KR20150137400A - Organic electronic element using a compound for organic electronic element, and an electronic device thereof - Google Patents

Abstract

Provided in the present invention is an organic electric element comprising a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, and including at least one light emitting layer. A dopant of the light emitting layer includes a compound represented by chemical formula 1, and a host of the light emitting layer includes at least one among compounds represented by chemical formula 2 to chemical formula 4. When the compound represented by chemical formula 1 is included in the dopant of the light emitting layer, and compounds represented by chemical formula 2 to chemical formula 4 are included in the host of the light emitting layer, driving voltage of the organic electric element is reduced, and light emitting efficiency, color purity, stability, and durability are improved.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent device using organic electroluminescent compound,

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device using an organic electroluminescent compound 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 the light emitting material in order to increase the light emitting efficiency through the light emitting layer. The principle is that when a small amount of dopant having a smaller energy band gap than a host forming the light emitting layer is mixed with the light emitting layer, the excitons generated in the light emitting layer are transported as a 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, light of a desired wavelength 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 and the intrinsic properties (mobility, interfacial 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, development of a stable and efficient organic material layer for an organic electric device has not yet been sufficiently developed. Particularly, development of a host material and a dopant material of the light emitting layer is urgently required.

An object of the present invention is to provide an organic electroluminescent device using a compound which can lower the driving voltage of the device and improve the luminous efficiency, color purity, stability and lifetime of the device, and an electronic device thereof.

In one aspect, the present invention provides an organic electronic device using the compound represented by the following formula and an electronic device therefor.

A first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer comprises a host and a light emitting layer including a dopant, wherein the dopant of the light emitting layer is a compound And the host of the light emitting layer comprises at least one of the compounds represented by the following general formulas (2) to (4).

    &Lt; Formula 1 > < EMI ID =

     &Lt; Formula 3 > < Formula 4 >

By using the compound according to an embodiment of the present invention, not only the driving voltage of the device can be lowered, but also the luminous efficiency, color purity, stability 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 numerals even though 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 "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 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, an aryl group or an arylene group means a single ring or a multicyclic aromatic group, and neighboring substituents include aromatic rings formed by bonding or participating in the reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirobifluorene group, or a spirobifluorene group.

The prefix "aryl" or "ar" means a radical substituted with an aryl group. For example, the arylalkyl group is an alkyl group substituted with an aryl group, the arylalkenyl group is an alkenyl group substituted with an aryl group, and the radical substituted with an aryl group has the carbon number described in the present specification.

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

The term "heteroaryl group" or "heteroarylene group" as used in the present invention means an aryl or arylene group having 2 to 60 carbon atoms each containing at least one heteroatom unless otherwise specified, And includes at least one of a single ring and a multi-ring, and neighboring functional devices may be formed in combination.

The term "heterocyclic group ", as used herein, unless otherwise specified, includes one or more heteroatoms, has from 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, Aromatic rings. Adjacent functional groups may be combined and formed.

As used herein, the term "heteroatom " refers to N, O, S, P or Si unless otherwise stated.

Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms and an "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise specified, the term "ring" as used herein refers to a fused ring consisting of an aliphatic ring of 3 to 60 carbon atoms or an aromatic ring of 6 to 60 carbon atoms or a heterocycle of 2 to 60 carbon atoms, or combinations thereof, Saturated or unsaturated ring.

Other hetero-compounds or hetero-radicals other than the above-mentioned hetero-compounds include, but are not limited to, one or more heteroatoms.

In addition, a no explicit description, the terms used in this invention in the "unsubstituted or substituted", "substituted" is heavy hydrogen, an alkyl group of a halogen group, an amino group, a nitrile group, a nitro _{group, C 1 -C 20, C 1} - alkyl group of C ₂₀ alkoxy group, C ₁ -C ₂₀ alkyl amine group, C ₁ -C ₂₀ of a thiophene group, a C ₆ -C ₂₀ aryl thiophene group, alkenyl group, C ₂ of the C ₂ -C ₂₀ - alkynyl, C ₃ -C ₂₀ cycloalkyl, C ₆ of the C ₆ -C ₂₀ aryl group, a C ₈ -C ₂₀ substituted with an aryl group, a heavy hydrogen of the aryl -C ₂₀ alkenyl group, a silane group of C _20, 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, and a substituted or unsubstituted aryl group, And is not limited to these substituents.

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, substituent R ¹ is absent. 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 each coupled as follows: and wherein R ¹ may be the same or different from each other, a is the case of 4 to 6 integer, and bonded to the carbon of the benzene ring in a similar way, while the display of the hydrogen bonded to the carbon to form a benzene ring Is omitted.

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 110 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, the remaining layers except the light emitting layer 150 may not be formed. An electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like, and the electron transport layer 160 may 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 material layer may be a host or a dopant of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, It may be used as a material for the light-efficiency improvement layer.

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.

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, an organic electroluminescent device according to one aspect of the present invention will be described.

In one embodiment of the present invention, the present invention provides an organic electroluminescent device comprising at least one of compounds represented by the following general formulas (1) to (4).

The organic electronic device includes a first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode. The organic material layer may include at least one of the compounds represented by Chemical Formulas 1 to 4 below.

The organic layer may include a host and a light-emitting layer including a dopant, and the light-emitting layer may include at least one of the compounds represented by Chemical Formulas 1 to 4 below.

The dopant of the light emitting layer may include a compound represented by the following Chemical Formula 1, and the host of the light emitting layer may include at least one compound represented by Chemical Formulas 2 to 4 below.

On the other hand, the compound contained in the organic material layer may consist of the same kind of compound, but it may be a mixture of two or more different kinds of compounds represented by the following general formulas (1) to (4)

For example, the dopant material of the light emitting layer according to an embodiment of the present invention may contain two different compounds, such as the following individual compounds 1-1 and 1-2, and the following individual compounds 1-1, 1-2, and 2 -1. &Lt; / RTI &gt;

In addition, the host material of the light emitting layer according to an embodiment of the present invention may contain two different compounds as shown in the following individual compounds 3-1 and 3-2, May contain two different compounds and may contain three or more different compounds, such as the following individual compounds 3-1, 3-2 and 3-3, and the following individual compounds 3-1, 4-1 and 5 -1. &Lt; / RTI &gt;

In another embodiment of the present invention, the present invention provides 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 The organic electroluminescent device further includes an organic electroluminescent device.

The compound included in the organic electro device according to one aspect of the present invention will now be described.

  &Lt; Formula 1 > < EMI ID =

In Formula 1, n is an integer of 0 to 4,

R ¹ to R ⁶ independently of one another are hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; And at least one heteroatom selected from the group consisting of O, N, S, Si and P A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; A C ₁ -C ₅₀ alkoxy group; An alkenyl group of C ₂ -C ₂₀ ; And -L ^a -N (R ^a ) (R ^b ); For example, R ¹ to R ⁶ independently of each other may be hydrogen, methyl, phenyl, and the like.

R ¹ to R ⁵ may be bonded to each other to form at least one ring. Specifically, R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ and / or R ⁴ , R ⁵ may combine with each other to form at least one ring. Here, R ¹ to R ⁵ which do not form a ring may be defined as defined above.

And R ^{6 may} also be bonded to each other to form at least one ring. When n is an integer of 2 or more, a plurality of R ^{6 s} may be the same or different, and a group in which some of adjacent groups may combine to form a ring and not form a remaining ring may be defined as defined above.

The rings formed by the adjacent groups include at least one heteroatom selected from the group consisting of C ₃ -C ₆₀ aliphatic rings, C ₆ -C ₆₀ aromatic rings, O, N, S, Si and P A fused ring consisting of a C ₂ -C ₆₀ hetero ring, or a combination thereof, and may be a single ring or multiple rings, as well as a saturated or unsaturated ring.

L ^a is a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And a C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P;

R ^a and R ^b are independently of each other a C ₆ -C ₆₀ aryl group; A fluorenyl group; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And a C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P;

In Formula 1, 1 is an integer of 0 to 2, and A may be represented by Formula 1-1 or Formula 1-2.

In Formula 1-1, and the P ring is N (nitrogen), a substituted or unsubstituted heterocyclic group of the unsubstituted C ₂ -C ₂₀ containing, can aryl date of the Q ring is a substituted or unsubstituted C ₆ -C _20. At this time, N (nitrogen) in the P ring forms a coordination bond with Ir (iridium), and C (carbon) in the Q ring forms a covalent bond with the Ir (iridium).

When the P ring and the Q ring are each substituted, i) each substituent is independently selected from the group consisting of deuterium; A halogen group; A C ₆ -C ₂₀ aryl group; A fluorenyl group; And at least one heteroatom selected from the group consisting of O, N, S, Si and P A C ₂ -C ₂₀ heterocyclic group; And C ₁ -C ₂₀ alkyl group; selected from the group consisting of or, ii) if the plurality each of the substituents form a ring between at least one neighboring group by combining to each other, or iii) unsubstituted substituents P and Q ring substituent Can be combined with each other to form a ring.

In Formula 1-2, one of two O (oxygen) may form a coordination bond with Ir (iridium), and the other may form a covalent bond with Ir (iridium).

In Formula 1-2, R ⁷ and R ⁸ independently represent hydrogen; heavy hydrogen; An aryl group of C ₆ -C ₆₀ ; And at least one heteroatom selected from the group consisting of O, N, S, Si and P A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; A C ₁ -C ₅₀ alkoxy group; And an alkenyl group of C ₂ -C ₂₀ .

    (2)

In Formula 2, a and b are each an integer of 0 or 1, and a + b may be 1 or more. When a and b are each 0, it means a single bond.

X and Y may be independently of each other S, O, N (R '), C (R') (R ") or Si (R ') (R").

Wherein R 'and R "are independently of each other, hydrogen, an aryl group of _{C 6 -C 60; O, N} , S, including at least one heteroatom selected from the group consisting of Si and P A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; And an alkenyl group having _{2 to 60} carbon atoms, and may be bonded to each other to form a ring.

Ar ¹ is a C ₆ -C ₆₀ aryl group; A fluorenyl group; And at least one heteroatom selected from the group consisting of O, N, S, Si and P A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; And -L ^a -N (R ^a ) (R ^b ); Here, L ^a , R ^a and R ^b may be respectively defined as defined above. For example, Ar ¹ can be phenyl, naphthyl, pyridine, pyrimidine, triazine, quinazoline, benzoimidazole, and the like.

L ¹ is a single bond; C ₆ -C ₆₀ arylene groups; A C ₂ -C ₆₀ heteroarylene group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; And And a divalent aliphatic hydrocarbon group. For example, L ¹ may be a single bond, phenyl, pyridine, pyrimidine, quinazoline, and the like.

m is an integer of 0 to 2, and o and q are each an integer of 0 to 4;

R ⁹ to R ¹¹ are, independently of each other, deuterium; An aryl group of C ₆ -C ₆₀ ; And at least one heteroatom selected from the group consisting of O, N, S, Si and P A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; A C ₁ -C ₅₀ alkoxy group; An alkenyl group of C ₂ -C ₂₀ ; And -L ^a -N (R ^a ) (R ^b ); Here, L ^a , R ^a and R ^b may be respectively defined as defined above. For example, R ⁹ to R ¹¹ may independently be carbazole, dibenzofuran, indole, and the like.

Further, R ⁹ to R ¹¹ may bond to each other to form at least one ring. Here, R ⁹ to R ¹¹ which do not form a ring may be defined as defined above. For example, when q and m are both 2, adjacent R ^{9 s} may combine with each other to form a ring, and R ¹⁰ may be an aryl group or a heterocyclic group independently of each other even when adjacent to each other.

Of course, when q is an integer of 2 or more, a plurality of R ^{9 s} may be the same or different, and a group in which some of the adjacent groups are bonded to each other to form a ring and not form a remaining ring is selected from the above-defined substituent group . The same applies when m and / or o is an integer of 2 or more.

On the other hand, rings formed by joining adjacent groups may be defined as defined above.

    (3)

In Formula 3,

Z ¹ to Z ¹⁶ independently of one another are C (R) or N, at least one of Z ⁵ to Z ⁸ and at least one of Z ⁹ to Z ¹² is C (R), wherein one of Z ⁵ to Z ⁸ and C of C (R) in one of Z ⁹ to Z ¹² may be bonded to L ² instead of binding to R.

When C (R) of Z ¹ to Z ¹⁶ is adjacent to each other, adjacent Rs may be bonded to each other to form a ring.

R is hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; And at least one heteroatom selected from the group consisting of O, N, S, Si and P A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; And -L ^a -N (R ^a ) (R ^b ); Here, L ^a , R ^a and R ^b may be respectively defined as defined above.

W may be N (Ar ³ ), S, O or C (R ') (R "), and R' and R" may each be defined as defined above.

Ar ² and Ar ³ are each independently a C ₆ -C ₆₀ aryl group; A fluorenyl group; And at least one heteroatom selected from the group consisting of O, N, S, Si and P A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; And an arylamine group of C ₆ -C ₆₀ . For example, Ar ² and Ar ³ can be, independently of each other, phenyl, biphenyl, pyrazole, pyridine, pyrimidine, triazine, quinazoline and the like.

L ² independently represent a single bond; C ₆ -C ₆₀ arylene groups; A C ₂ -C ₆₀ heteroarylene group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; And And a divalent aliphatic hydrocarbon group.

    &Lt; Formula 4 >

In Formula 4,

R ¹² to R ²³ independently from each other are hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; And at least one heteroatom selected from the group consisting of O, N, S, Si and P A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; A C ₁ -C ₅₀ alkoxy group; An alkenyl group of C ₂ -C ₂₀ ; And -L ^a -N (R ^a ) (R ^b ); Here, L ^a , R ^a and R ^b may be respectively defined as defined above. For example, R ¹² to R ²³ independently of each other may be hydrogen, phenyl, dibenzothiophene, and the like.

R ¹² to R ²³ may be bonded to each other to form at least one ring. Specifically, R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ , R ¹⁷ and R ¹⁸ , R ¹⁸ and R ¹⁹ , R ¹⁹ and R ²⁰ , R ²⁰ and R ²¹ , R ²¹ and R ²² , R ²² and R ²³ and / or R ²³ and R ¹² may combine with each other to form at least one ring. Here, R ¹² to R ²³ which do not form a ring may be defined as defined above. The rings formed by joining adjacent groups may be defined as defined above.

In the above Chemical Formulas 1 to 4, the fluorenyl group may include a spirobifluorenyl group and a spirobifluorenyl group.

The aryl group, the fluorenyl group, the heterocyclic group, the fused ring group, the aliphatic hydrocarbon group, the alkyl group, the alkenyl group, the alkoxyl group, the arylene group, and the fluorenylene group are each independently selected from the group consisting of deuterium; A halogen group; A silane group; 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; C ₆ -C ₂₀ An 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 ; And an arylalkenyl group having from _{8 to 20} carbon atoms.

In another embodiment of the present invention, the compound represented by Formula 1 may be represented by one of the following formulas.

       &Lt; Formula 5 > < EMI ID =

       &Lt; Formula 7 > < EMI ID =

       &Lt; Formula 9 > < EMI ID =

In the formulas (5) to (10), R ¹ to R ⁸ , 1 and n may be defined as defined in Formula (1).

In another embodiment of the present invention, the compound represented by Formula 1 may be one of the following compounds.

In another embodiment of the present invention, the compound represented by Formula 2 may be one of the following compounds.

In another embodiment of the present invention, the compound represented by Formula 3 may be one of the following compounds.

In another embodiment of the present invention, the compound represented by Formula 4 may be one of the following compounds.

In yet another embodiment of the present invention, there is provided a liquid crystal display comprising: a first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer includes a host and a light emitting layer including a dopant, wherein the dopant of the light emitting layer is a compound And a host of the light emitting layer comprises at least one of the compounds represented by Chemical Formulas 2 to 4; And a control unit for driving the display device.

Hereinafter, the synthesis examples of the compounds represented by the general formulas (1) to (4) contained in the organic electroluminescent device of the present invention and the production example of the organic electroluminescent device of the present invention will be specifically described. But is not limited to the examples.

Synthetic example

The above compound was carried out by the following method, but is not limited thereto.

I. Formula 1 Synthetic example

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

<Reaction Scheme 1> When l is 0

&Lt; Reaction Formula 2 > When l is 1 or 2

One. Sub  1 of Synthetic example

Sub 1 of Reaction Scheme 1 is prepared by the reaction path of Reaction Scheme 3 below, but is not limited thereto.

<Reaction Scheme 3>

Sub 1 (2) (1 eq.), Pd (PPh ₃ ) ₄ (0.05 eq.), 4-bromo-2-chloro-5-methylpyridine (1 eq.) Were dissolved in THF (4.4 mL / K ₂ CO ₃ (3 eq.), Water (2.2 mL / 1 mmol of starting material) and stirred at 80 &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, and the resulting compound was separated by silica gel column chromatography to obtain the product Sub 1 (3). Sub 1 (4) (1.1 eq.), Pd (PPh ₃ ) ₄ (0.05 eq.), And water (1 eq.) Were dissolved in THF (2.2 mL / 1 mmol of starting material) was added and stirred at 80 &lt; 0 &gt; 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 separated by silica gel column chromatography to obtain the product Sub 1.

Examples of Sub 1 include, but are not limited to, the following FD-MS values.

[Table 1-1]

2. Product  1 of Synthetic example

Ir (acac) ₃ (1 eq.) Was added to Sub 1 (4 eq.) And refluxed with glycerol under nitrogen for 18-24 hours. After the reaction was completed, the obtained solid substance was filtered, purified through column chromatography, and dried under a vacuum pump for 5 hours to obtain a final compound.

(1) Compound 1-4 Synthetic example

Ir (acac) ₃ (4.89 g, 10 mmol) was added to Sub 1-4 (10.37 g, 40 mmol) and refluxed with 350 mL of Glycerol under nitrogen for 18 hours. After the reaction was completed, the obtained solid substance was filtered, purified through column chromatography, and dried under vacuum pump for 5 hours to obtain 6.12 g (yield: 63%) of Compound 1-4.

(2) Compound 1-20 Synthetic example

Ir (acac) ₃ (4.89 g, 10 mmol) was added to Sub 1-20 (13.4 g, 40 mmol) and refluxed with 350 mL of glycerol under nitrogen for 24 hours. After the reaction was completed, the obtained solid substance was filtered, purified through column chromatography, and dried under a vacuum pump for 5 hours to obtain 7.25 g (yield: 58%) of Compound 1-20.

The FD-MS values of the compounds 1-1 to 1-25 prepared according to the above Synthesis Examples are shown in Table 1-2.

[Table 1-2]

3. Product  2 of Synthetic example

Product 2 of Scheme 2 is prepared by the reaction path of Scheme 4 but is not limited thereto.

<Reaction Scheme 4>

(1) Compound 2-26 Synthetic example

Pentane-2,4-dione (7 g, 70 mmol), Na ₂ CO ₃ (7.4 g, 70 mmol) and 100 mL of 2-ethoxy ethanol were placed in an Ir compound (10.0 g, 7 mmol) and reacted at 130 ° C. for 24 hours under nitrogen. After the reaction was completed, the obtained solid substance was filtered, purified by column chromatography, and dried under a vacuum pump for 3 hours to obtain 1.6 g (yield: 30%) of Compound 2-26.

4. Product  3 of Synthetic example

Product 3 of Scheme 2 is prepared by the reaction scheme of Scheme 5 or Scheme 6 but is not limited thereto.

<Reaction Scheme 5>

<Reaction Scheme 6>

(One) Sub  A Synthetic example

IrCl ₃ (1 eq.) Was added to 2-phenylpyridine (2.5 eq.) And the reaction was carried out at 140 ° C for 24 hours under a nitrogen atmosphere at a ratio of 2-ethoxy ethanol: H ₂ O 3: 1. When the reaction is complete, the resulting solid is extracted with CH ₂ Cl ₂ and water, the organic layer is dried over MgSO ₄ and passed through a 2 cm thick filter combined with silica gel and celite. The filtered liquid was concentrated, recrystallized and dried under a vacuum pump for 5 hours to obtain a product Sub A.

(2) Sub  B Synthetic example

Sub A (1 eq.) And Sub Aa (about 10 eq.) Were added to 2-ethoxy ethanol with Na ₂ CO ₃ (10 eq.) And reacted at 130 ° C for 24 hours. After completion of the reaction, the obtained solid material was filtered, purified through column chromatography, and dried under vacuum pump for 3 hours to obtain the product Sub B.

(3) Compound 2-1 Synthetic example

Sub-A (10.7 g, 10 mmol), Sub 1-1 (6.47 g, 25 mmol) and silver triflate (2.5 g, 10 mmol) were added to 2-ethoxy ethanol and reacted at 130 ° C for 24 hours under nitrogen. After the reaction was completed, the resulting solid substance was filtered, purified through column chromatography, and dried under a vacuum pump for 3 hours to obtain 3.1 g (yield: 36%) of the compound 2-1.

(4) Compound 2-15 Synthetic example

Sub-A (10.7 g, 10 mmol), Sub 1-15 (7.15 g, 25 mmol) and silver triflate (2.5 g, 10 mmol) were added to 2-ethoxy ethanol and reacted at 130 ° C for 24 hours under nitrogen. After the reaction was completed, the obtained solid substance was filtered, purified through column chromatography, and dried under a vacuum pump for 3 hours to obtain 3.0 g (yield: 38%) of Compound 2-15.

(5) Compound 2-19 Synthetic example

Sub 1-19 (5.0 g, 15 mmol), an ancillary ligand, was added to Sub B (5.99 g, 10 mmol) Ir, and a 120 W microwave was applied at 240 ° C. for 20 minutes with Glycerol. After the reaction was completed, the obtained solid substance was filtered, purified through column chromatography, and dried under vacuum pump for 3 hours to obtain 2.8 g (yield: 33%) of Compound 2-19.

(6) Compound 2-22 Synthetic example

Sub-1-22 (5.0 g, 15 mmol), an ancillary ligand, was added to Sub B (5.99 g, 10 mmol) Ir and a 120 W microwave was applied at 240 ° C. for 20 minutes with Glycerol. After the reaction was completed, the obtained solid substance was filtered, purified through column chromatography, and dried under a vacuum pump for 3 hours to obtain 2.7 g (yield: 32%) of the compound 2-22.

Meanwhile, FD-MS values of the compounds 2-1 to 2-25 prepared according to the above Synthesis Example are shown in Table 1-3.

[Table 1-3]

II . 2 Synthetic example

Illustrative examples of the compound 3-9 in the compound represented by the formula (2) according to the present invention are shown in the following reaction scheme (7), but the present invention is not limited thereto.

<Reaction Scheme 7>

(One) Sub  3-2 Synthetic example

Sub 3-1 (5.3 g, 20 mmol) was dissolved in anhydrous ether, the temperature of the reaction was lowered to -78 ° C, n-BuLi (2.5 M in hexane) (1.4 g, 22 mmol) was slowly added dropwise, Stir for 30 min. The temperature of the reaction was then lowered to -78 ° C and triisopropyl borate (5.6 g, 30 mmol) was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 3.2 g (yield: 71%) of Sub 3-2.

(2) Sub  3-3 Synthetic example

Sub 3-2 (3.2g, 14.2mmol) and 1-iodo-2-nitrobenzene ( 3.5g, 14.2mmol), Pd (PPh 3) 4 (0.5g, 0.4mmol), K 2 CO 3 (5.9 g, 42.6 mmol) was dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated. The resulting product was separated by column chromatography to obtain Sub-3-3 (2.9 g, yield: 68%).

(3) Sub  3-4 Synthetic example

Sub 3-3 (2.9 g, 9.6 mmol) and triphenylphosphine (7.5 g, 28.8 mmol) were dissolved in o-dichlorobenzene and refluxed for 24 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the concentrated product was separated by column chromatography to obtain 1.7 g (yield: 65%) of Sub 3-4.

(4) Compound 3-9 Synthetic example

Sub3-4 (1.7 g, 6.2 mmol) and Sub 3-5 (1.9 g, 6.2 mmol) were placed in toluene and Pd ₂ (dba) ₃ (0.3 g, 0.31 mmol), PPh ₃ (0.2 g, 0.62 mmol) and NaO t- Bu (1.8 g, 18.6 mmol) were added, respectively, and the mixture was refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 2.0 g (yield: 63%) of Compound 3-9.

Meanwhile, FD-MS values of the compounds 3-1 to 3-32 prepared according to the above Synthesis Example are shown in Table 2 below.

[Table 2]

III . (3) Synthetic example

Illustrative examples of the synthesis of compound 4-1 in the compound of formula 3 according to the present invention are shown in the following reaction scheme, but not limited thereto.

<Reaction Scheme 8>

3-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol) was dissolved in THF and then 9- (4,6-diphenyl-1,3,5-triazin- 3-yl) boronic acid (8.8 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol), NaO t- ), Water is added, and the mixture is refluxed with stirring. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 9.2 g (yield: 72%) of Compound 4-1

Meanwhile, the FD-MS values of the compounds 4-1 to 4-24 prepared according to the above Synthesis Example are shown in Table 3 below.

[Table 3]

IV . 4 Synthetic example

Illustrative examples of the compound 5-6 in the compound represented by the general formula (4) according to the present invention are shown in the following reaction scheme (9), but are not limited thereto.

<Reaction Scheme 9>

2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (7.8 g, 20 mmol) and Pd ₂ (dba) were dissolved in THF. ₃ (0.9 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol), NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL). After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 7.5 g (yield: 70%) of 5-6.

Meanwhile, FD-MS values of the compounds 5-1 to 5-12 prepared according to the above synthesis examples are shown in Table 4 below.

[Table 4]

Evaluation of manufacturing of organic electric device

[ Example  1] Green organic electroluminescent device ( Phosphorescent dopant )

An organic electroluminescent device was fabricated according to a conventional method using a compound according to an embodiment of the present invention as a luminescent dopant material in a light emitting layer. First, ITO layer (anode) formed on the glass substrate over the N ¹ - (naphthalen-2-yl) -N 4, N 4 -bis (4- (amino naphthalen-2-yl (phenyl)) phenyl) -N 1 - phenylbenzene-1,4-diamine (hereinafter abbreviated as "2-TNATA") was vacuum-deposited to form a 60 nm thick hole injection layer. Subsequently, 4,4-bis [ N - (1-naphthyl) -N -phenylamino] biphenyl (abbreviated as "NPD" hereinafter) was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer Respectively. The compound 3-9 of the present invention was doped as a host material and the compound 1-1 of the present invention was doped as a dopant in a weight ratio of 95: 5 on the hole transport layer, followed by vacuum evaporation at a thickness of 30 nm to form a light emitting layer. Next, aluminum (1,1'-biphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as "BAlq") was vacuum- to form a tris (8-quinolinol) aluminum (hereinafter referred to as "Alq _3" abbreviated to) a vacuum-deposited over the electron transport layer to form a 40nm thick on the hole blocking layer, the hole blocking layer. Thereafter, an electron injection layer was formed by depositing LiF, which is an alkali metal halide, to a thickness of 0.2 nm on the electron transport layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

[ Example  2] to [ Example  51] Green Organic Electroluminescent Devices Phosphorescent dopant )

Except for using one of the compounds 1-2 to 1-25 and 2-1 to 2-26 of the present invention described in the following Table 5 instead of the compound 1-1 of the present invention as a dopant material of the light emitting layer, An organic electroluminescent device was prepared.

[ Comparative Example  One]

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

&Lt; Comparative Compound 1 > Ir (ppy) ₃

Electroluminescence (EL) characteristics were measured by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 1 to 51 and Comparative Example 1 of the present invention, The T95 lifetime was measured using a lifetime measuring device manufactured by Mac Science Inc. at a luminance of 5000 cd / m 2. The measurement results are shown in Table 5 below.

[Table 5]

As can be seen from the results of Table 5, the organic electroluminescent device using the organic electroluminescent device material of the present invention can be produced by using the compound represented by the general formula (2) as a host of the luminescent layer, It was confirmed that the driving voltage was lower than that when Ir (ppy) ₃ as the comparative compound 1 was used as a dopant in the light emitting layer, and the efficiency and lifetime were remarkably improved.

This is because the host-dopant combination of the present invention has a better energy balance than the combination of the comparative compound dopant and the host, and the packing density of the compound of the present invention is better, resulting in a lower driving voltage of the device , The efficiency and the life span are remarkably increased.

[ Example  52] green organic electroluminescent device (mixed host + Phosphorescent dopant )

An organic electroluminescent device was fabricated according to a conventional method using a compound according to an embodiment of the present invention as a luminescent dopant material in a light emitting layer. First, a 2-TNATA film was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a 60 nm thick hole injection layer. Subsequently, NPD was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer. Compound 3-9 and 5-4 of the present invention were mixed on the hole transport layer to prepare a host material, doped with Compound 1-1 of the present invention as a dopant, at a weight ratio of 95: 5, and vacuum deposited to a thickness of 30 nm Thereby forming a light emitting layer. Next, BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer to form a hole blocking layer, and an electron transporting layer was formed by vacuum evaporation of Alq ₃ to a thickness of 40 nm on the hole blocking layer. Thereafter, an electron injection layer was formed by depositing LiF, which is an alkali metal halide, to a thickness of 0.2 nm on the electron transport layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

[ Example  53] to [ Example  72] green organic electroluminescent device (mixed host + Phosphorescent dopant )

Except that one of the compounds 1-2 to 1-21 of the present invention described in the following Table 6 was used instead of the compound 1-1 of the present invention as a dopant material of the light emitting layer, .

[ Example  73] to [ Example  100] green organic electroluminescent device (mixed host + Phosphorescent dopant )

Instead of the compound 3-9 and 5-4 of the present invention as the host material of the light emitting layer, the compounds 3-9 and 4-1 were mixed and used instead of the compound 1-1 of the present invention as the dopant of the light emitting layer. An organic EL device was prepared in the same manner as in Example 52 except that one of Inventive Compounds 1-21 to 1-25 and 2-1 to 2-24 was used.

[ Example  101 and [ Example  102] green organic electroluminescent device (mixed host + Phosphorescent dopant )

Compounds 4-1 and 5-4 were used instead of the compounds 3-9 and 5-4 of the present invention as the host material of the light emitting layer and the compound 1-1 of the present invention was used as a dopant material of the light emitting layer, An organic EL device was prepared in the same manner as in Example 52, except that the compound 2-25 or 2-26 of the present invention was used.

Electroluminescence (EL) characteristics were measured with a photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 52 to 102 of the present invention. The electroluminescence (EL) characteristics were measured at 5000 cd / The T95 lifetime was measured at the luminance using a life measuring instrument manufactured by Mac Science. The measurement results are shown in Table 6 below.

[Table 6]

As can be seen from the results of Table 6, the organic electroluminescent device using the organic electroluminescent device material of the present invention was used as a green luminescent layer material when a mixed host was used, compared to when using a single host, . This is because the bandgap is wider and the charge balance in the emissive layer is higher than that of the single host due to the two mixed hosts, and the efficiency and lifetime are increased.

[ Example  103] yellow organic electroluminescent device ( Phosphorescent dopant )

An organic electroluminescent device was fabricated according to a conventional method using a compound according to an embodiment of the present invention as a luminescent dopant material in a light emitting layer. First, a 2-TNATA film was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a 60 nm thick hole injection layer. Subsequently, NPD was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer. The compound 4-1 of the present invention was doped as a host material and the compound 1-1 of the present invention was doped as a dopant in a weight ratio of 95: 5 on the hole transport layer to form a light emitting layer by vacuum deposition to a thickness of 30 nm. Next, BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer to form a hole blocking layer, and an electron transporting layer was formed by vacuum evaporation of Alq ₃ to a thickness of 40 nm on the hole blocking layer. Thereafter, an electron injection layer was formed by depositing LiF, which is an alkali metal halide, to a thickness of 0.2 nm on the electron transport layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

[ Example  104] to [ Example  122] yellow organic electroluminescent device Phosphorescent dopant )

Except that the compounds 1-1 to 1-10 and 2-1 to 2-10 of the present invention described in the following Table 7 were used instead of the compound 1-1 of the present invention as a dopant material of the light emitting layer, An organic electroluminescent device was prepared.

[ Comparative Example  2]

An organic electroluminescence device was prepared in the same manner as in Example 103, except that the following compound 2 was used instead of the compound 1-1 of the present invention as a dopant material in the light emitting layer.

&Lt; Comparative Compound 2 > PO01

Electroluminescence (EL) characteristics were measured by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 103 to 122 and Comparative Example 2 of the present invention, The T95 lifetime was measured using a lifetime measuring device manufactured by Mac Science Inc. at a luminance of 5000 cd / m 2. The measurement results are shown in Table 7 below.

[Table 7]

As can be seen from the results of Table 7, the organic electroluminescent device using the organic electroluminescent device material of the present invention can be produced by using the compound represented by the formula 3 as a host of the luminescent layer and the compound represented by the formula 1 as a yellow dopant , It was confirmed that the driving voltage was lower and the efficiency and lifetime were remarkably improved when PO01 as Comparative Compound 2 was used as a dopant in the light emitting layer.

This is because the host-dopant combination of the present invention has a better energy balance than the combination of the comparative compound dopant and the host, as in Examples 1 to 51 of Table 5 above, and the packing density of the compound of the present invention is better, And the efficiency and the life span are remarkably 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 (13)

A first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode and including at least a light emitting layer,
Wherein the dopant of the light emitting layer comprises a compound represented by the following Formula 1,
Wherein the host of the light emitting layer comprises at least one of the compounds represented by the following Chemical Formulas 2 to 4:
&Lt; Formula 1 >

(Where A is

or

being)
&Lt; Formula 2 >< EMI ID =

In the above formula (1), the P ring of A is a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group containing N (nitrogen), Q ring is a substituted or unsubstituted C ₆ -C ₂₀ aryl group, and l Is an integer from 0 to 2, n is an integer from 0 to 4, and R ⁷ and R ⁸ are each independently of the other hydrogen; heavy hydrogen; An aryl group of C ₆ -C ₆₀ ; And at least one heteroatom selected from the group consisting of O, N, S, Si and P A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; A C ₁ -C ₅₀ alkoxy group; And an alkenyl group of C ₂ -C ₂₀ ,
A and b are each an integer of 0 or 1, m is an integer of 0 to 2, o and q are each an integer of 0 to 4, X and Y are independently of each other S, O, N (R '), C (R') (R ") or Si (R ') (R"), and R ⁹ to R ¹¹ independently of one another are i) deuterium; An aryl group of C ₆ -C ₆₀ ; And at least one heteroatom selected from the group consisting of O, N, S, Si and P A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; A C ₁ -C ₅₀ alkoxy group; An alkenyl group of C ₂ -C ₂₀ ; And -L ^a -N (R ^a ) (R ^b ); or ii) adjacent groups may combine with each other to form at least one ring, wherein R ⁹ to R ¹¹ are the same defined as defined above i), Ar ¹ is an aryl group of C ₆ -C _60; A fluorenyl group; And at least one heteroatom selected from the group consisting of O, N, S, Si and P A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; And -L ^a -N (R ^a ) (R ^b )
In Formula 3, Z ¹ to Z ¹⁶ are independently a C (R), or N to each other, Z ⁵ to Z ^8, at least one of the at least one, and Z ⁹ to Z ¹² of which is a C (R), Z ¹ to Z ^When R is C (R) and adjacent to each other, adjacent Rs may be bonded to each other to form a ring; R is hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; And at least one heteroatom selected from the group consisting of O, N, S, Si and P A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; And ^{-L a -N (R a) (} R b); is selected from the group consisting of, W is N (Ar ^3), an S, O or C (R ') (R " ), Ar 2 and Ar ³ is Each independently represent a C ₆ -C ₆₀ aryl group, a fluorenyl group, and at least one hetero atom selected from the group consisting of O, N, S, Si and P A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; And an arylamine group having from _{6 to 60} carbon atoms,
R ¹ to R ^{6 in} the formula (1) and R ¹² to R ²³ in the formula (4) independently of one another are i) hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; And at least one heteroatom selected from the group consisting of O, N, S, Si and P A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; A C ₁ -C ₅₀ alkoxy group; An alkenyl group of C ₂ -C ₂₀ ; And ^{-L a -N (R a) (} R b); selected from the group consisting of or, or ii) between adjacent groups combine with each other (in the case of the general formula 4 R ¹² and R ^23, R ¹⁵ and R ^16, R ¹⁹ and R ²⁰ are bonded to each other), at least one of R ¹ to R ⁶ and R ¹² to R ²³ which do not form a ring is defined as defined in the above i) ,
L ² in the formula 2 of L ¹ and Formula 3 are independently a single bond to each other; C ₆ -C ₆₀ arylene groups; A C ₂ -C ₆₀ heteroarylene group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; And A divalent aliphatic hydrocarbon group,
Wherein R 'and R "are independently of each other, i) hydrogen, containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; the aryl group of C ₆ -C ₆₀ A heterocyclic group of C ₂ -C _60; A C ₁ -C ₅₀ alkyl group; And an alkenyl group of C ₂ -C _60; selected from the group consisting of or, or ii) may bond to one another to form a ring,
L ^a is a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And a C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P;
R ^a and R ^b are independently of each other a C ₆ -C ₆₀ aryl group; A fluorenyl group; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And a C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P;
The aryl group, the fluorenyl group, the heterocyclic group, the fused ring group, the aliphatic hydrocarbon group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxyl group, the aryloxyl group, the arylene group and the fluorenylene group are each independently selected from deuterium; A halogen group; A silane group; 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; C ₆ -C ₂₀ An 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 ; And an arylalkenyl group having from _{8 to 20} carbon atoms. The method according to claim 1,
Wherein the dopant of the light emitting layer is at least two kinds of compounds of the compound represented by the formula (1). The method according to claim 1,
Wherein the host of the light emitting layer is at least two kinds of compounds represented by the general formulas (2) to (4). The method according to claim 1,
Wherein at least one of R ¹ to R ⁶ in Formula 1 is a C ₁ -C ₂₀ alkyl group. The method according to claim 1,
The organic electroluminescent device according to claim 1, wherein the compound represented by Formula 1 is represented by one of the following formulas:
&Lt; Formula 5 >< EMI ID =

&Lt; Formula 7 &gt;&lt; EMI ID =

&Lt; Formula 9 >< EMI ID =

In the general formulas (5) to (10), R ¹ to R ⁸ , 1 and n are defined as defined in claim 1. The method according to claim 1,
Wherein the compound represented by Formula 1 is one of the following compounds:

. The method according to claim 1,
Wherein the compound represented by Formula 2 is one of the following compounds:

. The method according to claim 1,
Wherein the compound represented by Formula 3 is one of the following compounds:

. The method according to claim 1,
Wherein the compound represented by Formula 4 is one of the following compounds:

. The method according to claim 1,
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. The method according to claim 1,
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 according to any one of claims 1 to 11; And a control unit for driving the display device. 13. The electronic device according to claim 12, wherein the organic electroluminescent device is at least 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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