KR20190087143A - Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof - Google Patents

Abstract

Disclosed are an organic electronic element comprising: a compound represented by chemical formula 1; a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, and an electronic device comprising the organic electronic element. By comprising the compound represented by chemical formula 1 in the organic layer, it is possible to lower a driving voltage, improve luminous efficiency, and expand lifespan of the organic electronic element.

Description

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

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

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

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

Currently, the portable display market is increasing in size as a large-area display, which requires more power than the power consumption required by existing portable displays. Therefore, power consumption is an important factor for portable displays, which have a limited power source, such as a battery, and efficiency and longevity are also important factors to be solved.

The efficiency, lifetime, and driving voltage are related to each other. As the efficiency increases, the driving voltage drops and the driving voltage drops. As a result, crystallization of the organic material due to Joule heating, which occurs during driving, And the lifetime tends to increase. However, simply improving the organic material layer can not maximize the efficiency. This is because, when the optimal combination of the energy level and T1 value between each organic material layer and the intrinsic properties (mobility, interface characteristics, etc.) of the material are achieved, long life and high efficiency can be achieved at the same time.

In recent organic EL devices, in order to solve the emission problem and the driving voltage problem in the hole transport layer, a light emission auxiliary layer (multilayer hole transport layer) must exist between the hole transport layer and the light emitting layer, It is necessary to develop a light-emitting auxiliary layer.

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 recombine electrons and holes in the light emitting layer to form excitons.

However, the material used for the hole transport layer has a low HOMO value and therefore has a low T 1 value. As a result, the exciton generated in the light emitting layer is transferred to the hole transport layer, resulting in a charge unbalance in the light emitting layer. And emits light at the interface of the hole transporting layer.

When light is emitted from the interface of the hole transporting layer, the color purity and efficiency of the organic electronic device are lowered and the lifetime is shortened. Therefore, the material should have a HOMO energy level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer, and have a high T1 value and a hole mobility of within a suitable driving voltage range it is urgently required to develop a light-emitting auxiliary layer material having hole mobility.

However, this can not be achieved simply by the structural characteristics of the core of the light-emitting auxiliary layer material, and when the proper combination of the characteristics of the core and the sub-substituent of the light-emitting auxiliary layer material and the light emitting auxiliary layer, the hole transport layer, High efficiency and high number of devices can be realized.

In order to sufficiently exhibit the excellent characteristics of the organic electronic device, a material forming the organic material layer in the device, for example, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, And particularly the development of materials for the light emitting auxiliary layer is urgently required.

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

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

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

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

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

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

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

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

The term "heterocyclic group" used in the present invention means a ring containing a hetero atom such as N, O, S, P or Si instead of carbon forming a ring, and the term "heteroaryl group" or "heteroarylene group" As well as non-aromatic rings, and compounds containing hetero atoms such as SO ₂ , P═O, etc., such as the following compounds, instead of ring-forming carbon, may also be included.

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 shown below, and wherein R ¹ may be the same or different from each other, a is and bonded to the carbon of the benzene ring in the similar manner in this case from 4 to 6 integer, while the display of the hydrogen bonded to the carbon to form a benzene ring It is omitted.

Hereinafter, a lamination structure of an organic electronic device including a compound of the present invention will be described with reference to FIG.

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

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

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

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

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

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

Accordingly, in the present invention, by forming the emission auxiliary layer 151 using the compound represented by the general formula (1), the energy level and T ₁ value between each organic material layer, the intrinsic properties (mobility, interface characteristics, etc.) It is possible to simultaneously improve the lifetime and efficiency of the electric element.

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

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

The organic electroluminescent device according to the present invention can be one of an organic electroluminescent (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device, or a device for a quantum dot display.

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. At this time, 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, The display device may include an organic electroluminescent display, a quantum dot display, and the like.

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 >

Ar ¹ to Ar ⁴ independently represent 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 ; And at least one of Ar ¹ to Ar ⁴ is represented by the following general formula (1-1).

≪ Formula 1-1 >

When Ar ¹ to Ar ⁴ are aryl groups, it is preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₁₈ aryl group such as phenyl, biphenyl, naphthyl, phenanthrene, triphenyl Lt; / RTI > can be, for example, When Ar ¹ to Ar ⁴ are heterocyclic groups, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₂ heterocyclic group such as dibenzothiophene, dibenzofuran, Sol, phenylcarbazole, 9- (naphthalen-2-yl) -9H-carbazole, benzonaphthothiophene, benzonaphthofuran and the like.

X and Y are S or O.

R ¹ to R ⁴ independently of one another are hydrogen; heavy hydrogen; halogen; Cyano; A nitro group; 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 ₃ to C ₆₀ aliphatic ring; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And -L'-N (R _a ) (R _b ); adjacent groups may combine with each other to form a ring, wherein the ring is a C ₆ to C ₆₀ aromatic ring; A fluorenyl group; _{O, N, S, C 2} ~ C ₆₀ heteroaryl rings containing Si and P, at least one of the hetero atoms in the; A C ₃ to C ₆₀ aliphatic ring; And combinations thereof.

When R ¹ to R ⁴ are heterocyclic groups, it is preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₂ heterocyclic group such as dibenzothiophene, dibenzofurane, etc. have.

l is from 0 to 3 an integer, n, m, o is an integer from 0 to 4, are different from each of these cases, each integer equal to or greater than two, and each R ^1, each R ^2, each R ³ and each R ⁴ The same or different.

L 'is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And fused ring groups of the aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; may be selected from the group consisting of.

R _a and R _b are independently of each other 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; And fused ring groups of the aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; may be selected from the group consisting of.

The ^{Ar 1 -Ar 4, R 1 -R} 4, adjacent to each other R ^1, R ² adjacent to each other, adjacent to each other R ^3, R ⁴ adjacent the ring formed by combining each other, L ', R _a and R _b is deuterium; halogen; A silane group substituted or unsubstituted with an alkyl group having _{1 to 20} carbon atoms or an aryl group having _{6 to 20} carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; A phosphine oxide group substituted or unsubstituted with an alkyl group having _{1 to 20} carbon atoms or an aryl group having _{6 to 20} carbon atoms; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; Aryl alkenyl group of C ₈ -C _20; -L ' -N (R ' _a ) (R ' _b ); And a combination of these.

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

&Lt; Formula 2 > < EMI ID =

R ¹ , R ² , Ar ¹ -Ar ⁴ , X, m and n are as defined in formula (1).

The formula (1) may be represented by one of the following formulas (5) to (9).

&Lt; Formula 5 > < EMI ID =

(8) &Lt; Formula 9 >

R ¹ -R ⁴ , Ar ¹ -Ar ⁴ , X, Y, m, n, l and o are as defined in formula (1).

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

.

.

According to another embodiment of the present invention, there is provided an organic electronic device including a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, Species alone compound or two or more compounds.

The organic compound layer includes at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary charge, an electron transporting layer, and an electron injection layer. Preferably, the compound is included in the light emitting auxiliary layer or the hole transporting layer. do.

In another embodiment of the present invention, there is provided an electronic device including a display device including the organic electroluminescent device and a control unit for driving the display device.

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

Synthetic example

The compound represented by Formula 1 according to the present invention can be prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below.

Reaction formula 1 (X = S or O)

Sub 1's Synthetic example

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

<Reaction Scheme 2>

Examples of the synthesis of compounds belonging to Sub 1 are as follows.

Sub 1-4 of Synthetic example

3-amine (9.7 g, 37.4 mol), Pd ₂ (dba) ₃ (0.68 g, 37.4 mmol), N-phenyldibenzo [b, d] furan- 0.75 mmol), P ( t- Bu) ₃ (0.30 g, 1.5 mmol) and NaO t- Bu (7.2 g, 74.8 mmol) were dissolved in toluene and stirred at 65 ° C for 4 hours. When the reaction is complete, add distilled water at room temperature to extract. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was passed through a silica gel column and then recrystallized to obtain Sub 1-4 (14.5 g, 81%).

Sub 1-5's Synthetic example

(5.64 g, 33.8 mol), Pd ₂ (dba) ₃ (0.61 g, 0.67 mmol), P ( t- Bu) ₃ (4-bromophenyl) (3- chlorophenyl) sulfane 0.25 g, 1.3 mmol) and NaO t- Bu (6.4 g, 66.8 mmol), Sub 1-5 (10.4 g, 80%) was obtained in the same manner as in the synthesis of Sub 1-4 above.

Sub 1-25 Synthetic example

Phenyl dibenzo [b, d] furan-3-amine (10.1 g, 39.0 mol), Pd ₂ (dba) ₃ (0.7 g, 39.0 mmol) and 1-bromo-3- (3- chlorophenoxy) benzene Sub 15-2 (15.5) was obtained in the same manner as in the synthesis of Sub 1-4 using the above-mentioned synthesis of Sub 1-4 by using 0.8 g (0.8 mmol) of P ( t- Bu) ₃ (0.32 g, 1.56 mmol) and NaO t- g, 86%).

Sub 1-44 of Synthetic example

Pd ₂ (dba) ₃ (1.67 g, 1.8 mmol), P ((4-bromophenoxy) -3-chlorobenzene (21.8 g, 91.4 mol), N-phenyltriphenylen- _{t -Bu) 3 (0.74 g,} 3.7 mmol), NaO t -Bu (17.6 g, 182.8 mmol) to use to obtain the Sub 1-44 (40.6g, 85%) in the same manner as in the synthesis method of the Sub1-4 .

Sub 1-48 of Synthetic example

(13.2 g, 47.8 mol), Pd ₂ (dba) ₃ (0.9 g, 47.8 mmol), N-phenyldibenzo [b, d] thiophen- (17.6 g, 100 mmol) was obtained in the same manner as in the synthesis of Sub1-4 using P ( t- Bu) ₃ (0.4 g, 2.0 mmol) and NaO t- g, 77%).

The compound belonging to Sub 1 may be, but not limited to, the FD-MS values for the following compounds are shown in Table 1.

[Table 1]

Sub 2 Synthetic example

Sub 2 of Reaction Scheme 1 can be synthesized by the reaction path of the following Reaction Scheme 3, but is not limited thereto.

(Z ¹ = Ar ¹ or Ar ³ , and Z ² is Ar ² or Ar ⁴ )

A specific method for synthesizing a compound belonging to Sub 2 was the method disclosed in Korean Patent No. 10-1251451 (registered on March 31, 2013).

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

[Table 2]

Of the final compound Synthetic example

P-4 Synthetic Example

Sub 1-4 (11.4 g, 23.8 mol ), Sub 2-13 (4.0 g, 23.8 mol), Pd 2 (dba) 3 (0.44 g, 0.5 mmol), P (t -Bu) 3 (0.2 g, 1.0 mmol) and NaO t- Bu (4.6 g, 48.0 mol) are dissolved in toluene and refluxed at 120 ° C. When the reaction is complete, add distilled water at room temperature to extract. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was passed through a silica gel column and then recrystallized to obtain final compound P-4 (12.4 g, yield: 85%).

Example of P-19 synthesis

Sub 1-7 (13.0 g, 23.3 mol ), Sub 2-13 (3.8 g, 23.3 mol), Pd 2 (dba) 3 (0.4 g, 0.4 mmol), P (t -Bu) 3 (0.2 g, 0.9 The final compound P-19 (13.9 g, yield: 87%) was obtained in the same manner as in the synthesis of P-4 using NaO t- Bu (4.3 g, 44.5 mol).

Example of P-22 synthesis

Sub 1-5 (12.2 g, 31.4 mol ), Sub 2-14 (13.9 g, 31.4 mol), Pd 2 (dba) 3 (0.6 g, 0.6 mmol), P (t -Bu) 3 (0.25 g, 1.26 (22.7 g, yield: 91%) was obtained in the same manner as in the synthesis of P-4 described above, using NaO t- Bu (6.0 g, 62.9 mol)

P-33 Synthetic Example

Sub 1-5 (9.8 g, 25.3 mol ), Sub 2-21 (8.9 g, 25.3 mol), Pd 2 (dba) 3 (0.46 g, 0.51 mmol), P (t -Bu) 3 (0.2 g, 1.0 mmol) and NaO t- Bu (4.9 g, 50.5 mol), the final compound P-33 (15.6 g, yield: 88%) was obtained in the same manner as in the synthesis of P-4.

Example of P-51 synthesis

Sub 1-6 (12.3 g, 26.5 mol ), Sub 2-23 (8.9 g, 26.5 mol), Pd 2 (dba) 3 (0.49 g, 0.53 mmol), P (t -Bu) 3 (0.2 g, 1.0 mmol) and NaO t- Bu (5.1 g, 53.0 mol), the final compound P-51 (17.8 g, yield: 88%) was obtained in the same manner as in the synthesis of P-4.

Example of P-69 synthesis

Sub 1-43 (14.0 g, 28.3 mol ), Sub 2-13 (4.8 g, 28.3 mol), Pd 2 (dba) 3 (0.52 g, 0.57 mmol), P (t -Bu) 3 (0.23 g, 1.1 mmol) and NaO t- Bu (5.4 g, 57.0 mol), the final compound P-69 (15.8 g, yield: 89%) was obtained in the same manner as in the synthesis of P-4.

Example of P-92 synthesis

Sub 1-60 (13.0 g, 35.0 mol ), Sub 2-6 (12.3 g, 35.0 mol), Pd 2 (dba) 3 (0.64 g, 0.7 mmol), P (t -Bu) 3 (0.28 g, 1.4 The final compound P-92 (19.0 g, yield: 79%) was obtained in the same manner as in the synthesis of P-4 above, using NaO t- Bu (6.7 g, 70.0 mol).

Example of P-98 synthesis

Sub 1-39 (13.0 g, 23.5 mol ), Sub 2-6 (4.0 g, 23.5 mol), Pd 2 (dba) 3 (0.43 g, 0.47 mmol), P (t -Bu) 3 (0.20 g, 1.0 The final compound P-98 (14.7 g, yield: 91%) was obtained in the same manner as in the synthesis of P-4 above, using NaO t- Bu (4.5 g, 47.0 mol).

The FD-MS values of the compounds P-1 to P-104 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[Table 3]

Evaluation of manufacturing of organic electric device

[ Example  One] Red organic electroluminescent device  ( The light- )

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 N-bis (1-naphthalenyl) -N, N (N-bis-Naphthalenyl) -N-phenylbenzene-1,4-diamine (hereinafter abbreviated as 2-TNATA) '-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine (hereinafter abbreviated as "NPB") was vacuum deposited to a thickness of 60 nm to form a hole transport layer.

Next, Compound P-1 of the present invention was vacuum deposited on the hole transport layer to a thickness of 20 nm to form a light-emission-assisting layer, and 4,4'-N, N'- (1-phenylisoquinolyl) iridium (III) acetylacetonate (hereinafter referred to as "(piq) ₂ Ir (acac)") as a dopant material was used as a dopant material. Thereby forming a light emitting layer having a thickness of 30 nm in a weight ratio.

Next, (1,1'-biphenyl-4-olato) bis (2-methyl-8-quinolinolato) aluminum (abbreviated as "BAlq" hereinafter) was vacuum deposited on the light emitting layer to a thickness of 5 nm to form a hole blocking layer And a layer of 40 nm thick Bis (10-hydroxybenzo [h] quinolinato) beryllium (abbreviated as "BeBq ₂ " hereinafter) was formed on the hole blocking layer to form an electron transporting layer.

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

[ Example  2] to [ Example  42]

An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compounds P-2 to P-104 of the present invention described in Table 4 were used instead of the compound P-1 of the present invention as the luminescent auxiliary layer material .

[ Comparative Example  One]

An organic electroluminescence device was fabricated in the same manner as in Example 1 except that no luminescent auxiliary layer was formed.

[ Comparative Example  2] to [ Comparative Example  4]

An organic electroluminescence device was fabricated in the same manner as in Example 1, except that one of Comparative Compounds A to C was used in place of Compound P-1 of the present invention as a luminescent auxiliary layer material.

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

Electroluminescence (EL) characteristics were measured by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices of Examples 1 to 42 and Comparative Examples 1 to 4 thus prepared , And the T95 lifetime was measured through a life measurement device manufactured by Mac Science Inc. at a reference luminance of 2500 cd / m ² as a result of the measurement. Table 4 shows the measurement results.

[Table 4]

As can be seen from the results in Table 4, when the red organic electroluminescent device was manufactured using the organic electroluminescent device material of the present invention as the light emitting auxiliary layer material, the light emitting auxiliary layer was not formed, C, the driving voltage of the organic electroluminescent device can be lowered, as well as the luminous efficiency and lifetime can be remarkably improved.

The device results of Comparative Examples 2 to 4 in which the light emitting auxiliary layer was formed using Comparative Compounds A to C were superior to those of Comparative Example 1 in which the light emitting auxiliary layer was not formed, But the device results of Examples 1 to 42 in which the light-emitting auxiliary layer was formed using the compound of the present invention in which specific substituents such as dibenzothiophene or dibenzofurane were bonded to the amine group were remarkably excellent.

Comparing the comparative compound A with the comparative compound B, there is a difference only in whether the amine group bonded to the diphenyl sulfane moiety is bonded to the meta position or to the para position, and the comparative compound B The device results were better. This is because the energy level (especially, the HOMO level) is changed when the bonding position of the amine group is changed, and this property difference is a major factor in improving the device performance in depositing the compound in the device manufacturing, see.

Similarly, when comparing Comparative Compound B and Comparative Compound C with the compound of the present invention, it is the same that the S portion or the O portion bonded to the phenyl and the amine group are bonded at the meta position, but Comparative Compounds B and C are the same as the amine group Are all substituted with phenyl, the compounds of the present invention are different in that at least one dibenzothiophene or dibenzofuran is substituted for the amine group, and when the compound of the present invention is used as a light emitting auxiliary layer material The device characteristics were remarkably improved. From these results, it can be seen that the type of the substituent group to be substituted for the amine group varies, and the device characteristics can also be changed.

When dibenzothiophene or dibenzofurane is introduced as a substituent, the refractive index is significantly higher than that of a general aryl group, and Tg is also increased, thereby improving thermal stability. Therefore, when the compound according to the present invention is used as the light-emitting auxiliary layer material, the device characteristics are considered to be improved.

In conclusion, amine groups are bonded to both phenyl groups of a diphenylsulfane or diphenylether core, and at least one of them is necessarily bonded to the meta position with S or O, It can be confirmed that the compound of the present invention having a benzothiophene or dibenzofurane as a substituent shows remarkably excellent performance compared with the similar compounds.

In the evaluation results of the device fabrication described above, the device characteristics of the present invention in which the compound of the present invention is applied only to the light emitting auxiliary layer has been described. However, the compound of the present invention may be used in the hole transporting layer or in both the hole transporting layer and the light emitting supporting layer.

The foregoing description is merely illustrative of the present invention, and various modifications may be made without departing from the essential characteristics of the present invention. 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 claims 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 (10)

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

Ar ¹ to Ar ⁴ independently represent 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 ; And at least one of Ar ¹ to Ar ⁴ is selected from the group consisting of:
&Lt; Formula 1-1 >

X and Y are S or O,
R ¹ to R ⁴ independently of one another are hydrogen; heavy hydrogen; halogen; Cyano; A nitro group; 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 ₃ to C ₆₀ aliphatic ring; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And -L'-N (R _a ) (R _b ); adjacent groups may combine with each other to form a ring, wherein the ring is a C ₆ to C ₆₀ aromatic ring; A fluorenyl group; _{O, N, S, C 2} ~ C ₆₀ heteroaryl rings containing Si and P, at least one of the hetero atoms in the; A C ₃ to C ₆₀ aliphatic ring; And combinations thereof,
l is from 0 to 3 an integer, n, m, o is an integer from 0 to 4, are different from each of these cases, each integer equal to or greater than two, and each R ^1, each R ^2, each R ³ and each R ⁴ The same or different,
L 'is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And C ₃ ~ fused ring group of an aromatic ring of C ₆₀ of aliphatic rings and C ₆ ~ C _60; is selected from the group consisting of,
R _a and R _b are independently of each other 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; And C ₃ ~ fused ring group of an aromatic ring of C ₆₀ of aliphatic rings and C ₆ ~ C _60; is selected from the group consisting of,
The ^{Ar 1 -Ar 4, R 1 -R} 4, adjacent to each other R ^1, R ² adjacent to each other, adjacent to each other R ^3, R ⁴ adjacent the ring formed by combining each other, L ', R _a and R _b is deuterium; halogen; A silane group substituted or unsubstituted with an alkyl group having _{1 to 20} carbon atoms or an aryl group having _{6 to 20} carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; A phosphine oxide group substituted or unsubstituted with an alkyl group having _{1 to 20} carbon atoms or an aryl group having _{6 to 20} carbon atoms; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; Aryl alkenyl group of C ₈ -C _20; -L ' -N (R &apos; _a ) (R &apos; _b ); And a combination of these. The method according to claim 1,
(1) is represented by one of the following formulas (2) to (4):
&Lt; Formula 2 >< EMI ID =

Wherein R ¹ , R ² , Ar ¹ -Ar ⁴ , X, m and n are the same as defined in claim 1. The method according to claim 1,
(1) is represented by one of the following formulas (5) to (9):
&Lt; Formula 5 >< EMI ID =

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

R ¹ -R ⁴ , Ar ¹ -Ar ⁴ , X, Y, m, n, l and o are as defined in claim 1. The method according to claim 1,
Wherein the compound of formula (I) is one of the following compounds:

. A first electrode; A second electrode; And an organic material layer formed between the first electrode and the second electrode,
Wherein the organic material layer comprises a single species compound represented by the general formula (1) of claim 1 or two or more compounds. 6. The method of claim 5,
Wherein the organic material layer includes at least one of a hole injection layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer, and an electron injecting layer. The method according to claim 6,
Wherein the compound is contained in the hole transporting layer or the light emission-assisting 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. 10. The method of claim 9,
Wherein the organic electroluminescent device is selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, a monochromatic illumination device, and a quantum dot display device.

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