KR20150030511A - Organic electronic element using a compound for organic electronic element, and an electronic device thereof - Google Patents

Abstract

Provided in the present invention are a novel compound capable of improving light emitting efficiency, stability, and life of an element, an organic electronic element using the same, and an electronic device thereof. The organic electronic element includes a first electrode; a second electrode; and an organic substance layer located between the first electrode and the second electrode and including at least light emitting layer, wherein a dopant on the light emitting layer includes a compound presented by chemical formula 1, and a host thereof includes at least one among compounds presented by chemical formula 2 to 4.

Description

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

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

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

A material used as an organic material layer in an organic electric device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight, and may be classified into a phosphorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

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

In organic electroluminescent devices, the most problematic is the lifetime and the efficiency. As the display becomes larger, such efficiency and life time problems 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, it is impossible to maximize the efficiency by merely improving the organic material layer. The energy level and T1 value of each organic material layer, the intrinsic properties (mobility, interface characteristics, etc.) It can achieve long life and high efficiency 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 fully 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 layer material for an organic electric device has not been sufficiently developed yet. Particularly, development of a host material and a dopant material of a light emitting layer is urgently required.

An object of the present invention is to provide an organic electronic device and an electronic device using the compound capable of improving the light emitting efficiency, the low driving voltage, the high heat resistance, the color purity and the life of the device.

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 the present invention, it is possible to achieve a high luminous efficiency, a low driving voltage, and a high heat resistance of the device, and can greatly improve the color purity and lifetime of the device.

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, terms such as first, second, A, B, (a), and (b) may 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."

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 "heteroalkyl group" as used herein means that at least one of the carbon atoms constituting the alkyl group is replaced by a heteroatom.

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.

The term "alkenoyl group "," alkenoyl group ", "alkenyloxy group ", or" alkenyloxy group "as used in the present invention means an alkenyl group to which an oxygen radical is attached, , But is not limited thereto.

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, 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 "heteroalkyl ", as used herein, unless otherwise indicated, means an alkyl comprising one or more heteroatoms. 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 indicated, includes one or more heteroatoms, has from 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings and includes a heteroaliphatic ring and hetero 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.

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.

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 indicated, the term "ring" as used herein refers to a fused ring of aliphatic rings of 3 to 60 carbon atoms, aromatic rings of 6 to 60 carbon atoms, heterocyclic rings of 2 to 60 carbon atoms, or combinations thereof, Or an 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.

Unless otherwise specified, the term "carbonyl" as used herein refers to -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, A cycloalkyl group of 2 to 20 carbon atoms, an alkenyl group of 2 to 20 carbon atoms, an alkynyl group of 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise indicated, the term "ether" used in the present invention refers to -RO-R 'wherein R or R' are each independently of the other hydrogen, an alkyl group of 1-20 carbon atoms, An aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

One also no explicit description, the terms in the "unsubstituted or substituted", "substituted" is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C for use in the present invention 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 group, C ₂ ~ C of ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron Means a group substituted with at least one substituent selected from the group consisting of a halogen atom, a halogen atom, a cyano group, a germanium group, and a C ₂ to C ₂₀ heterocyclic group.

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 illustration of an organic electroluminescent device according to an embodiment of the present invention.

1, an organic electroluminescent device 100 according to the present invention includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110, ) Comprising an organic compound layer comprising a compound according to the present invention. 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 the present invention may further include 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.

The compound according to the present invention applied to the organic material layer may be a host or dopant of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, the light emitting layer 150, It can be used as a material.

The organic electroluminescent device according to an embodiment of the present invention can be manufactured using a physical vapor deposition (PVD) method. For example, the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, and an electron transporting layer 160 and an electron injection layer 170, and then depositing a material usable as the cathode 180 on the organic layer.

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 the present invention may be of a top 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 the present invention may be one of an organic electroluminescent (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

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.

According to an embodiment of the present invention, there is provided a plasma display panel 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 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) >

In Formula 1,

R ¹ to R ⁸ are independently selected from the group consisting of: i) independently of one another hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₆₀ ; And L ^a -N (R _a ) (R _b ); wherein L ^a is a single bond, C ₆ to C ₆₀ arylene group, fluorenylene group, C ₃ to C ₆₀ A divalent fused ring group of an aromatic ring of C ₆ to C ₆₀ and a divalent heterocyclic group of C ₂ to C ₆₀ containing at least one hetero atom of O, N, S, Si and P; , R _a and R _b are independently selected from the group consisting of a C ₆ to C ₆₀ aryl group, a fluorenyl group, a fused ring of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring And a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; or ii) a group selected from the group consisting of R ¹ and R ² , R ² , R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ or R ⁷ and R ⁸ may combine with each other to form at least one ring, is a C ₃ ~ C ₆₀ alicyclic, C ₆ ~ C ₆₀ of aromatic Lee, refers to a heterocycle or a combination thereof is a fused ring of C ₂ ~ C _60, and a saturated or unsaturated ring.

In the above formula (1), 1 is an integer of 1 to 3, A is represented by the above formula (1-1) or (1-2) a substituted or unsubstituted heterocyclic group of C ₂ ~ C ₂₀ ring, Q is a ring C (carbon), an aromatic hydrocarbon (aryl), a substituted or unsubstituted C ₆ ~ C ₂₀ containing. At this time, N (nitrogen) in the P ring forms a coordination bond (indicated by a dotted line) with the Ir (iridium) and C (carbon) in the Q ring forms a covalent bond have.

When the P ring and the Q ring are each substituted, i) each substituent is independently selected from the group consisting of 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; And a C ₁ to C ₃₀ alkoxyl group, or ii) when each substituent is plural, adjacent substituents are bonded to each other to form at least one ring, or iii) a substituent of the P ring and a substituent of the Q ring The substituents may be bonded to each other to form a ring.

On the other hand, one of the two O (oxygen) in the formula (1-2) forms a coordination bond (indicated by a dotted line) with the Ir (iridium) and the other forms a covalent bond with the Ir (iridium) Display) can be formed.

In the above formula (1-2), R ⁹ and R ¹⁰ independently represent hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₆₀ ; And _{^{-L b -N (R c) (}} R d); may be selected from the group consisting of. Here, L ^b , R _c and R _d may be the same as defined for L ^a , R _a and R _b , respectively.

(2)

In Formula 2,

a and b are each an integer of 0 or 1, a + b is 1 or more,

X and Y are independently of each other a single bond; S; O; NR ';CR'R is selected from the group consisting of wherein R 'and R "are each independently of the others hydrogen;;"; and SiR'R "C ₆ ~ ₆₀ aryl group of C; O, N, S, at least one of Si and P A C ₂ to C ₆₀ heterocyclic group containing one hetero atom, and a C ₁ to C ₅₀ alkyl group,

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

R ¹¹ to R ¹³ are the same or different from each other when m is 2, and o or q is an integer of 2 to 4, and i) independently of one another are deuterium; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₆₀ ; And L ^c -N (R _e ) (R _f ), wherein L ^c , R _e and R _f are the same as defined for L ^a , R _a and R _b , respectively, Or ii) a plurality of R ¹¹ to R ¹³ may combine with each other to form at least one aromatic ring together with the carbon to which they are attached, wherein the aromatic ring formed may be C ₆ to C ₆₀ aryl.

Ar ¹ is a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₆₀ ; And -L ^d -N (R _g ) (R _h ); Here, L ^d , R _g and R _h may be the same as the definitions of L ^a , R _a and R _b , respectively.

L ¹ is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A C ₂ to C ₆₀ heteroarylene group containing at least one hetero atom selected from O, N, S, Si and P; And a divalent aliphatic hydrocarbon having ₁ to ₆₀ carbon atoms.

(3)

In Formula 3,

Z ¹ to Z ¹⁶ are independently selected from the group consisting of (i) independently of one another CR; Or N, provided that at least one of Z ⁵ to Z ⁸ and at least one of Z ⁹ to Z ¹² is CR, wherein one of Z ⁵ to Z ⁸ and one of Z ⁹ to Z ¹² is C If the place of the box in combination with L ^2), or ⅱ) Z ¹ to Z Z a ¹⁶ of the neighbor in combination with the each of CR has to form an aromatic ring together with the bonded and those bonded to each other adjacent group carbon, Wherein the aromatic ring formed may be C ₆ -C ₆₀ aryl.

Wherein R is hydrogen, 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; And -L ^e -N (R _i ) (R _j ). Here, L ^e R _i and R _j may have the same definitions as L ^a , R _a and R _b , respectively.

L ² is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A C ₂ to C ₆₀ heteroarylene group containing at least one hetero atom selected from O, N, S, Si and P; And a divalent aliphatic hydrocarbon having ₁ to ₆₀ carbon atoms,

W is N (Ar ^3); O; And S; &lt; / RTI &gt;

Ar ² and Ar ³ are each independently a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₆₀ ; And -L ^f -N (R _k ) (R ₁ ). Here, L ^f , R _k and R ₁ may be the same as defined above for L ^a , R _a and R _b , respectively.

         &Lt; Formula 4 >

In Formula 4,

R ¹⁴ to R ²⁵ are independently selected from the group consisting of: i) independently of one another hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₆₀ ; And _{^{-L g -N (R m) (}} R n); selected from the group consisting of or (Here, the above L ^g, R _m and R _n are each as defined the above L ^a, R _a and R _b) Or ii) one or more of 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, R ²³ and R ^24, R ²⁴ and R ²⁵ or R ²⁵ and R ¹⁴ may form at least one ring by combining to each other, wherein "ring" is C ₃ ~ C ₆₀ of Refers to a fused ring that is an aliphatic ring, a C ₆ to C ₆₀ aromatic ring, a C ₂ to C ₆₀ hetero ring, or a combination thereof, and includes saturated or unsaturated rings.

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 respectively deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; L ^h -N (R _o ) (R _p ) wherein L ^h , R _o and R _p are each as defined above for L ^a , R _a and R _b ; An alkyl thio group of C ₁ to C ₂₀ ; A C ₁ to C ₂₀ alkoxyl group; An alkyl group having ₁ to ₂₀ carbon atoms; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₆ to C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A heterocyclic group of C ₂ ~ C _20; A C ₃ to C ₂₀ cycloalkyl group; An arylalkyl group having ₇ to ₂₀ carbon atoms and an arylalkenyl group having ₈ to ₂₀ carbon atoms, and these substituents may be further bonded to each other to form a ring, Refers to a fused ring that is an aliphatic ring of C ₃ to C ₆₀ , a C ₆ to C ₆₀ aromatic ring, a C ₂ to C ₆₀ hetero ring, or a combination thereof, and includes saturated or unsaturated rings.

In another embodiment of the present invention, the dopant of the light-emitting layer includes the compound represented by Formula 1, and the host of the light-emitting layer is a compound in which two or more different compounds among the compounds represented by Formulas 2 to 4 are mixed And an organic electroluminescent device. For example, it may be a mixture of two different compounds represented by the formulas (2) and (3), or a mixture of two or more different compounds represented by the compound (2).

In another embodiment of the present invention, the compound represented by the formula (1) may be one represented by the following formulas (5) to (9).

(5) The compound of the formula (6)

(7) The compound of formula (8)

(9)

In the above formulas (5) to (9)

R ¹ to R ¹⁰ and l are the same as defined for the R ¹ to R ¹⁰ l and the formula (1),

R ²⁶ to R ³³ are independently selected from the group consisting of: i) independently of each other hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₆₀ ; And _{^{-L i -N (R q) (}} R r); or selected from the group consisting of (wherein the definition of the L ^a, R _a and R _b wherein L ^i, R _q and R _r are the formula (I), respectively and Or ii) R ²⁶ and R ²⁷ , R ²⁷ and R ²⁸ , R ²⁸ and R ²⁹ , R ²⁹ and R ³⁰ , R ³⁰ and R ³¹ , R ³¹ and R ³² or R ³² and R ³³ May be combined to form at least one ring.

The ring at the time of ring formation means a C ₃ to C ₆₀ aliphatic ring, a C ₆ to C ₆₀ aromatic ring, or a C ₂ to C ₆₀ hetero ring.

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 another embodiment of the present invention, a light-efficiency-improvement layer is 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.

In another embodiment of the present invention, the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process and a roll-to-roll process do.

In another embodiment of the present invention, there is provided a method of fabricating a semiconductor device, 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.

In yet another embodiment of the present invention, an organic electronic device according to the present invention includes at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT) It can be one.

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

Synthesis of the compound was carried out as follows.

Ⅰ. Synthesis of formula (1)

The compound represented by the formula (1) according to the present invention can be synthesized by the reaction path of the following Reaction Scheme 1 or Reaction Scheme 2, but is not limited thereto.

&Lt; Reaction Scheme 1 > When l is 3

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

One. Sub  Synthesis of 1

Sub 1 in the above Reaction Scheme 1 may be synthesized by the reaction path of the following Reaction Scheme 3, but is not limited thereto.

<Reaction Scheme 3>

2-chloropyridine (1 eq.) Was dissolved in THF, and then phenylboronic acid (1 equivalent), Pd (PPh ₃ ) ₄ (0.05 eq.), K ₂ CO ₃ . 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 a product.

Meanwhile, examples of Sub 1 are as follows, but the present invention is not limited thereto, and their FD-MSs are shown in Table 1 below.

[Table 1]

2. Product  Synthesis of 1

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

(One) Product  1-4 Synthesis

<Reaction Scheme 4>

Ir (acac) ₃ (489.54 g, 20 mmol) was added to 2- (m-tolyl) pyridine (13.5 g, 80 mmol) and refluxed with glycerol under nitrogen for 24 hours. 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 42.5 g (yield: 76%) of the final compound.

(2) Product  1-6 synthesis

<Reaction Scheme 5>

Ir (acac) ₃ (489.54 g, 20 mmol) was added to 2,4-diphenylpyridine (18.5 g, 80 mmol) and refluxed with 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 3 hours to obtain 52.5 g (yield: 74%) of the final compound.

3. Product  Synthesis of 2

The product 2 of the above Reaction Scheme 2 can be synthesized by the reaction route of the following Reaction Scheme 6, but is not limited thereto.

<Reaction Scheme 6>

(One) Sub  2-1 Synthesis

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 nitrogen in a solution of 2-ethoxy ethanol: H ₂ O in a ratio of 3: 1. After the completion of the reaction, the obtained solid substance was filtered, purified through column chromatography, and dried under a vacuum pump for 3 hours to obtain a final compound.

(2) Product  2 synthesis

Pentane-2,4-dione (10 eq.), Na ₂ CO ₃ (10 eq.) And 2-ethoxy ethanol were added to Sub 2-1 (1 eq.) And reacted at 130 ° C for 24 hours under nitrogen. After the completion of the reaction, the obtained solid substance was filtered, purified through column chromatography, and dried under a vacuum pump for 3 hours to obtain a final compound.

(3) Product  2-2 Synthesis

<Reaction Scheme 7>

2,2,6,6-tetramethylheptane-3,5-dione (10 eq.), Na ₂ CO ₃ (10 eq.) And 2-ethoxy ethanol were added to the Ir compound (1 eq.) 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 the final compound 2-2.

(4) Product  2-6 Synthesis

<Reaction Scheme 8>

Pentane-2,4-dione (10 eq.), Na ₂ CO ₃ (10 eq.) And 2-ethoxy ethanol were added to the Ir compound (1 eq.) 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 vacuum pump for 3 hours to obtain the final compound 2-6.

4. Product  Synthesis of 3

Product 2 (1 eq.) And Sub 2 (2 eq.) Were added and microwaved with glycerol for 20 minutes. After the completion of the reaction, the obtained solid substance was filtered, purified through column chromatography, and dried under a vacuum pump for 3 hours to obtain a final compound.

Here, Sub 2 is the same as the example of Sub 1.

(One) Product  2-7 Synthesis

<Reaction Scheme 9>

The ancillary ligand, 2 - ([1,1'-biphenyl] -3-yl) pyridine (9.3 g, 40 mmol) was added to the ligand Ir compound (12.2 g, 20 mmol) microwave. 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 8.8 g (yield: 60%) of the final compound.

(2) Product  2-39 Synthesis

<Reaction formula 10>

([l, l'-biphenyl] -3-yl) pyridine (6.2 g, 40 mmol) was added to the ligand Ir compound (18.1 g, 20 mmol) and heated with glycerol for 20 min at 240 ° C in microwave microwave. 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 11.3 g (yield: 58%) of the final compound.

Ⅱ. Synthesis of Formula 2

The synthesis examples of Product 3-9 among the final products represented by Formula 2 according to the present invention can be synthesized by the reaction path of the following Reaction Scheme 11, but are not limited thereto.

<Reaction Scheme 11>

(One) Sub  3-2 Synthesis

Sub 3-1 was dissolved in anhydrous THF, the temperature of the reaction was lowered to -78 ° C, n-BuLi (2.5M in hexane) was slowly added dropwise, and the reaction was stirred at 0 ° C for 1 hour. Then, the temperature of the reaction was lowered to -78 ° C, trimethyl borate was added dropwise, and the mixture was stirred at room temperature for 12 hours. When the reaction was completed, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with ether. Water in the reaction mixture 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 the desired Sub 3-2.

(2) Sub  3-3 Synthesis

Sub 3-2 and 1-iodo-2-nitrobenzene, Pd (PPh ₃ ) ₄ and K ₂ CO ₃ were dissolved in anhydrous THF and a small amount of water and 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 the desired Sub 3-3.

(3) Sub  3-4 Synthesis

Sub 3-3 and triphenylphosphine were dissolved in o-dichlorobenzene and refluxed for 24 hours. When the reaction was completed, the solvent was removed by distillation under reduced pressure, and the concentrated product was separated by column chromatography to obtain the desired Sub 3-4.

(4) Product  3-9 synthesis

Pd ₂ (dba) ₃ (0.05 eq.), PPh ₃ (0.1 eq.) And NaO t -Bu (3 eq.) Were added to the toluene in the same manner as Sub 3-4 (1 eq.) And Sub 3-5 , And the mixture is stirred and 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 purified by silicagel column and recrystallized to obtain Product 3-9.

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

[Table 2]

Ⅲ. Synthesis of Formula 3

Examples of the synthesis of Product 4-1 among the final products represented by Formula 3 according to the present invention can be synthesized by the reaction path of the following Reaction Scheme 12, but are not limited thereto.

<Reaction Scheme 12>

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 (PPh ₃ ) ₄ (0.03 eq.), K ₂ CO ₃ (3 eq.) And water. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 9.2 g (yield: 72%) of the product.

Meanwhile, the FD-MS values of the compounds 4-1 to 4-24 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[Table 3]

IV. Synthesis of Formula 4

Synthesis examples of Product 5-6 among the final products represented by Formula 4 according to the present invention can be synthesized by the reaction path of the following Reaction Scheme 13, but are not limited thereto.

<Reaction Scheme 13>

2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (7.8 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.03 eq.), K ₂ CO ₃ (3 eq.) And water are added, and the mixture is refluxed with stirring. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 7.5 g (yield: 70%) of the product.

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

[Table 4]

Evaluation of manufacturing of organic electric device

[ Experimental Example  Ⅰ] Green organic electroluminescent device (phosphorescence Dopant )

First, N ¹ on the ITO layer (anode) formed on the glass substrate - (naphthalen-2-yl) -N 4, N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N 1 phenylbenzene-1,4-diamine (hereinafter abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 60 nm to form a hole injecting layer, and then 4,4-bis [N- (1-naphthyl ) -N-phenylamino] biphenyl (hereinafter abbreviated as NPD) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. Next, a compound (3-9) represented by the formula (2) of the present invention was doped as a host material on the hole transport layer and a compound represented by the formula (1) of the present invention was doped as a dopant in a ratio of 95: Respectively. Subsequently, aluminum (1,1'-biphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited on the light- (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer. Then, LiF, an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

[ Comparative Example  I]

An organic electroluminescent device was fabricated in the same manner as in Experimental Example I, except that the following Comparative Compound (1) Ir (ppy) ₃ was used as a dopant material.

Comparative compound (1) Ir (ppy) ₃

A forward bias DC voltage was applied to the organic electroluminescent devices prepared in Experimental Example I (Experimental Examples 1 to 66) and Comparative Example I (Comparative Example 1) thus prepared, and photoresearch was performed. The electroluminescence (EL) characteristics were measured with PR-650, and the T95 lifetime was measured by a lifetime measuring device manufactured by Mac Science Inc. at a luminance of 5000 cd / m 2.

Table 5 below shows device fabrication and evaluation results for Experimental Example I (Experimental Examples (1) to (66)) and Comparative Example (Comparative Example (1)) to which the compound according to the present invention was applied .

[Table 5]

As can be seen from the results of the above 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 formula 2 as a host and the compound represented by the formula 1 as a green dopant material It was confirmed that the use of Comparative Compound (1) Ir (ppy) ₃ exhibited lower driving voltage, higher efficiency, and longer lifetime than that when Ir (ppy) ₃ was used as a dopant. It is considered that the combination of the host and the dopant of the present invention has a good energy balance, thereby lowering the driving voltage of the device and increasing the efficiency and lifetime.

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

First, 2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to a thickness of 60 nm to form a hole injection layer, and then a hole transport layer was formed by vacuum depositing NPD on the hole injection layer to a thickness of 60 nm. Next, a material obtained by mixing the compound (3-9) represented by the formula (2) of the present invention and the compound (5-4) represented by the formula (4) as a host material on the hole transport layer is mixed with the compound represented by the formula Was doped in a weight ratio of 95: 5 to deposit a light emitting layer with a thickness of 30 nm. Subsequently, the vacuum-deposited to BAlq on the light-emitting layer to the thickness of 10nm to form a hole blocking layer, and Alq ₃ on the hole blocking layer was formed as an electron transporting layer 40nm thick. Then, LiF, an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

A forward bias DC voltage was applied to the organic electroluminescent devices prepared in Experimental Example II (Experimental Examples 67 to 87) thus prepared, and electroluminescence (EL) characteristics were measured with a PR-650 of a photoresearch company And the T95 lifetime was measured using a life measuring instrument manufactured by Mac Science Inc. at a luminance of 5000 cd / m 2.

Table 6 below shows device fabrication and evaluation results for Experimental Example II (Experimental Examples 67 to 87) to which the compound according to the present invention was applied.

[Table 6]

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

First, 2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to a thickness of 60 nm to form a hole injection layer, and then a hole transport layer was formed by vacuum depositing NPD on the hole injection layer to a thickness of 60 nm. Next, a material obtained by mixing a compound (3-9) represented by the formula (2) of the present invention and a compound (4-1) represented by the formula (3) as a host material on the hole transport layer is used as a dopant material, Was doped in a weight ratio of 95: 5 to deposit a light emitting layer with a thickness of 30 nm. Subsequently, the vacuum-deposited to BAlq on the light-emitting layer to the thickness of 10nm to form a hole blocking layer, and Alq ₃ on the hole blocking layer was formed as an electron transporting layer 40nm thick. Then, LiF, an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

A forward bias DC voltage was applied to the organic electroluminescent devices prepared in Experimental Example III (Experimental Examples 88 to 115) thus prepared, and electroluminescence (EL) characteristics were measured with PR-650 of a photoresearch company And the T95 lifetime was measured using a life measuring instrument manufactured by Mac Science Inc. at a luminance of 5000 cd / m 2.

Table 7 below shows the device fabrication and evaluation results for Experiment Example III (Experimental Examples (88) to (115)) to which the compound according to the present invention was applied.

[Table 7]

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

First, 2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to a thickness of 60 nm to form a hole injection layer, and then a hole transport layer was formed by vacuum depositing NPD on the hole injection layer to a thickness of 60 nm. Next, a material obtained by mixing the compound (4-1) represented by the formula (3-1) and the compound (5-4) represented by the formula (4) as the host material on the hole transport layer is mixed with the compound represented by the formula Was doped in a weight ratio of 95: 5 to deposit a light emitting layer with a thickness of 30 nm. Subsequently, the vacuum-deposited to BAlq on the light-emitting layer to the thickness of 10nm to form a hole blocking layer, and Alq ₃ on the hole blocking layer was formed as an electron transporting layer 40nm thick. Then, LiF, an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

A forward bias DC voltage was applied to the organic electroluminescence devices manufactured in Experimental Example IV (Experimental Examples 116 to 132) thus prepared, and electroluminescence (EL) characteristics were measured with PR-650 of a photoresearch company And the T95 lifetime was measured using a life measuring instrument manufactured by Mac Science Inc. at a luminance of 5000 cd / m 2.

Table 8 below shows device fabrication and evaluation results for Experiment Example IV (Experiments (116) to (132)) to which the compound according to the present invention was applied.

[Table 8]

As can be seen from the results of the above [Table 6] to [Table 8], the organic electroluminescent device using the organic electroluminescent device material of the present invention is a mixture of the compound represented by the formula 2 and the compound represented by the formula 4 , A mixture of the compound represented by the general formula (2) and the compound represented by the general formula (3), and a mixture of the compound represented by the general formula (3) and the compound represented by the general formula (4) It can be seen that it is used as a material for the light emitting layer rather than the case where it is used, thereby improving the light emitting efficiency, the driving voltage and the lifetime. It is considered that the bandgap is wider and the charge balance in the light emitting layer is higher than that of the single host due to the two mixed hosts, thereby increasing the efficiency and lifetime.

[ Experimental Example  V] yellow organic electroluminescent device (phosphorescence Dopant )

First, 2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to a thickness of 60 nm to form a hole injection layer, and then a hole transport layer was formed by vacuum depositing NPD on the hole injection layer to a thickness of 60 nm. Next, a compound (4-1) represented by the formula (3) of the present invention was doped as a host material on the hole transport layer and doped with a compound represented by the formula (1) of the present invention as a dopant in a weight ratio of 95: Respectively. Subsequently, the vacuum-deposited to BAlq on the light-emitting layer to the thickness of 10nm to form a hole blocking layer, and Alq ₃ on the hole blocking layer was formed as an electron transporting layer 40nm thick. Then, LiF, an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

[ Comparative Example  II]

An organic electroluminescent device was fabricated in the same manner as in Experimental Example V, except that the following Comparative Compound (2) PO01 was used as a dopant material.

Comparative compound (2) PO01

A forward bias DC voltage was applied to the organic electroluminescent devices prepared in Experimental Example V (Experimental Examples 133 to 174) and Comparative Example II (Comparative Example 2) thus prepared, and photoresearch was performed. The electroluminescence (EL) characteristics were measured with PR-650, and the T95 lifetime was measured by a lifetime measuring device manufactured by Mac Science Inc. at a luminance of 5000 cd / m 2.

Table 9 below shows device fabrication and evaluation results for Experimental Example V (Experimental Examples (133) to (174)) and Comparative Example (Comparative Example (2)) to which the compound according to the present invention was applied .

[Table 9]

As can be seen from the results of Table 9, the organic electroluminescent device using the organic electroluminescent device material of the present invention uses the compound represented by Formula 3 as a host and the compound represented by Formula 1 as a yellow dopant , Higher efficiency and longer lifetime than the case where the compound (2) PO01 was used as a dopant. It is considered that the combination of the host and the dopant of the present invention has a good energy balance, thereby lowering the driving voltage of the device and increasing the efficiency and lifetime.

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

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

Claims (11)

A 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 compound represented by any one of the following general formulas (2) to (4).
&Lt; Formula 1 >

(Where A is

or

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

,

,

[In the above formula (1), 1 is an integer of 1 to 3, and the A to P ring is a substituted or unsubstituted C ₂ to C ₂₀ heterocyclic ring containing nitrogen, and the Q ring is a substituted or unsubstituted C ₆ to C ₂₀ And R &lt; ⁹ &gt; and R &lt; ¹⁰ &gt; are each independently of the other hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₆₀ ; And -LN (R &lt; ^a &gt;) (R &lt; ^b &gt;);
Wherein a and b are each an integer of 0 or 1 (provided that a + b is 1 or 2), m is an integer of 0 to 2, o and q are integers of 0 to 4, X And Y are independently of each other a single bond, S, O, N (R '), C (R') (R ") or Si (R ' A C ₆ to C ₆₀ aryl group, a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P, and a C ₁ to C ₅₀ alkyl group; Selected from the group consisting of
In Formula 3, W is N (Ar ³ ), O, or S; Z ¹ to Z ¹⁶ are independently a C (R) to each other, or N, single Z ⁵ to Z ⁸ and at least one Z ⁹ to Z ^12, at least one of which is C (R), and of Z ¹ to Z ¹⁶ C ( R, and neighboring R's may bond to each other to form a ring; R is hydrogen; 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; And -LN (R &lt; ^a &gt;) (R &lt; ^b &gt;);
R ¹ to R ⁸ in Formula (1), R ¹¹ to R ^{13 in} Formula (2), and R ¹⁴ to R ²⁵ in Formula (4) are independently selected from the group consisting of: i) heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₆₀ ; And -LN (R ^a ) (R ^b ); or ii) adjacent groups are bonded to each other (in the case of formula (1), R ⁴ and R ⁵ are bonded to each other, R ¹⁴ and R ²⁵ , R ²¹ and R ²² , and R ¹⁷ and R ¹⁸ bond to each other) to form at least one ring,
An aryl group of formula (2) of the Ar ¹ and Ar ² in the formula (3) is independently C ₆ ~ C ₆₀ to each other; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₆₀ ; And -LN (R &lt; ^a &gt;) (R &lt; ^b &gt;);
L ^{1 in} formula (2) and L ² in formula (3) independently of one another are a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P;
L is independently a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P, and R ^a and R ^b are independently selected from the group consisting of C ₆ to C An aryl group of ₆₀ ; A fluorenyl group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P;
(Wherein 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 aryloxy group, the arylene group and the fluorenylene group are each independently of the others, A siloxane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, -LN (R ^a ) (R ^b ), a C ₁ to C ₂₀ alkylthio group, a C ₁ to C ₂₀ alkoxyl group, a C alkyl group of ₁ ~ C _20; C ₂ ~ of the C ₂₀ alkenyl group; an aryl group of a C ₆ ~ C ₂₀ substituted with heavy hydrogen;; C ₂ ~ C ₂₀ alkynyl of; an aryl group of C ₆ ~ C ₂₀ fluorenyl group , A C ₂ to C ₂₀ heterocyclic group, a C ₃ to C ₂₀ cycloalkyl group, a C ₇ to C ₂₀ arylalkyl group, and a C ₈ to C ₂₀ arylalkenyl group, have)] The method according to claim 1,
Wherein the host of the light emitting layer is a mixture of at least two different compounds among the compounds represented by the general formulas (2) to (4). The method according to claim 1,
The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (1) is one of the following formulas (5) to (9).
(5) The compound of the formula (6)

(7) The compound of formula (8)

(9)

[In the above formulas (5) to (9), R ²⁶ to R ³³ are independently selected from the group consisting of i) independently of each other hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₆₀ ; And -LN (R ^a ) (R ^b ); or ii) R ¹ to R ¹⁰ , l, L, R ^a and R ^b each are the same 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,
And an optical efficiency improving 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 method according to claim 1,
Wherein the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process. A display device comprising the organic electroluminescent device according to any one of claims 1 to 9; And
And a control unit for driving the display device. 11. The method of claim 10,
Wherein the organic electronic device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

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