KR20150064410A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides a novel compound which can improve light emitting efficiency, stability, and durability of an element, an organic electronic element, and an electronic device thereof. The organic electronic element comprises: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, wherein the compound is included in the organic layer.

Description

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

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 may have a multi-layer 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 can be classified into a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material depending on functions.

One of the biggest problems in organic electronic devices is the lifetime and the efficiency. As the display becomes larger, such efficiency and lifetime problems must be solved.

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 occurring during driving is reduced. As a result, And the like. However, simply improving the organic material layer can not maximize the efficiency. This is because the energy level and T ₁ value between each organic layer, the intrinsic properties (mobility, interfacial properties, etc.) of the materials, etc., Because.

Generally, electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination.

However, the holes migrate faster than the electrons, and the excitons generated in the light emitting layer are transferred to the electron transporting layer, resulting in charge unbalance in the light emitting layer and light emission at the electron transporting layer interface.

When light is emitted from the interface of the electron transport layer, color purity and efficiency of the organic electroluminescent device are lowered. In particular, when the organic electroluminescent device is manufactured, the stability of the organic electroluminescent device is deteriorated and the lifetime of the organic electroluminescent device is shortened. Therefore, it is necessary to develop an electron transporting material which has a high temperature stability and a high electron mobility and has a high T1 value to improve the hole blocking ability.

The present invention relates to an organic electronic device having high electron mobility and high temperature stability, a compound having a more efficient electron transporting ability at a high T ₁ value and improved efficiency, lifetime and color purity using such a compound, and an electronic device And an object of the present invention is to provide a device.

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

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

According to the present invention, it is possible to provide a compound having a high electron mobility and a high temperature stability and a more efficient electron transporting ability at a high T ₁ value, and the efficiency, lifetime and color purity of the device can be improved by using such a compound.

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 in the present invention, 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 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.

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 a dopant of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, It can be used as a material. Preferably, the compound of the present invention may be used as the light emitting layer 150 and / or the electron transporting layer 160 material.

On the other hand, since the band gap, the electrical characteristics, the interface characteristics, and the like can be changed depending on which substituent is bonded at any position even in the same core, the selection of the core and the combination of the sub- Especially when the optimum combination of energy level and T1 value between the organic layers, intrinsic properties (mobility, interface characteristics, etc.) of the materials are achieved, long lifetime and high efficiency can be achieved at the same time.

Therefore, by forming the light emitting layer and the electron transporting layer by using the compound of the present invention, it is possible to optimize the energy level and T1 value between the respective organic layers, the mobility of the material, and the interface characteristics, Efficiency can be improved at the same time.

In order to solve the problem of light emission in the hole transporting layer in recent organic electroluminescent devices, it is preferable that a light emitting auxiliary layer is formed between the hole transporting layer and the light emitting layer, and the light emitting layers (R, G and B) It is time to develop an auxiliary layer. On the other hand, in the case of the light-emission-assisting layer, it is difficult to deduce the characteristics of the organic layer to be used even if a similar core is used because the relationship between the hole-transport layer and the light-emitting layer (host)

An organic electroluminescent device according to an embodiment of the present invention may 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, And may be manufactured in a smaller number of layers by a dipping process, a screen printing process, a thermal transfer process, or the like. 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. 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, the compound according to one aspect of the present invention will be described.

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

≪ Formula 1 >

Wherein X ¹ , X ³ , X ⁵ and X ⁷ are N, X ² , X ⁴ , X ⁶ and X ⁸ are C or CR ^a , X ² and X ⁴ And at least one of X ⁶ and X ⁸ is CR ^a , and CR ^a to R ^a may be the same or different from each other. That is, R ^a are each independently of the others hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; And a C ₆ to C ₃₀ aryloxy group; For example, when X ² and X ⁶ are both CR ^a , R ^a of X ² may be hydrogen and R ^a of X ⁶ may be phenyl.

In Formula 1, R ¹ and R ² are independently selected from the group consisting of 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; And an aryloxy group having from ₆ to ₃₀ carbon atoms. For example, R ¹ and R ² can be, independently of each other, phenyl, biphenyl, triphenyl, naphthyl, phenanthrene, triphenylene, and the like.

In Formula (1), m and n are each an integer of 0 to 4. In this case, when m and n are 0, it means that hydrogen is bonded to the carbon of the benzene ring or L is connected to the benzene ring.

이다. 여기서, R^b 및 R^c는 서로 독립적으로, 수소; C₆~C₆₀의 아릴기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C₂~C₆₀의 헤테로고리기; C₁~C₅₀의 알킬기; C₂~C₂₀의 알켄일기; C₁~C₃₀의 알콕시기; 및 플루오렌일기;로 이루어진 군에서 선택되거나, 또는 R^b 및 R^c가 서로 결합하여 이들이 결합된 플루오렌과 함께 스파이로 화합물을 형성할 수 있다.In the above formula (1), L represents an unsubstituted C ₆ -C ₆₀ arylene group or

to be. Wherein R ^b and R ^c are independently from each other hydrogen; 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 C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxy group; And a fluorenyl group; or R ^b and R ^c may be bonded to each other to form a spiro compound together with the fluorene to which they are bonded.

The linking group L is bonded when one of X ² and X ⁴ is C or one of X ⁶ and X ⁸ is C, and when both of X ² , X ⁴ , X ⁶ and X ⁸ are CR ^a , the carbon of the benzene ring Lt; / RTI > That is, when X ² , X ⁴ , X ^6, and X ⁸ are both CR ^a , linking group L bonds to one of the carbons of the benzene ring to which R ¹ and R ² are bonded. Thus, m and n may be integers from 0 to 3 at this time.

When L is a fluorenylene group or an unsubstituted arylene group, the device characteristics can be improved since L exhibits relatively higher thermal stability and electron mobility than that of substituted arylene.

On the other hand, when R ^a , R ¹ and / or R ² is an aryl group, a fluorenyl group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group and / or an aryloxy group, halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; 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; Heterocyclic group of O, N, S, Si and C ₂ ~ containing at least one hetero atom in the P 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. For example, when R ¹ and R ² are aryl groups, each of these may be further substituted with one or more aryl such as phenyl, naphthyl, phenanthrene, triphenylene, and the like.

In addition, when R ¹ and / or R ² is a heterocyclic group and / or a fused ring group, each of them may be substituted with deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; 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; Heterocyclic group of O, N, S, Si and C ₂ ~ containing at least one hetero atom in the P 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.

When L is an arylene group, it may be selected from the following group.

Specifically, the formula (1) may be represented as follows. Provided that when R is represented by the following formula, R is the above-described R ^a or a single bond, and when it is a single bond,

In the above formula (1), X ² and X ⁴ One of the X ⁶ and X ⁸ of the case C and to the remainder is ^a CR can be represented by the following formula 1-1. That is, L is the sum of X ² and X ⁴ Because of the coupling and at the same time as the C coupled as the X ⁶ and X ⁸ of the C, the linking group L is bonded to N includes ring.

≪ Formula 1-1 >

In Formula 1-1, X ¹ to X ⁸ , L, R ¹ , R ² , m, and n are the same as defined in Formula 1.

Illustratively, the formula (1) may be represented by one of the following formulas (2) to (4).

X ² , X ⁴ , X ⁶ and X ⁸ are CR ^a and L, R ¹ , R ² , m and n are the same as defined in the formula (1).

Specifically, the compound according to the present invention may be one of the following compounds.

Hereinafter, synthesis examples of the compounds according to the present invention will be described. The following synthesis method is merely an example for synthesizing the compound of the present invention, and the scope of the present invention is not limited thereto.

[ Synthetic example ]

Illustratively, the compounds according to the present invention (Final Product: Product A-1 to C-230) may be prepared by the reaction shown in Reaction Scheme 1 below.

<Reaction Scheme 1>

(Wherein X ¹ to X ⁸ , L, R ¹ , R ² , m and n are the same as defined in formula (1)

I. Sub  Synthesis of 1

Sub 1 of Scheme 1 may be synthesized by the reaction pathway of Scheme 2, but is not limited thereto.

<Reaction Scheme 2>

Specific examples of the compound belonging to Sub 1 are as follows.

One. Sub  1-1 Synthetic example

<Reaction Scheme 3>

The starting material, 2-chloro-4-phenylquinazoline (7.3 g, 30.3 mmol) was dissolved in 100 ml of THF in a round bottom flask and then 1,4-bis (4,4,5,5-tetramethyl- dioxaborolan-2-yl) benzene (10.0 g, 30.3 mmol), Pd (PPh ₃ ) ₄ (1.4 g, 1.2 mmol), K ₂ CO ₃ (12.6 g, 90.9 mmol) Lt; / RTI &gt; After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 9.3 g (yield: 75%) of the product.

2. Sub  1-7 Synthetic example

<Reaction Scheme 4>

To a solution of 1,4-bis (4,4,5,5-tetramethyl-1,3- (1,1'-biphenyl) -3-yl) -2-chloroquinazoline (9.6 g, 30.3 mmol) 2-dioxaborolan-2-yl) benzene (10 g, 30.3 mmol), Pd (PPh ₃ ) ₄ (1.4 g, 1.2 mmol), K ₂ CO ₃ (12.6 g, 90.9 mmol) 9.5 g (Yield: 65%) of the product was obtained using the Sub 1-1 synthesis method.

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

[Table 1]

Hereinafter, a method for synthesizing the compound according to the present invention using Sub 1 will be described as an example.

II . The final product ( Final Product ) Synthesis of

(1.2 당량), Pd(PPh₃)₄(0.05 당량), K₂CO₃ (3 당량), 물을 첨가하고 95°C에서 교반하였다. 반응이 완료되면 CH₂Cl₂와 물로 추출한 후 유기층을 MgSO₄로 건조하고 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 Final products를 얻었다.
Sub 1 (1 eq.) Was dissolved in toluene in a round bottom flask,

(1.2 eq.), Pd (PPh ₃ ) ₄ (0.05 eq.), K ₂ CO ₃ (3 eq.), Water and stirred at 95 ° C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain final products.

One. Product  A-1 Synthetic example

<Reaction Scheme 5>

Obtained in the above Synthesis Sub 1-1 (4.4g, 10.8mmol) was dissolved in Toluene 40ml round bottom flask, 2-chloro-4-phenylquinazoline (2.6g, 10.8mmol), Pd (PPh 3) 4 (0.5g , 0.4 mmol of K ₂ CO ₃ , 32.7 mmol) and 20 ml of water were added and stirred at 95 ° C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 4.5 g (yield: 85%) of the product.

2. Product  A-7 Synthetic example

<Reaction Scheme 6>

Sub 1-7 obtained in the above Synthesis (5.3g, 10.8mmol) in 4 - ([1,1'-biphenyl] -3-yl) -2-chloroquinazoline (3.4g, 10.8mmol), Pd (PPh 3) 4 4.5 g (Yield: 65%) of the product was obtained by using the above A-1 synthesis method using 0.5 g (0.4 mmol) of K ₂ CO ₃ (4.5 g, 32.7 mmol), 40 ml of toluene and 50 ml of water.

3. Product  B-1 Synthetic example

<Reaction Scheme 7>

4-chloro-2-phenylquinazoline (2.6 g, 10.8 mmol), Pd (PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and K ₂ CO ₃ 4.5 g, 32.7 mmol), 40 ml of toluene and 20 ml of water were obtained 4.3 g (yield: 82%) of the product using the A-1 synthesis method described above.

4. Product  B-7 Synthetic example

<Reaction Scheme 8>

Sub 2-7 obtained in the above Synthesis (5.3g, 10.8mmol) in 2 - ([1,1'-biphenyl] -3-yl) -4-chloroquinazoline (3.4g, 10.8mmol), Pd (PPh 3) 4 4.1 g (yield: 60%) of the product was obtained using the above A-1 synthesis method, and the product (0.5 g, 0.4 mmol), K ₂ CO ₃ (4.5 g, 32.7 mmol), Toluene 40 ml and water 50 ml.

5. Product  C-1 Synthetic example

<Reaction Scheme 9>

2-chloro-4-phenylquinazoline (2.6 g, 10.8 mmol), Pd (PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and K ₂ CO ₃ 4.5 g, 32.7 mmol), 40 ml of toluene and 20 ml of water were used to obtain 3.9 g (yield: 75%) of the product using the A-1 synthesis method described above.

6. Product  C-7 Synthetic example

<Reaction formula 10>

Sub 1-7 obtained in the above Synthesis (5.3g, 10.8mmol) in 2 - ([1,1'-biphenyl] -3-yl) -4-chloroquinazoline (3.4g, 10.8mmol), Pd (PPh 3) 4 3.8 g (Yield: 55%) of the product was obtained using the above A-1 synthesis method, and the product (0.5 g, 0.4 mmol), K ₂ CO ₃ (4.5 g, 32.7 mmol), Toluene 40 ml and water 50 ml.

In the meantime, although the exemplary synthesis examples of the present invention represented by the general formula (1) have been described above, they are all based on the Miyaura boration reaction and the Suzuki cross-coupling reaction. In addition to the substituents specified in the specific synthesis example, ¹ to ^{X 8, L, R 1,} R 2 , etc. of the substituent) are even combined by those skilled in the art will be easily understood that the reaction proceeds. For example, in the reaction scheme 2, the starting material -> Sub 1 reaction is based on the Miyaura boration reaction, and the reaction schemes 5 to 10 are based on the Suzuki cross-coupling reaction. Even if substituents not specifically mentioned in these groups are bonded, the reactions will proceed.

FD-MS values of the compounds A-1 to A-214, B-1 to B-215 and C-1 to C-230 of the present invention prepared according to the above Synthesis Example are shown in Table 2.

[Table 2]

Examples 1 to 659 in which the compound according to the present invention is applied to an organic electric device to measure device characteristics will be described below.

Evaluation of manufacturing of organic electric device

[ Example  1] Green organic electroluminescent device ( Electron transport layer )

Organic electroluminescent devices were fabricated according to a conventional method using the compounds of the present invention as electron transport layer materials.

First, 4,4 ', 4 "-tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter abbreviated as 2-TNATA) was vacuum deposited on the ITO layer (anode) After the hole injection layer was formed, 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter referred to as NPD) was vacuum deposited on the hole injection layer to a thickness of 60 nm, . Next, CBP [4,4'-N, N'-dicarbazole-biphenyl] was used as a host material and Ir (ppy) ₃ [tris (2-phenylpyridine) -iridium] 5 by weight to form a light emitting layer having a thickness of 30 nm. Subsequently, aluminum (1,1'bisphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited on the light emitting layer to a thickness of 10 nm, Layer, and the compound A-1 of the present invention was vacuum deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer. Thereafter, LiF, which is 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.

[ Example  2] to [ Example  659] green organic electroluminescent device Electron transport layer )

Except that the compounds A-2 to A-214, B-1 to B-215 and C-1 to C-230 of the present invention shown in the following Table 3 were used as the electron transport layer material instead of the compound A- , An organic electroluminescent device was fabricated in the same manner as in Example 1.

[ Comparative Example  One]

An organic electroluminescence device was fabricated in the same manner as in Example 1, except that Comparative Compound 1 was used instead of Compound A-1 of the present invention as an electron transport layer material.

&Lt; Comparative Compound 1 > Alq ₃

[ Comparative Example  2]

An organic electroluminescence device was prepared in the same manner as in Example 1 except that Comparative Compound 2 was used instead of Compound A-1 of the present invention as an electron transport layer material.

&Lt; Comparative Compound 2 >

[ Comparative Example  3]

An organic electroluminescent device was fabricated in the same manner as in Example 1 except that Comparative Compound 3 was used instead of Compound A-1 of the present invention as an electron transport layer material.

&Lt; Comparative Example 3 >

[ Comparative Example  4]

An organic electroluminescence device was prepared in the same manner as in Example 1, except that Comparative Compound 4 was used instead of Compound A-1 of the present invention as an electron transport layer material.

<Comparative Compound 4>

[ Comparative Example  5]

An organic electroluminescence device was fabricated in the same manner as in Example 1, except that Comparative Compound 5 was used instead of Compound A-1 of the present invention as an electron transport layer material.

&Lt; Comparative Compound 5 >

[ Comparative Example  6]

An organic electroluminescence device was fabricated in the same manner as in Example 1, except that Comparative Compound 6 was used instead of Compound A-1 of the present invention as an electron transport layer material.

&Lt; Comparative Compound 6 >

[ Comparative Example  7]

An organic electroluminescent device was fabricated in the same manner as in Example 1, except that Comparative Compound 7 was used instead of Compound A-1 of the present invention as an electron transport layer material.

<Comparative Compound 7>

Electruminescence (EL) characteristics were measured with photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 1 to 659 and Comparative Examples 1 to 7 of the present invention And the T95 lifetime was measured by a life measuring device manufactured by Mac Science Inc. at a reference luminance of 5000 cd / m ² . The results are shown in Table 3 below.

[Table 3]

As can be seen from the results of the above [Table 3], the organic electroluminescent device used as the material of the electron transport layer of the compound of the present invention has a higher driving voltage than the organic electroluminescent device using Comparative Compounds 1 to 7 as the material of the electron transport layer And the luminous efficiency was improved, as well as the lifetime and the like were remarkably improved.

This is of use as a dopant in the light emitting layer Ir (ppy) Comparative compound used as the electron transport layer than the T ₁ value (2.4 eV) of ₃ 1 (Alq ₃₎ to Comparative Compound 4 T ₁ value (2.0 eV) have a significantly lower T ₁ value represent, while the case of the compounds of the present invention, Ir (ppy) ₃ of the T ₁ value (2.4 eV) than the generally exhibits a high T ₁ value (2.5 ev ~ 2.6 ev) to stay in the light emitting layer well exciton (exciton) This is because the probability is relatively increased.

In addition, even with the same bis type quinazoline core, the compound of the present invention, which is unsubstituted in comparison with Compounds 5 to 7 in which the alkyl group is substituted at the linking group L, exhibits more excellent device results, The compound of the present invention having the linking group L has relatively higher thermal stability and electron mobility than the compound having the substituted L so that the hole and electron have a charge balance in the light emitting layer, It is possible to realize the optimal light emitting efficiency through the light emitting diode.

Taken together, the above-described characteristics (high T1 value, fast electron mobility and high thermal stability) indicate that the band gap, electrical characteristics, and interface characteristics of the bis type quinazoline core And it can be confirmed that this is a major factor in improving the performance of the device.

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

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

Claims (11)

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

[In the formula,
X ¹ , X ³ , X ⁵ and X ⁷ are N, X ² , X ⁴ , X ⁶ and X ⁸ are C or CR ^a , X ² and X ⁴ And at least one of X &lt; ⁶ &gt; and X &lt; ⁸ &gt; is CR &^lt; ^a &
R ^a independently from each other are hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; And a C ₆ to C ₃₀ aryloxy group; , &Lt; / RTI &gt;
L is an unsubstituted C ₆ to C ₆₀ arylene group or

Wherein R ^b and R ^c are independently of each other 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; ; C ₁ ~ alkyl group of C _50; C ₂ ~ of the C ₂₀ alkenyl group; an alkoxy group of C ₁ ~ C _30; and a fluorenyl group; or selected from the group consisting of, or R ^b and R ^c are combined to which they together Together with the fused fluorene, form a spiro compound),
R ¹ and R ² 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; And an aryloxy group of C ₆ to C ₃₀ ; m and n are each an integer of 0 to 4,
Wherein R ^a, R ¹ and R ² of the aryl group, fluorene group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group, a heterocyclic group of R ¹ and R ^2, and a fused ring group each of which heavy hydrogen; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; 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; Heterocyclic group of O, N, S, Si and C ₂ ~ containing at least one hetero atom in the P 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. The method according to claim 1,
Lt; RTI ID = 0.0 &gt; 1, &lt; / RTI &gt;

Wherein X ² , X ⁴ , X ⁶ and X ⁸ are CR ^a and L, R ¹ , R ² , m and n are the same as defined in claim 1, The method according to claim 1,
When L is an unsubstituted arylene group, the compound is selected from the following group.

The method according to claim 1,
Lt; / RTI &gt; is one of the following compounds.

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 contains the compound of any one of claims 1 to 4. 6. The method of claim 5,
Wherein the organic layer includes a light emitting layer and an electron transporting layer,
Wherein the compound is contained in at least one of the light emitting layer and the electron transporting layer. 6. The method of claim 5,
Wherein the organic layer further comprises a light emitting layer and a light emitting auxiliary layer formed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode. 6. The method of claim 5,
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. 6. The method of claim 5,
Wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process. A display device comprising the organic electroluminescent device of claim 5; And
And a control unit for driving the display device. 11. The method of claim 10,
Wherein the organic electroluminescent device is 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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