) was reacted with 17.67 g (89%) of Core 7-a (22 g, 64.04 mmol), triphenylphosphine (43.96 g, 167.60 mmol) ).

(3) Synthesis of Core 7-c

(15.0 g, 45.58 mmol), Cu powder (0.32 g, 5.06 mmol), K ₂ CO ₃ (21.00 g, 151.94 mmol), 18-crown (15.0 g, 50.65 mmol) -6 (2.68 g, 10.13 mmol) and nitrobenzene (200 ml) were subjected to the synthesis of Core 1-c to obtain 10.6 g (42%) of the product.

(4) Synthesis of Core 7-d

Pd (OAc) ₂ (0.24 g, 1.05 mmol), P (t-Bu) ₃ (0.61 g, 2.11 mmol), K ₂ CO ₃ (8.74 g, 63.23 mmol) ) And DMA (100 ml) were obtained 5.7 g (73%) of the product using the above Core 1 synthesis method.

(5) Synthesis of Core 7-e

(8.85 g, 31.60 mmol), PdCl ₂ (dppf) ₂ (0.99 g, 1.22 mmol), KOAc (7.16 g, 72.92 mmol), DMF 100 ml), and the mixture is refluxed at 120 ° C for 6 hours. When the reaction is complete, cool the reaction mixture to room temperature, extract with MC, and wipe with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 7.8 g (77%) of the product.

(6) Synthesis of Core 7-f

Core 7-e (9.0 g, 21.57 mmol), (5-bromo-2-iodophenyl) (methyl) sulfane (8.51 g, 25.88 mmol), Pd (PPh 3) 4 (0.75 g, 0.65 mmol), K 2 CO ₃ (8.94 g, 64.70 mmol), THF (100 ml) and H ₂ O (40 ml) were obtained 6.8 g (64%) of the product using the above Core 1-a synthesis method.

(7) Synthesis of Core 7-g

Hydrogen peroxide (0.86 g, 25.15 mmol) and acetic acid (50 ml) were added to Core 7-f (7.2 g, 16.77 mmol) and stirred at room temperature for 3 hours. After the reaction was completed, NaOH aqueous solution was added to neutralize and then filtered to obtain 6.8 g (80%) of the product.

(8) Synthesis of Core 7-h

Add sulfuric acid (10 mL) to Core 7-g (6.0 g, 11.80 mmol) and stir at room temperature for 5 hours. After the reaction was completed, the reaction solution was neutralized with an aqueous NaOH solution and filtered to obtain 3.5 g (62%) of the product.

(9) Synthesis of Core 7

PdCl ₂ (dppf) ₂ (0.34 g, 0.42 mmol), KOAc (2.47 g, 25.19 mmol), DMF (3.0 g), and diboron bis (pinacolato) 80 ml) was obtained 3.2 g (73%) of the product using the above-described synthesis of Core 7-e.

&Lt; Reaction Formula 21 > When X is O

Core 8 Synthetic example

(1) Synthesis of Core 8-a

Core 7-e (13 g, 31.15 mmol) in 2,4-dibromophenol (9.42 g, 37.38 mmol), Pd (PPh 3) 4 (1.08 g, 0.93 mmol), K 2 CO 3 (12.92 g, 93.45 mmol) , 7.9 g (55%) of the product was obtained by using the above Core 1-a synthesis method, THF (150 ml), EtOH (80 ml) and H ₂ O (80 ml).

(2) Synthesis of Core 8-b

3-nitropyridine (0.09 g, 0.76 mmol), BzOOtBu (tert-butyl peroxybenzoate) (5.88 g, 30.28 mmol), Pd (OAc) ₂ (0.17 g, 0.76 mmol) , C ₆ F ₆ (hexafluorobenzene) (100 ml) and DMI (N, N'-dimethylimidazolidinone) (70 ml) were added and refluxed at 90 ° C. for 3 hours. When the reaction is complete, the reaction temperature is cooled to room temperature, extracted with EA, and wiped with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 2.7 g (39%) of the product.

(3) Synthesis of Core 8

(1.74 g, 4.23 mmol), PdCl ₂ (dppf) ₂ (0.20 g, 0.24 mmol), KOAc (1.41 g, 14.34 mmol), DMF 50 ml) was subjected to the synthesis of Core 7-e to obtain 1.7 g (71%) of the product.

When X is CR'R &quot;

Core 9 Synthetic example

(1) Synthesis of Core 9-a

Core 7-e (11 g, 26.36 mmol) to methyl 5-bromo-2-iodobenzoate (8.99 g, 26.36 mmol), Pd (PPh 3) 4 (0.91 g, 0.79 mmol), K 2 CO 3 (10.93 g, 79.08 mmol), THF (150 ml) and H ₂ O (70 ml) were used to obtain 9.1 g (68%) of the product using the above Core 1-a synthesis method.

(2) Synthesis of Core 9-b

Core 9-a (9 g, 17.84 mmol) and THF (200 ml) were added. 1.6 M methylmagnesium bromide (1.34 ml) was added at 0 ° C and the mixture was stirred at room temperature for 24 hours. When the reaction is complete, add 1 N HCl and stir for 10 minutes, then extract with EA and wipe with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 6.4 g (71%) of the product.

(3) Synthesis of Core 9-c

After dissolving Core 9-b (8 g, 15.86 mmol) in THF (200 ml), add 5 ml of methanesulfonic acid slowly at 0 ° C and stir at room temperature for 1 hour. After the reaction is completed, add sodium carbonate aqueous solution (100 ml), stir for 10 minutes, extract with MC and wipe with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 6.1 g (79%) of the product.

(4) Synthesis of Core 9

PdCl ₂ (dppf) ₂ (0.32 g, 0.39 mmol), KOAc (2.30 g, 23.44 mmol), DMF (2.85 g, 50 ml) was subjected to the synthesis of Core 7-e to obtain 3.6 g (86%) of the product.

The final compound Synthetic example

P-118 Synthetic example

Core 8 (2.9g, 5.73 mmol) , Sub 108 (2.21 g, 6.88 mmol), Pd (PPh 3) 4 (0.20 g, 0.17 mmol), K 2 CO 3 (2.38 g, 17.20 mmol), THF (80 ml ) And H ₂ O (20 ml) were obtained 2.3 g (65%) of the product using the synthesis of Core 1-a.

P-120 Synthetic example

Core 7 '(2.3g, 4.43 mmol ), Sub 1-50 (1.19g, 4.43 mmol), Pd (PPh 3) 4 (0.15 g, 0.13 mmol), K 2 CO 3 (1.80 g, 13.01 mmol), THF (60 ml) and H ₂ O (20 ml) were used to obtain 1.98 g (71%) of the product using the above Core 1-a synthesis method.

P-123 Synthetic example

Core 9 '(3.58g, 5.44 mmol ), Sub 109 (1.43g, 5.44 mmol), Pd (PPh 3) 4 (0.19 g, 0.16 mmol), K 2 CO 3 (2.25 g, 16.32 mmol), THF (70 ml) and H ₂ O (25 ml) were used to obtain 2.72 g (70%) of the product using the synthesis of Core 1-a.

The FD-MS values of the compounds P-1 to P-123 of the present invention prepared in the same manner as in the synthesis of the final compound are shown in Table 3 below.

 [Table 3]

Evaluation of manufacturing of organic electric device

[ Example  One] Red  Organic electroluminescent device

4,4 ', 4 "-Tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter referred to as" 2-TNATA ") was vacuum deposited on the ITO layer (anode) Layer.

Thereafter, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter referred to as "NPB") was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer, (1-phenylisoquinoline) iridium (III) acetylacetonate (hereinafter referred to as "(piq) ₂ Ir (acac)") was used as a dopant material on the hole transport layer, 95: 5 weight ratio to form a light emitting layer having a thickness of 30 nm.

Next, a hole blocking layer was formed by vacuum deposition of (1,1'-biphenyl-4-olato) bis (2-methyl-8-quinolinolato) aluminu Tris- (8-hydroxyquinoline) aluminum (hereinafter referred to as "Alq ₃ ") was deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.

Subsequently, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.

[ Example  2] to [ Example  19] Red organic electroluminescent device

An organic electroluminescence 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-9 of the present invention as a host material of the light emitting layer.

[ Comparative Example  1] to [ Comparative Example  3]

An organic electroluminescent device was prepared in the same manner as in Example 1 except that one of the following Comparative Compounds A to C was used in place of the compound P-9 of the present invention as a host material in the light emitting layer.

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

Electruminescence (EL) characteristics were measured with a photoresearch PR-650 by applying a forward bias DC voltage to the organic EL devices manufactured in Examples 1 to 42 and Comparative Examples 1 to 3 of the present invention And the T95 lifetime was measured by a life measuring apparatus manufactured by Mac Science Inc. at a reference brightness 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 compound of the present invention as a phosphorescent host material has significantly improved driving voltage, luminescent efficiency and lifetime as compared with an organic electroluminescent device using a comparative compound.

Comparative Example 1 used CBP (Comparative Compound A) used as a common host material as a host material, Comparative Example 2 and Comparative Example 3 used Comparative Compound B having indolocarbazole as a main skeleton, The comparative compound C was used as a host material. The device characteristics of Comparative Example 2 and Comparative Example 3 were superior to those of Comparative Example 1, and the device had an indolocarbazole skeleton as in Comparative Examples 2 and 3, When the compound of the present invention in which a carbazole other than indole is condensed is used as a host material, the efficiency, lifetime and driving voltage are further improved.

When a carbazole which is not an indole in the indolecarbazole is condensed like the compound of the present invention, since the phenyl is further condensed in the core, the physical properties of the compound such as the HOMO level and the T ₁ level are different from those of the comparative compounds 2 and 3 do. This change in physical properties allows the compounds of the present invention to have properties more consistent with the red host material as compared to the comparative compounds 2 and 3. Therefore, this fact suggests that changes in the physical properties of the compound during compound deposition for device fabrication will act as a major factor in device performance (such as energy balance), which may result in different device characteristics.

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 are 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 equivalents should be construed as falling within 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 (14)

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

In Formula 1,
A ring is naphthalene,
X and Y are independently N (-L-Ar ₁ ), O, S or C (R ') (R "), n and m are each an integer of 0 or 1, Integer,
R ₁ to R ₁₂ independently from each other are hydrogen; heavy hydrogen; halogen; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; Heterocyclic group of O, N, S, Se, C 2 -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₆ -C ₆₀ aromatic ring and a C ₃ -C ₆₀ aliphatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; A C ₆ -C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); adjacent groups may be bonded to each other to form a ring,
Ar ₁ is a C ₆ to C ₆₀ aryl group; A fluorenyl group; A fused ring group of a C ₂ to C ₆₀ heterocyclic group C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring containing at least one heteroatom selected from O, N, S, Si and P; 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 );
L and L 'are independently a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; Heterocyclic group of O, N, S, Se, C 2 -C 60 containing at least one heteroatom selected from the group consisting of Si and P; And a fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ ,
Wherein R ', R ", R _a and R _b are independently an aryl group of C ₆ -C ₆₀ with each other; fluorene group; at least one heteroatom selected from the group consisting of O, N, S, Se, Si , and P C ₂ -C ₆₀ heterocyclic group containing; C ₆ -C ₆₀ aromatic ring, and C ₃ -C ₆₀ aliphatic ring fused ring group of; selected from the group consisting of alkyl groups and C ₁ -C _50, and, R 'and R "may combine with each other to form a ring, and R _a and R _b may be bonded to each other to form a ring,
A ring formed by bonding neighboring groups of the A ring, R ₁ to R ₁₂ , Ar ₁ , L, L ', R', R ", R _a , R _b and R ₁ to R ₁₂ , Quot; R "are bonded to each other to form a ring formed by 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 &apos; -N (R ' _a ) (R &apos; _b ); And a combination of these. The method according to claim 1,
Wherein the compound of Formula 1 is one of the following Formulas 2 to 7:
&Lt; Formula 2 >< EMI ID =

&Lt; Formula 5 &gt;&lt; EMI ID =

In the general formulas (2) to (7), the definitions of R ¹ to R ¹² , X and Y are the same as defined in claim 1,
R ₁₃ , R ₁₄ and R ₁₅ 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 C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; And an aryloxy group having ₆ to ₃₀ carbon atoms, and neighboring groups may be bonded to each other to form a ring,
R ₁₃ , R ₁₄ and R ₁₅ are each 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 &apos; -N (R &apos; _a ) (R &apos; _b ); And a combination of these. The method according to claim 1,
Wherein the compound of formula (1) is one of the following formulas (8) to (13):
&Lt; Formula 8 >< EMI ID =

&Lt; Formula 11 &gt;&lt; EMI ID =

In the above formulas (8) to (13), the definitions of R ¹ to R ¹² , L and Ar ₁ are the same as those defined in claim 1,
R ₁₃ , R ₁₄ and R ₁₅ 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 C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; And an aryloxy group having ₆ to ₃₀ carbon atoms, and neighboring groups may be bonded to each other to form a ring,
R ₁₃ , R ₁₄ and R ₁₅ are each 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 &apos; -N (R &apos; _a ) (R &apos; _b ); And a combination of these. The method according to claim 1,
Wherein the compound of formula (1) is one of the following formulas (14) to (19):
&Lt; Formula 14 >< EMI ID =

&Lt; Formula 17 &gt;&lt; EMI ID = 18.0 &gt;

In the above Chemical Formulas 14 to 19, the definitions of R ¹ to R ¹² are the same as those defined in Claim 1,
R ₁₃ , R ₁₄ and R ₁₅ 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 C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; And an aryloxy group having ₆ to ₃₀ carbon atoms, and neighboring groups may be bonded to each other to form a ring,
R ₁₃ , R ₁₄ and R ₁₅ are each 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 &apos; -N (R &apos; _a ) (R &apos; _b ); And a combination of these. The method according to claim 1,
The compound of formula (1) is one of the following formulas (20) to (25):
&Lt; Formula 20 >< EMI ID =

&Lt; Formula 23 &gt;&lt; EMI ID =

In the above Chemical Formulas 20 to 25, the definitions of R ¹ to R ¹² are the same as those defined in Claim 1,
R ₁₃ , R ₁₄ and R ₁₅ 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 C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; And an aryloxy group having ₆ to ₃₀ carbon atoms, and neighboring groups may be bonded to each other to form a ring,
R ₁₃ , R ₁₄ and R ₁₅ are each 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 &apos; -N (R &apos; _a ) (R &apos; _b ); And a combination of these. The method according to claim 1,
The compound of formula 1 is one of the following formulas 26 to 31:
&Lt; Formula 26 >

&Lt; Formula 29 >< EMI ID =

In the above Chemical Formulas 26 to 31, R ¹ to R ¹² , R 'and R "are the same as defined in claim 1,
R ₁₃ , R ₁₄ and R ₁₅ 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 C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; And an aryloxy group having ₆ to ₃₀ carbon atoms, and neighboring groups may be bonded to each other to form a ring,
R ₁₃ , R ₁₄ and R ₁₅ are each 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 &apos; -N (R &apos; _a ) (R &apos; _b ); And a combination of these. 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 electroluminescent device according to any one of claims 1 to 7, wherein the organic layer comprises the compound of any one of claims 1 to 7. 9. The method of claim 8,
The compound is contained in at least one layer of the hole injection layer, the hole transport layer, the light emission assisting layer, the light emitting layer, the electron transport assisting layer, the electron transport layer and the electron injection layer of the organic material layer, Organic electroluminescent device. 10. The method of claim 9,
Wherein the compound is contained in the light emitting layer. 9. The method of claim 8,
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. 9. The method of claim 8,
Further comprising a light-efficiency-improvement layer formed on at least one side of the one surface of the first electrode and the second electrode opposite to the organic material layer. A display device including the organic electroluminescent device of claim 8; And
And a control unit for driving the display device. 14. The method of claim 13,
Wherein the organic electroluminescent device is one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor and a monochromatic illumination device.

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