KR101249640B1 - Electroluminescent Polymers having 9-fluoren-2-yl-9-aryl-2,7-fluorenyl Unit and the Electroluminescent Device Prepared Using the Same - Google Patents

Abstract

The present invention relates to an electroluminescent molecule containing a 9-fluoren-2-yl-9-aryl-2,7-fluorenyl unit and an electroluminescent device using the same, wherein the substituted fluorenyl group is a 9-position of fluorene. Electroluminescent molecules containing 9-fluoren-2-yl-9-aryl-2,7-fluorenyl units, which can be used as blue electroluminescent polymers and host materials, and electroluminescent devices using the same. It is about.

The electroadhesive molecules according to the present invention can be used as host materials such as high purity blue, green and red having high solubility, high thermal stability and high quantum efficiency.

Light emitting polymer, light emitting device, blue light emitting, quantum efficiency, fluorene, fluorenyl

Description

Electroluminescent molecule containing 9-fluoren-2-yl-9-aryl-2,7-fluorenyl unit and electroluminescent device using same {Electroluminescent Polymers having 9-fluoren-2-yl-9-aryl-2,7 -fluorenyl Unit and the Electroluminescent Device Prepared Using the Same}

1 is a cross-sectional view showing a structure of a general organic electroluminescent device manufactured from a substrate / anode / hole transport layer / light emitting layer / electron transport layer / cathode.

2 is a cross-sectional view showing the structure of an electroluminescent device according to a preferred embodiment of the present invention.

3 is a cross-sectional view showing the structure of an electroluminescent device according to another preferred embodiment of the present invention.

Figure 4 is a reaction schematic showing the manufacturing process of the compound prepared according to Preparation Examples 1 to 3 of the present invention.

5 is a ¹ H-NMR spectrum of Compound (3) prepared according to Preparation Example 3 of the present invention.

FIG. 6 is a ¹ H-NMR spectrum of an electroadhesive molecule represented by Chemical Formula 2 of the present invention.

7 is an electroluminescent spectrum obtained from an electroluminescent device according to Example 4 of the present invention.

8 is an electroluminescent spectrum obtained from an electroluminescent device according to Example 6 of the present invention.

9 is a curve showing luminance according to voltage obtained from an electroluminescent device according to Example 5 of the present invention.

[Description of Reference Numerals]

11 substrate 12 anode

13 hole transport layer 14 light emitting layer

15: electron transport layer 16: cathode

17: PEDOT / PSS layer (500Å)

18: Electrophoresis molecule compound layer (100-2000 kPa) of the present invention

19: LiF (20Å)

20: Al (700Å)

21: Electro-molecular weight molecule compound layer of the present invention (100 ~ 2000Å)

22: Ca (500 Å)

23: Al (1,500Å)

The present invention relates to an electroluminescent molecule containing a 9-fluoren-2-yl-9-aryl-2,7-fluorenyl unit and an electroluminescent device using the same. More specifically, electro-molecules containing 9-fluoren-2-yl-9-aryl-2,7-fluorenyl unit having properties of excellent thermal stability, light stability, solubility, film formability and high quantum efficiency; It relates to an electroluminescent device using the same.

Recently, due to the rapid growth of the optical communication and multimedia fields, the development into a highly information society has been accelerated. Accordingly, optoelectronic devices using the conversion of photons to electrons or the conversion of electrons to photons have become the core of the modern information electronics industry.

Such semiconductor optoelectronic devices can be broadly classified into electroluminescent devices, light receiving devices, and devices in which they are combined.

Electroluminescence display, which is a self-luminous type, has a high response speed and self-emission type, so it does not need a backlight and has excellent brightness. Has attracted attention as a display device.

Such electroluminescent devices are classified into inorganic and organic light emitting devices according to materials for forming a light emitting layer.

Organic electroluminescence (EL) is a phenomenon in which when an electric field is applied to an organic material, electrons and holes are transferred from the cathode and the anode, respectively, to be combined within the material, and the energy generated is emitted as light. The electroluminescence phenomenon of such an organic material was reported by Pope et al. In 1963 and it was reported by Tang et al. In Eastmann Kodak in 1987 that alumina-quinone A light emitting device having a multi-layered structure having a quantum efficiency of 1% and a luminance of 1000 cd / m < 2 > at 10 V or less has been reported as an element fabricated from a dye having a pi-conjugated structure. They have the advantage of easy synthesis and synthesis of various types of materials and simple color tuning. However, when the processability and thermal stability are low and the voltage is applied, Joule heat is generated in the light emitting layer, and as the molecules are rearranged, the device is destroyed and causes problems in the luminous efficiency or life of the device. Substitution is proceeding with the organic electroluminescent device having.

In this regard, FIG. 1 shows a structure of a general electroluminescent device made of a substrate / anode / hole transport layer / light emitting layer / electron transport layer / cathode.

Referring to FIG. 1, an anode 12 is formed on the substrate 11. The hole transport layer 13, the light emitting layer 14, the electron transport layer 15, and the cathode 16 are sequentially formed on the anode 12. Here, the hole transport layer 13, the light emitting layer 14, and the electron transport layer 15 are organic thin films made of an organic compound. The driving principle of the electroluminescent device of the above structure is as follows:

When a voltage is applied between the anode 12 and the cathode 16, holes injected from the anode 12 are transferred to the light emitting layer 14 via the hole transport layer 13. On the other hand, electrons are injected into the light emitting layer 14 from the cathode 16 via the electron transport layer 15, and carriers are recombined in the light emitting layer 14 to generate excitons. This exciton is changed from the excited state to the ground state, whereby the fluorescent molecules of the light emitting layer emit light to form an image.

The electroluminescent device driven on the same principle is classified into a polymer organic electroluminescent device and a low molecular organic electroluminescent device according to the molecular weight of the material for forming an organic film.

In general, in the case of using a low molecule in forming the organic film, the low molecule is easy to purify and can almost eliminate impurities, and excellent in luminescence properties. However, there is a problem in that inkjet printing or spin coating is impossible and the heat resistance is poor, thereby deteriorating or recrystallizing by the driving heat generated when driving the device.

On the other hand, when the polymer is used to form the organic film, the energy level is separated into the conduction band and the electrical appliance diagram by the superposition of the π-electron wave function in the polymer backbone, and the band gap energy corresponding to the energy difference is used. The semiconducting properties of the polymer are determined and full color can be achieved. Such polymers are called π-conjugated polymers.

An electroluminescent device using poly (p-phenylenevinylene) (PPV), a polymer having conjugated double bonds, was first introduced in 1990 by a team of professors from RH Friend at the University of Cambridge, UK. After it was announced, research using organic polymers has been actively conducted. The polymer is superior in heat resistance to low molecular weight, and ink-jet printing and spin coating are possible, which facilitates enlargement of the display device. As light emitting materials, polyphenylenevinylene (PPV) derivatives, polythiophene (Pth) derivatives, and the like, which can improve workability and express various colors by introducing appropriate substituents, have been reported. However, as materials such as polyphenylenevinylene derivatives and polythiophene derivatives, high efficiency red and green light emitting polymer materials can be obtained among the three primary colors of light, but high efficiency blue light emitting polymer materials can be obtained. it's difficult.

In addition, polyphenylene derivatives, polyfluorene derivatives, and the like have been reported as blue light emitting polymer materials. Polyphenylene has high oxidation stability and thermal stability, but has a disadvantage of low luminous efficiency and poor solubility.

On the other hand, with respect to the polyfluorene derivative, the prior art is as follows:

US Pat. No. 6,255,449 discloses 9-substituted-2,7-dihalofluorene compounds, and oligomers and polymers thereof, suitable as light emitting materials, such as light emitting layers or carrier transport layers of light emitting diodes.

US Patent Nos. 6,309,763 and 6,605,373 introduce electroluminescent copolymers containing florin groups and amine groups in repeat units. According to the 763 patent, such a copolymer is useful as a light emitting layer or a major transport layer of an electroluminescent device.

WO 02/77060 discloses conjugated polymers containing spirofluorene units. According to the patent, the polymer exhibits improved profile properties as a light emitting material for electronic components such as PLEDs.

As described above, studies using polyfluorene derivatives as active blue-molecules have been actively conducted. However, the interaction between excitons produced in one molecule and excitons of other molecules adjacent to each other is improved, efficiency is improved, and lifetime is improved. Has a problem.

Therefore, in the present invention, as a result of extensive research to solve the above problems, it has excellent thermal stability and high luminous efficiency, excellent solubility and can minimize the interaction between molecules, the existing polyfluorene-based (PFs Electroluminescent molecules and electroluminescent devices using the same blue, green, and red host materials including substituted fluorenyl groups having a di-substituted fluorene unit in the 9-position, which significantly improve the disadvantages of It was developed.

Accordingly, an object of the present invention is to exhibit high luminous efficiency by minimizing intermolecular interactions, facilitating energy transfer, suppressing vibronic mode as much as possible, having high thermal and oxidative stability, and high efficiency blue, green and red colors. The present invention provides an electro-molecule advertisement molecule that acts as a host material necessary to implement the present invention.

Another object of the present invention is to provide an electroluminescent device manufactured using the electroluminescent polymer.

Electro-molecular advertising molecule according to the present invention for achieving the above object is characterized in that represented by the formula (1):

In the above formula, R ₁ and R ₂ are the same as or different from each other, a linear or branched alkyl group having 1 to 20 carbon atoms; An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; Linear or branched alkyl groups having 1 to 20 carbon atoms having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si; An aryl group substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si ; An aryl group having 2 to 24 carbon atoms which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; C 2 substituted with at least one substituent selected from the group consisting of a straight or branched chain alkyl group having 1 to 20 carbon atoms and an alkoxy group having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si An aryl group having a heterocycle of ˜24; A C3 to C40 substituted or unsubstituted trialkylsilyl group; C3-C40 substituted or unsubstituted arylsilyl group; C12-C60 substituted or unsubstituted carbazole group; C6-C60 substituted or unsubstituted phenothiazine group; Or a C 6 to C 60 substituted or unsubstituted arylamine group;

R ₃ , R ₄ and R ₅ are the same as or different from each other, hydrogen; Linear or branched alkyl or alkoxy groups having 1 to 20 carbon atoms; An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; Linear or branched alkyl or alkoxy groups having 1 to 20 carbon atoms having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si; An aryl group substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si ; An aryl group having 2 to 24 carbon atoms which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; C 2 substituted with at least one substituent selected from the group consisting of a straight or branched chain alkyl group having 1 to 20 carbon atoms and an alkoxy group having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si An aryl group having a heterocycle of ˜24; A C3 to C40 substituted or unsubstituted trialkylsilyl group; A C3 to C40 substituted or unsubstituted arylsilyl group; C12-C60 substituted or unsubstituted carbazole group; C6-C60 substituted or unsubstituted phenothiazine group; Or a C 6 -C 60 substituted or unsubstituted arylamine group;

a, b and c are the same as or different from each other, and are integers of 1 to 3;

A is an aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; An aryl group substituted with at least one substituent selected from the group consisting of a straight or branched chain alkyl group having 1 to 20 carbon atoms and an alkoxy group having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si ; An aryl group having 2 to 24 carbon atoms which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; Or carbon atoms substituted with at least one substituent selected from the group consisting of a straight or branched chain alkyl group having 1 to 20 carbon atoms and an alkoxy group having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si Aryl group having 2 to 24 heterocycles;

Ar is selected from the group consisting of C6-C60 substituted or unsubstituted aromatic compounds, C2-C60 substituted or unsubstituted heteroaromatic compounds, and combinations thereof; And,

l is an integer from 1 to 100,000, m is an integer from 0 to 100,000, n is an integer from 1 to 100,000.

Electroluminescent device according to the present invention for achieving the above another object has at least one layer containing the organic electroluminescent molecules between the anode and the cathode, wherein the layer is an interface layer, a hole transport layer, a light emitting layer, an electron transport layer Or a hole blocking layer.

Hereinafter, the present invention will be described in more detail with reference to the accompanying drawings.

As described above, in the present invention, 9-fluoren-2-yl-9-aryl-2,7 which can be used as a host material of high purity blue, green and red having high solubility, high thermal stability and high quantum efficiency Provided are electroluminescent molecules containing fluorenyl units and electroluminescent devices using the same.

The electro-adhesive molecule according to the present invention is a material having properties of excellent thermal stability, light stability, solubility, film formability and high quantum efficiency, thereby introducing a fluorenyl group which is a large substituent at the 9-position of fluorene used as the main chain. The substituent has the same structure as the main chain, and the arrangement between the main chain and the substituent is random, and the characteristic that the intermolecular excimer by the substituent is suppressed to the maximum is expressed, so that the most of the polyfluorenes Aggregation and / or excimer formation, which is one of the major problems, are extremely suppressed, and intramolecular or intermolecular energy transfer from the short wavelength substituent to the main chain is possible.

In addition, the 9-position of the fluorene group used as the main chain is suppressed the rotational and vibrational mode by the substituted large fluorenyl group, which serves to greatly reduce the non-radiative decay (organic electro-adhesive molecule of the present invention) Exhibits excellent color purity, brightness and high efficiency of light emission characteristics.

The electro-adhesive molecule containing 9-fluoren-2-yl-9-aryl-2,7-fluorenyl unit according to the present invention is represented by the following Chemical Formula 1:

Formula 1

In the above formula, R ₁ and R ₂ are the same as or different from each other, a linear or branched alkyl group having 1 to 20 carbon atoms; An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; Linear or branched alkyl groups having 1 to 20 carbon atoms having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si; An aryl group substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si ; An aryl group having 2 to 24 carbon atoms which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; C 2 substituted with at least one substituent selected from the group consisting of a straight or branched chain alkyl group having 1 to 20 carbon atoms and an alkoxy group having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si An aryl group having a heterocycle of ˜24; A C3 to C40 substituted or unsubstituted trialkylsilyl group; C3-C40 substituted or unsubstituted arylsilyl group; C12-C60 substituted or unsubstituted carbazole group; C6-C60 substituted or unsubstituted phenothiazine group; Or a C 6 to C 60 substituted or unsubstituted arylamine group;

R ₃ , R ₄ and R ₅ are the same as or different from each other, hydrogen; Linear or branched alkyl or alkoxy groups having 1 to 20 carbon atoms; An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; Linear or branched alkyl or alkoxy groups having 1 to 20 carbon atoms having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si; An aryl group substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si ; An aryl group having 2 to 24 carbon atoms which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; Carbon number substituted with at least one substituent selected from the group consisting of a straight or branched chain alkyl group having 1 to 20 carbon atoms and an alkoxy group having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si Aryl groups having 2 to 24 heterocycles; A C3 to C40 substituted or unsubstituted trialkylsilyl group; C3-C40 substituted or unsubstituted arylsilyl group; C12-C60 substituted or unsubstituted carbazole group; C6-C60 substituted or unsubstituted phenothiazine group; Or a C 6 -C 60 substituted or unsubstituted arylamine group;

a, b and c are the same as or different from each other, and are integers of 1 to 3;

A is an aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; An aryl group substituted with at least one substituent selected from the group consisting of a straight or branched chain alkyl group having 1 to 20 carbon atoms and an alkoxy group having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si ; An aryl group having 2 to 24 carbon atoms which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; Or carbon atoms substituted with at least one substituent selected from the group consisting of a straight or branched chain alkyl group having 1 to 20 carbon atoms and an alkoxy group having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si Aryl group having 2 to 24 heterocycles;

Ar is selected from the group consisting of C6-C60 substituted or unsubstituted aromatic compounds, C2-C60 substituted or unsubstituted heteroaromatic compounds, and combinations thereof; And,

l is an integer from 1 to 100,000, m is an integer from 0 to 100,000, n is an integer from 1 to 100,000.

Preferably, R ₁ and R ₂ may each be selected from the following compounds, equal to or different from each other:

Preferably, R ₃ and R ₄ are each the same or different and are selected from the following compounds:

Hydrogen,

Most preferably, R ₃ and R ₄ are each hydrogen.

Preferably, R ₅ may be selected from the following compounds:

Hydrogen,

(I)

,

,

(Ii)

,

,

(Iii)

Where

(Iii) R ₆ and R ₇ are the same as or different from each other, and are linear or branched alkyl groups having 1 to 20 carbon atoms,

Representative examples of such fluorenyl compounds are as follows and may be selected from:

(Ii) R ₈ is hydrogen, a linear or branched alkyl group having 1 to 20 carbon atoms, an alkoxy group or a trialkylsilyl group,

R ₉ and R ₁₀ are the same as or different from each other, and are a straight or branched chain alkyl group having 1 to 20 carbon atoms, and R ₁₁ is hydrogen, a straight or branched chain alkyl group having 1 to 20 carbon atoms, an alkoxy group or a trialkylsilyl group ,

X is O or S, Y and Z are N, and

h and i are the same as or different from each other, and each is an integer of 1 to 3,

Representative examples of aryl compounds having the heterocycles described above are as follows and may be selected from:

And,

(Iii) R ₁₂ , R ₁₃ and R ₁₄ are the same as or different from each other, and a linear or branched alkyl or alkoxy group having 1 to 20 carbon atoms; Or an aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group, and

R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ and R ₂₀ are each the same as or different from each other, hydrogen; Linear or branched alkyl or alkoxy groups having 1 to 20 carbon atoms; Or an aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group,

Representative examples of such silyl compounds, carbazole compounds, phenothiazine compounds and arylamine compounds are as follows and may be selected from:

Most preferably, R ₅ is hydrogen.

Preferably, A may be represented by the following compound:

Wherein R ₂₁ , R ₂₂ and R ₂₃ are the same as or different from each other, hydrogen; Linear or branched alkyl or alkoxy groups having 1 to 20 carbon atoms; Or a straight or branched chain alkyl or alkoxy group having 1 to 20 carbon atoms having at least one hetero atom selected from the group consisting of F, S, N, O, P and Si.

Representative examples of such compounds are as follows and may be selected from:

Preferably, Ar is

(Iii) a C6 to C60 substituted or unsubstituted arylene group;

(Ii) a C2 to C60 substituted or unsubstituted heterocyclic arylene group wherein at least one hetero atom selected from the group consisting of N, S, O, P and Si is included in the aromatic ring;

(Iii) a C 6 to C 60 substituted or unsubstituted arylenevinylene group;

(Iii) a C6-C60 substituted or unsubstituted arylamine group;

(Iii) a C12-C60 substituted or unsubstituted carbazole group; And

(Iii) combinations thereof

Is selected from the group consisting of

Here, Ar is a straight or branched chain alkyl or alkoxy group having 1 to 20 carbon atoms; An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; Cyano group (-CN); Or a silyl group.

More specifically,

(Iii) when Ar is a phenylene group or a fluorenyl group among the substituted or unsubstituted arylene groups of C6 to C60, representative examples of such compounds are as follows, and may be selected from:

(Ii) where Ar is a C2-C60 substituted or unsubstituted heterocyclic arylene group, representative examples of such compounds are as follows and may be selected from:

(Iii) where Ar is a C6 to C60 substituted or unsubstituted arylenevinylene group, representative examples of these compounds are as follows and may be selected from:

(Iii) when Ar is a C6-C60 substituted or unsubstituted arylamine group, representative examples of such compounds are as follows, and may be selected from

Wherein R ₂₄ , R ₂₅ and R ₂₆ are each the same as or different from each other, hydrogen; Linear or branched alkyl or alkoxy groups having 1 to 20 carbon atoms; Or an aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group,

More specifically, it may be selected from the following compounds:

And,

(Iii) when Ar is a substituted or unsubstituted carbazole group of C 12 to C 60, representative examples of such compounds are as follows and may be selected from them;

In the formula, R ₂₇ is a straight or branched chain alkyl or alkoxy group having 1 to 20 carbon atoms; Or an aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group.

In addition, when Ar is a (i) C 6 to C 60 substituted or unsubstituted arylamine group, they may be contained in an amount of about 5 mol% to 15 mol% in the light emitting polymer.

One of the methods for manufacturing the electro-molecule advertising molecule of the present invention as described above is as follows. That is, after preparing monomers through alkylation reaction, bromination reaction, Grignard reaction, etc., organic electroadhesion molecules may be finally prepared through C-C coupling reactions such as Yamamoto coupling reaction and Suzuki coupling reaction. The number average molecular weight of the polymers obtained therefrom is 700 to 10,000,000, and the molecular weight distribution is 1 to 100.

The organic electro-adhesive molecules according to the present invention described above have excellent thermal stability, oxidative stability and solubility, minimize intermolecular interactions, facilitate energy transfer, suppress vibration modes as much as possible, and exhibit blue, green and It can be applied as a red light emitting host.

According to the present invention, the organic electroluminescent molecules are used as a material for forming an interlayer, a light emitting layer, a hole transport layer, an electron transport layer or a hole blocking layer positioned between a pair of electrodes in the electroluminescent device.

The electroluminescent device of the present invention may be configured to further include an interlayer layer, a hole transport layer and an electron transport layer, as well as the most common device configuration of the anode / light emitting layer / cathode.

1 is a cross-sectional view illustrating a structure of a general electroluminescent device composed of a substrate / anode / hole transport layer / light emitting layer / electron transport layer / cathode. Referring to this, a method of manufacturing an electroluminescent device by applying the organic electroluminescent molecule of the present invention is described. The explanation is as follows.

First, a material for the anode 12 electrode is coated on the substrate 11.

Here, the substrate 11 is a substrate used in a conventional electroluminescent device, preferably a glass substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling and waterproof.

In addition, as the material for the anode 12 electrode, indium tin oxide (ITO), tin oxide (SnO ₂ ), zinc oxide (ZnO), or the like, which is transparent and has excellent conductivity, may be used.

Next, the hole transport layer 13 may be formed by vacuum deposition or sputtering on the anode 11 electrode, and the light emitting layer 14 may be formed through a solution coating method such as spin coating or inkjet printing. In addition, the electron transport layer 15 is formed on the light emitting layer 14 before the cathode 16 is formed. At this time, the thickness of the light emitting layer 14 is preferably 5nm ~ 1㎛, preferably 10 ~ 500nm, the thickness of the hole transport layer and the electron transport layer is preferably 10 ~ 10,0001 respectively.

According to the present invention, a material for forming an electron transport layer may be used for the electron transport layer 15, or the compound represented by Chemical Formula 1 may be formed by vacuum deposition, sputtering, spin coating, or inkjet printing.

The hole transport layer 13 and the electron transport layer 15 serves to increase the probability of light emitting coupling in the light emitting polymer by efficiently transporting the carriers to the light emitting polymer. The material for forming the hole transport layer 13 and the electron transport layer 15 usable in the present invention is not particularly limited, but preferably, the material for the hole transport layer 13 is a poly (doped with a poly (styrenesulphonic acid) (PSS) layer. PEDOT: PSS, N, N'-bis (3-methylphenyl) -N, N-diphenyl- [1,1'-biphenyl] -4, which is 3,4-ethylenedioxy-thiophene) (PEDOT), 4'-diamine (TPD) is preferred, and as the electron transport layer material, aluminum trihydroxyquinoline (Alq ₃ ), 1,3,4-oxadiazole derivative PBD (2- (4-biphenylyl) -5 -phenyl-1,3,4-oxadiazole), TPQ (1,3,4-tris [(3-penyl-6-trifluoromethyl) quinoxaline-2-yl] benzene), which is a quinoxaline derivative, and triazole derivatives. .

On the other hand, when the organic electro-adhesive molecule according to the present invention to form a layer through the solution coating method, by blending with polymers having conjugated double bonds, such as other fluorene-based polymers, polyphenylene vinylene-based, polyparaphenylene-based In some cases, binder resins may be mixed and used. Examples of the binder resins include polyvinylcarbazole, polycarbonate, polyester, polyarylate, polystyrene, acrylic polymer, methacrylic polymer, polybutyral, polyvinyl acetal, diallyl phthalate polymer, phenol resin, epoxy resin, Silicone resin, polysulfone resin or urea resin, and these resins may be used individually or in combination.

Optionally, a hole-blocking layer, such as lithium fluoride (LiF), is further formed by vacuum deposition or the like to limit the transfer rate of holes in the light-emitting layer 14 and to bond electron-holes. You can increase the probability.

Finally, a material for the cathode 16 electrode is coated on the electron transport layer 15.

As the cathode forming metal, lithium (Li), magnesium (Mg), calcium (Ca), aluminum (Al), Al: Li, Ba: Li, and Ca: Li having a small work function are used. .

As an example of the electroluminescent device of the present invention which can be manufactured according to the above-described method, the structure of the electroluminescent device according to the preferred embodiment of the present invention is shown in FIGS.

2, an electroluminescent device according to a preferred embodiment of the present invention is a substrate 11, an anode 12, a PEDOT: using a PEDOT: PSS layer (17; 500 kHz), represented by the formula (1) of the present invention The light emitting layer 18 (100-2000 kV) using the electro-molecules to be used, the hole-blocking layer 19 (20 kPa) using the LiF, and the cathode layer 700 kV using the Al may be used.

Referring to FIG. 3, an electroluminescent device according to another preferred embodiment of the present invention includes a substrate 11, an anode 12, a PEDOT: a PPS using a PEDOT: PSS, and Chemical Formula 1 of the present invention. It can be composed of a light emitting layer 21 (100 to 2000 mV) using an electro-molecular molecule represented by < RTI ID = 0.0 > and < / RTI >

The electroluminescent device according to the present invention may be manufactured in the same order as described above, that is, in the order of anode / interior layer / hole transport layer / light emitting layer / electron transport layer / cathode, and vice versa, that is, cathode / electron transport layer / light emitting layer / hole You may manufacture also in order of a transport layer / an interior layer / an anode.

In addition, the organic electroluminescent molecules according to the present invention can be used not only as a polymer organic electroluminescent device but also as a photoconversion material in a photodiode or a semiconductor material in a polymer TFT (Thin Film Transistor).

As described above, the organic electro-adhesive molecule according to the present invention has a fluorenyl group, which is a large substituent in the 9-position of fluorene used as the main chain, so that the substituent has the same structure as the main chain, and thus the arrangement between the main chain and the substituent This randomization results in the characteristic that the intermolecular excimer is suppressed as much as possible by the substituent, thereby suppressing aggregation and / or excimer formation, which is one of the biggest problems of the polyfluorene system. In addition, the intramolecular or intermolecular energy transfer from the short-chain substituent to the main chain is possible, and the 9-position of the fluorene group used as the main chain is non-radiatively attenuated because the rotation and vibration modes are suppressed by the substituted large fluorenyl group. Significantly reduce the thermal stability, light stability, solubility, film formability and properties of high quantum efficiency. Accordingly, the organic electroluminescent molecules of the present invention and organic electroluminescent devices using the same exhibit excellent color purity, brightness and high efficiency characteristics.

Hereinafter, the present invention will be described in more detail with reference to the following examples, but the scope of the present invention is not limited thereto.

※ The following Preparation Examples 1 to 3 were carried out according to the reaction overview shown in FIG.

Production Example 1

-Synthesis of (9- (9 ', 9'-di (2 "-methyl) butylfluoren-2'-yl) -2,7-dibromofluoren-9-ol) (1)

3.3 g (137 mmol) of Mg were added to a 500 mL three neck flask, and 44 g (114 mmol) of 9,9-di (2'-methyl) butyl-2-bromofluorene was dissolved in 200 mL of THF and slowly added to the Grignard reagent. reagent). After the temperature of the reactor was lowered to -40 ° C or lower, 30 g (91 mmol) of 2,7-dibromofluorenone was added under a nitrogen stream, and the temperature was gradually raised to room temperature, followed by stirring for 10 hours. The reaction is poured into water, extracted with diethyl ether and the solvent is blown on a rotary evaporator. 43 g (67 mmol, 73%) of (9- (9 ', 9'-di (2 "-methyl) butylfluorene-2'-yl) -2,7-dibromoflu separated by column chromatography Oren-9-ol) (1).

Production Example 2

- (1,2-di (2-methyl) butyloxy benzene) (2)

In a 500 mL round flask, 20 g (91 mmol) of compound catechol and 107 g (436 mmol) of 2-methyl butyl p-toluenesulfonate were dissolved in 200 mL of DMSO, and then 53 g (473 mmol) of potassium tert-butoxide (t-BuOK) were added slowly. And reacted at 70 ° C. for 12 hours. The reaction was poured into 500 mL of water, extracted using methylene chloride, the solvent was removed by rotary evaporator, and separated by column chromatography using hexane and ethyl acetate mixed solvent (1,2-di (2). 37 g (148 mmol, 81%) of -methyl) butyloxy benzene (2) were obtained.

Production Example 3

2,7-dibromo-9- (9 ', 9'-di (2 "' -metylbutyl) fluoren-2'-yl) -9- (3", 4 "-di (2" "-methyl) butyloxyphenyl) Synthesis of fluorene (3)

50 g (78 mmol) of the compound (1) (9- (9 ', 9'-di (2 "-methyl) buylfluoren-2'-yl) -2,7-dibromofluoren-9-ol) in a 2 L round flask (2) 23.3 g (93 mmol) of (1,2-di (2-methyl) butyloxy benzene) was dissolved in 1000 ml of dichloromethane, the temperature was lowered to 0 ° C., and 7.5 g (78 mmol) of methanesulfonic acid was diluted with 100 ml of dichloromethane. The solution dissolved in was slowly poured and stirred for 2 hours, the reaction was poured into water, extracted with diethyl ether, the solvent was blown on a rotary evaporator, and separated by column chromatography to obtain compound 2,7-dibromo-9. -(9 ', 9'-di (2 "'-methylbutyl) fluorene-2'-yl) -9- (3", 4 "-di (2" "-methyl) butyloxyphenyl) fluorene ( 67 g (65 mmol, 84%) was obtained.

Meanwhile, ¹ H-NMR spectrum of Compound (3) prepared therefrom is shown in FIG. 5.

Example 1

Poly (9- (9 ', 9'-di (2 "'-metylbutyl) fluoren-2'-yl) -9- (3", 4 "-di (2" "-methyl) butyloxyphenyl) -2, 7-fluorenyl) (Formula 2)

Wherein n ₁ is an integer from 1 to 100,000.

6 g (9.25 mmol) of Compound (3) was added to a 500 mL Schlenk flask, which was dissolved in 60 mL of toluene degassed with nitrogen and stored under nitrogen. 5.780 g (21.01 mmol) of Ni (COD) ₂ , 1.45 g (13.42 mmol) of 1.4-cyclooctadiene (COD) and 3.224 g (21.28 mmol) of dipyridyl were added to a Schlenk flask under nitrogen and 240 mL of degassed toluene and 60 mL of DMF were added and then stirred at 80 ° C. for 30 minutes. The monomer solution prepared above was added to the reaction vessel, reacted for 150 hours, 2 mL of bromobenzene was added, and then terminated by reacting for 24 hours. After the reaction was completed, a reaction solution was added to 1500 mL of a hydrochloric acid (35w%): acetone: ethanol = 1: 1: 1 solution to remove the unreacted catalyst and to precipitate a polymer. After filtering the polymer was dissolved in chloroform and filtered again with celite to remove the residual catalyst, concentrated and reprecipitated in methanol and washed with Soxhlet for 24 hours. Yield 63%, Mw = 166,000, Mn = 80,000, PDI (polydispersity) = 2.08

On the other hand, ¹ H-NMR spectrum of the electro-adhesive molecules prepared therefrom is shown in FIG.

Example 2

-Synthesis of Polymer of Formula 3

A polymer of Chemical Formula 3 was synthesized according to Scheme 1 below.

In the above formula, l ₁ is an integer of ₁ to 100,000, and m ₁ is an integer of ₁ to 100,000.

A polymer was synthesized in the same manner as in Example 1, except that 87 mol% of the compound (3) and 13 mol% of the compound B were used as the monomer. Mw = 230,000, Mn = 87,000, PDI = 2.64

Example 3

-Synthesis of Polymer of Formula 4

A polymer of Chemical Formula 4 was synthesized according to Scheme 2 below.

In the above formula, l ₂ is an integer of ₁ to 100,000, and m ₂ is an integer of ₁ to 100,000.

A polymer was synthesized in the same manner as in Example 1, except that 90 mol% of the compound (3) and 10 mol% of the compound C were used as the monomer. Mw = 218,000, Mn = 77,000, PDI = 2.83

Examples 4-6

-Manufacturing of electroluminescent device

After forming an indium-tin oxide (ITO) electrode on the glass substrate, as shown in Table 1 on the top of the ITO electrode by spin coating the polymer for an electroluminescent device to form a light emitting layer of 400 ~ 1500Å thickness. Al: Li was vacuum-deposited on the light emitting layer to form an aluminum-lithium electrode having a thickness of 100 to 1200 Å, to fabricate an organic electroluminescent device, and the light emission characteristics thereof were shown in Table 1 below.

Light emitting layer Drive start voltage EL λmax
(Nm) Highest efficiency
(cd / A) Color coordinates
(x, y) Example 4 (2) 4.5V 422 0.14 0.147, 0.050 Example 5 (3) 3.5V 448 1.45 0.149, 0.119 Example 6 Formula 4 4.0V 460 2.51 0.152, 0.133

7 is an electroluminescence spectrum obtained from an electroluminescent device (Example 4) prepared using an electroluminescent molecule represented by Chemical Formula 2 of the present invention as a light emitting layer material, and its maximum peak was 422 nm, which is a blue light emitting region, and polyfluorene. The peak by the excimer near 530 nm which appeared in the electroluminescence spectrum of the system did not appear, and the highest efficiency was 0.14 cd / m <^2> and showed a high value. It is extremely inhibited intermolecular or intramolecular excimer and aggregation by the fluorenyl group substituted at the 9-position of fluorene, greatly suppressed rotation and vibration movement by the large fluorenyl group, band gap The result is an energy transfer from the fluorenyl group substituted in the large side chain to the main chain having a smaller band gap. In addition, as shown in Example 4 of Table 1, the color coordinates were x, y = 0.147, 0.050, it was found that the light emission in the ultraviolet region than NTSC standard blue (NT, standard blue; x, y = 0.16, 0.08).

From this result, Compound 2 is judged to be an excellent host material when preparing electroluminescent polymers in all areas such as blue, green, yellow, and red luminescence having excellent color purity.

FIG. 8 is an electroluminescence spectrum obtained from an electroluminescent device (Example 6) of an electroluminescent molecule represented by Chemical Formula 4 of the present invention, and the maximum peak is about 460 nm in the blue emission region. The color coordinates of) are superior to the known blue light-emitting polymer materials using diamine derivatives substituted with alkoxyphenyl, and peaks by excimers near 530 nm which appear in the polyfluorene-based electroluminescence spectrum are not observed. The efficiency was high as 1.45 cd / m ² .

In addition, Figure 9 is a curve showing the luminance according to the voltage obtained from the electroluminescent device (Example 5) of the electroluminescent molecules represented by the formula (3) of the present invention, even though the polymer of the formula (3) has a bulky substituent The voltage showed a low value of 3.5 V, and it was determined that the luminance increased stably with increasing driving voltage, and thus the film formation by spin coating was excellent.

As described above, Examples 5 and 6 show the characteristics of the electroluminescent devices prepared from the electroluminescent polymer polymerized using the amine monomer to improve the compound (3) and the hole transport and injection properties, driving The voltage was decreased and the luminous efficiency was greatly increased. Even though TPD-based amine was used, the light was emitted in the blue light emitting region with excellent color purity.

As described above, the electro-adhesive molecules according to the present invention have excellent thermal stability and high luminous efficiency, have excellent solubility and minimize intermolecular interactions, and significantly improve the shortcomings of the conventional polyfluorene system. It can be used as a host material such as blue, green and red of the light emitting device can exhibit excellent light emission characteristics.

It is apparent that modifications and improvements are possible by those skilled in the art within the spirit or scope of the present invention. Accordingly, it is intended that the present invention cover the modifications and variations of this invention provided they come within the scope of the appended claims and their equivalents.

Claims (14)

An electroadhesive molecule containing a 9-fluoren-2-yl-9-aryl-2,7-fluorenyl unit represented by Formula 1, wherein a substituted fluorenyl group is introduced at the 9-position of fluorene: Formula 1

  In the formula, R 'and R2 are the same as or different from each other, a linear or branched alkyl group having 1 to 20 carbon atoms; An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; An aryl group having 2 to 24 carbon atoms which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; A C3 to C40 substituted or unsubstituted trialkylsilyl group; C3-C40 substituted or unsubstituted arylsilyl group; C12-C60 substituted or unsubstituted carbazole group; C6-C60 substituted or unsubstituted phenothiazine group; Or a C 6 to C 60 substituted or unsubstituted arylamine group; R ₃ , R₄ and R ₅ are the same as or different from each other, hydrogen; Linear or branched alkyl or alkoxy groups having 1 to 20 carbon atoms; An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; An aryl group having 2 to 24 carbon atoms which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; A C3 to C40 substituted or unsubstituted trialkylsilyl group; C3-C40 substituted or unsubstituted arylsilyl group; C12-C60 substituted or unsubstituted carbazole group; C6-C60 substituted or unsubstituted phenothiazine group; Or a C 6 -C 60 substituted or unsubstituted arylamine group; a, b and c are the same as or different from each other, and are integers of 1 to 3; A has the following structure,

Wherein R ₂₁ , R ₂₂ and R ₂₃ are the same as or different from each other, hydrogen; A linear or branched alkyl or alkoxy group having 1 to 20 carbon atoms; Ar is a C6 to C60 substituted or unsubstituted aromatic compound, C2 to C60 substituted or unsubstituted heteroaromatic compound, C6 to C60 substituted or unsubstituted arylenevinylene group, C6 to C60 substituted or unsubstituted An arylamine group (wherein the C6 to C60 substituted or unsubstituted arylenevinylene group, C6 to C60 substituted or unsubstituted arylamine group is a linear or branched alkyl or alkoxy group having 1 to 20 carbon atoms or 1 to 20 carbon atoms An aryl group cyano group (-CN) unsubstituted or substituted with at least one substituent selected from the group consisting of an alkyl group and an alkoxy group of a linear or branched chain thereof, and a silyl group) and a combination thereof , l is an integer from 1 to 100,000, m is an integer from 0 to 100,000, and n is an integer from 1 to 100,000. An electroadhesive molecule containing a 9-fluoren-2-yl-9-aryl-2,7-fluorenyl unit represented by Formula 1, wherein a substituted fluorenyl group is introduced at the 9-position of fluorene: Formula 1

R _₁ and R 2 are each the same as or different from each other, and are selected from the following compounds,

R ₃ , R₄ and R ₅ are the same as or different from each other, hydrogen; Linear or branched alkyl or alkoxy groups having 1 to 20 carbon atoms; An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; An aryl group having 2 to 24 carbon atoms which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; A C3 to C40 substituted or unsubstituted trialkylsilyl group; C3-C40 substituted or unsubstituted arylsilyl group; C12-C60 substituted or unsubstituted carbazole group; C6-C60 substituted or unsubstituted phenothiazine group; Or a C 6 -C 60 substituted or unsubstituted arylamine group; a, b and c are the same as or different from each other, and are integers of 1 to 3; A has the following structure,

Wherein R ₂₁ , R ₂₂ and R ₂₃ are the same as or different from each other, hydrogen; A linear or branched alkyl or alkoxy group having 1 to 20 carbon atoms, Ar is a C6 to C60 substituted or unsubstituted aromatic compound, C2 to C60 substituted or unsubstituted heteroaromatic compound, C6 to C60 substituted or unsubstituted arylenevinylene group, C6 to C60 substituted or unsubstituted An arylamine group (wherein the C6 to C60 substituted or unsubstituted arylenevinylene group, C6 to C60 substituted or unsubstituted arylamine group is a linear or branched alkyl or alkoxy group having 1 to 20 carbon atoms or 1 to 20 carbon atoms An aryl group cyano group (-CN) unsubstituted or substituted with at least one substituent selected from the group consisting of an alkyl group and an alkoxy group of a linear or branched chain thereof, and a silyl group) and a combination thereof , l is an integer from 1 to 100,000, m is an integer from 0 to 100,000, and n is an integer from 1 to 100,000. An electroadhesive molecule containing a 9-fluoren-2-yl-9-aryl-2,7-fluorenyl unit represented by Formula 1, wherein a substituted fluorenyl group is introduced at the 9-position of fluorene: Formula 1

In the formula, R 'and R2 are the same as or different from each other, a linear or branched alkyl group having 1 to 20 carbon atoms; An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; An aryl group having 2 to 24 carbon atoms which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; A C3 to C40 substituted or unsubstituted trialkylsilyl group; C3-C40 substituted or unsubstituted arylsilyl group; C12-C60 substituted or unsubstituted carbazole group; C6-C60 substituted or unsubstituted phenothiazine group; Or a C 6 to C 60 substituted or unsubstituted arylamine group; R ₃ and R ₄ are each the same as or different from each other, and are selected from the following compounds, Hydrogen,

R ₅ is hydrogen; Linear or branched alkyl or alkoxy groups having 1 to 20 carbon atoms; An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; An aryl group having 2 to 24 carbon atoms which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; A C3 to C40 substituted or unsubstituted trialkylsilyl group; C3-C40 substituted or unsubstituted arylsilyl group; C12-C60 substituted or unsubstituted carbazole group; C6-C60 substituted or unsubstituted phenothiazine group; Or a C 6 -C 60 substituted or unsubstituted arylamine group; a, b and c are the same as or different from each other, and are integers of 1 to 3; A has the following structure,

Wherein R ₂₁ , R ₂₂ and R ₂₃ are the same as or different from each other, hydrogen; C1-C20 linear or branched alkyl or alkoxy groups Ar is a C6 to C60 substituted or unsubstituted aromatic compound, C2 to C60 substituted or unsubstituted heteroaromatic compound, C6 to C60 substituted or unsubstituted arylenevinylene group, C6 to C60 substituted or unsubstituted An arylamine group (wherein the C6 to C60 substituted or unsubstituted arylenevinylene group, C6 to C60 substituted or unsubstituted arylamine group is a linear or branched alkyl or alkoxy group having 1 to 20 carbon atoms or 1 to 20 carbon atoms An aryl group cyano group (-CN) unsubstituted or substituted with at least one substituent selected from the group consisting of an alkyl group and an alkoxy group of a linear or branched chain thereof, and a silyl group) and a combination thereof , l is an integer from 1 to 100,000, m is an integer from 0 to 100,000, and n is an integer from 1 to 100,000. An electroadhesive molecule containing a 9-fluoren-2-yl-9-aryl-2,7-fluorenyl unit represented by Formula 1, wherein a substituted fluorenyl group is introduced at the 9-position of fluorene: Formula 1

In the formula, R 'and R2 are the same as or different from each other, a linear or branched alkyl group having 1 to 20 carbon atoms; An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; An aryl group having 2 to 24 carbon atoms which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; A C3 to C40 substituted or unsubstituted trialkylsilyl group; C3-C40 substituted or unsubstituted arylsilyl group; C12-C60 substituted or unsubstituted carbazole group; C6-C60 substituted or unsubstituted phenothiazine group; Or a C 6 to C 60 substituted or unsubstituted arylamine group; R 3 and R VII are the same as or different from each other, hydrogen; Linear or branched alkyl or alkoxy groups having 1 to 20 carbon atoms; An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; An aryl group having 2 to 24 carbon atoms which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; A C3 to C40 substituted or unsubstituted trialkylsilyl group; C3-C40 substituted or unsubstituted arylsilyl group; C12-C60 substituted or unsubstituted carbazole group; C6-C60 substituted or unsubstituted phenothiazine group; Or a C 6 -C 60 substituted or unsubstituted arylamine group; R ₅ is selected from the following compounds, Hydrogen,

Where R ₆ and R ₇ are the same as or different from each other, and are linear or branched alkyl groups having 1 to 20 carbon atoms, R ₈ is hydrogen, a linear or branched alkyl group having 1 to 20 carbon atoms, an alkoxy group or a trialkylsilyl group, R ₉ and R ₁₀ are the same as or different from each other, and are a straight or branched chain alkyl group having 1 to 20 carbon atoms, and R ₁₁ is hydrogen, a straight or branched chain alkyl group having 1 to 20 carbon atoms, an alkoxy group or a trialkylsilyl group , X is O or S, Y and Z are N, h and i are the same as or different from each other, each is an integer of 1 to 3, R ₁₂ , R ₁₃ and R ₁₄ are the same as or different from each other, at least one selected from the group consisting of a straight or branched chain alkyl or alkoxy group having 1 to 20 carbon atoms or a straight or branched chain alkyl group and alkoxy group having 1 to 20 carbon atoms An aryl group which is unsubstituted or substituted with a substituent of, and R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ and R ₂₀ are each the same as or different from each other, hydrogen; An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a straight or branched chain alkyl group or alkoxy group having 1 to 20 carbon atoms or a straight or branched chain alkyl group and alkoxy group having 1 to 20 carbon atoms. a, b and c are the same as or different from each other, and are integers of 1 to 3; A has the following structure,

Wherein R ₂₁ , R ₂₂ and R ₂₃ are the same as or different from each other, hydrogen; A linear or branched alkyl or alkoxy group having 1 to 20 carbon atoms, Ar is a C6 to C60 substituted or unsubstituted aromatic compound, C2 to C60 substituted or unsubstituted heteroaromatic compound, C6 to C60 substituted or unsubstituted arylenevinylene group, C6 to C60 substituted or unsubstituted An arylamine group (wherein the C6 to C60 substituted or unsubstituted arylenevinylene group, C6 to C60 substituted or unsubstituted arylamine group is a linear or branched alkyl or alkoxy group having 1 to 20 carbon atoms or 1 to 20 carbon atoms An aryl group cyano group (-CN) unsubstituted or substituted with at least one substituent selected from the group consisting of an alkyl group and an alkoxy group of a linear or branched chain thereof, and a silyl group) and a combination thereof , l is an integer from 1 to 100,000, m is an integer from 0 to 100,000, and n is an integer from 1 to 100,000. According to claim 1, wherein R ₃ , R ₄ and R ₅ are each electro-molecules, characterized in that the hydrogen. delete The method of claim 1, wherein Ar is: (Iii) a C6 to C60 substituted or unsubstituted arylene group; (Ii) a C2 to C60 substituted or unsubstituted heterocyclic arylene group wherein at least one hetero atom selected from the group consisting of N, S, O, P and Si is included in the aromatic ring; (Iii) a C12-C60 substituted or unsubstituted carbazole group; And (Iii) combinations thereof Is selected from the group consisting of Here, the substituent of Ar may be a linear or branched alkyl or alkoxy group having 1 to 20 carbon atoms; An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms and an alkoxy group; Cyano group (-CN); And a silyl group, wherein the electric foot advertisement molecule is selected from the group consisting of. According to claim 1, wherein when Ar is a C6-C60 substituted or unsubstituted arylamine group, the content of Ar in the electro-adsorption molecule is characterized in that the electro-adsorption molecule is 5 to 15 mol%. [Claim 2] The electro-adhesive molecule according to claim 1, wherein the electro-adhesive molecule has a number average molecular weight of 700 to 10,000,000 and a molecular weight distribution of 1 to 100. According to claim 1, wherein the electro-molecular advertising molecule is an electro-molecular advertising molecule, characterized in that the compound represented by the formula (2): (2)

Wherein n ₁ is an integer from 1 to 100,000. According to claim 1, wherein the electro-molecular advertising molecule is an electro-molecular advertising molecule, characterized in that the compound represented by the following formula (3): (3)

Wherein l ₁ is an integer from ₁ to 100,000, and m ₁ is an integer from ₁ to 100,000. According to claim 1, wherein the electro-molecular advertising molecule is an electro-molecular advertising molecule, characterized in that the compound represented by the following formula (4): Formula 4

Wherein l ₂ is an integer from ₁ to 100,000, and m ₂ is an integer from ₁ to 100,000. An electroluminescent device having at least one layer comprising an electroluminescent molecule according to claim 1 between an anode and a cathode, wherein said layer is an interlayer, a hole transport layer, a light emitting layer, an electron transport layer or a hole blocking layer. The structure of claim 13, wherein the structure of the electroluminescent device is an anode / light emitting layer / cathode, an anode / interlayer layer / light emitting layer / cathode, an anode / interlayer layer / hole transport layer / light emitting layer / cathode, or an anode / interlayer layer / hole transport layer Electroluminescent device, characterized in that / light emitting layer / electron transport layer / cathode.

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