KR20070016594A - Distyrylbenzene Derivatives, Organic Electroluminescent Polymer Prepared Therefrom, and Electroluminescent Device Manufactured Using the Same - Google Patents

Abstract

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to an organic baler molecule, and more particularly, to a specific distyrylbenzene-based derivative effective for improving luminescence performance and to an organic baler molecule polymerized using the monomer. The electro-molecules prepared from the monomers according to the present invention are fused by bulky substituents to the distyrylbenzene moiety in the main chain, and have high solubility, high photostability and thermal stability, film formability and high purity with high quantum efficiency. It can be used as a host material such as blue, green and red.

Light emitting polymer, light emitting device, blue light emitting, quantum efficiency, distyryl benzene,

Description

Distyrylbenzene Derivatives, Organic Electroluminescent Polymer Prepared Therefrom, and Electroluminescent Device Manufactured Using the Same}

1 is a cross-sectional view of a general organic electroluminescent device having a structure of a substrate / anode / hole transport layer / light emitting layer / electron transport layer / cathode;

2 is a view schematically showing a synthesis mechanism of Compound S6 prepared according to Preparation Example 1 of the present invention;

FIG. 3 is a schematic view showing a synthesis mechanism of Compound S9 prepared according to Preparation Example 2 of the present invention; FIG.

FIG. 4 is a schematic view showing a synthesis mechanism of compounds S7 and S11 prepared according to Preparation Examples 3 and 4 of the present invention, respectively; FIG. And

5 is an electroluminescence spectrum obtained from an electroluminescent device using organic light emitting molecules prepared according to Example 2 and Comparative Example 2 of the present invention.

* Description of the symbols for the main parts of the drawings *

11 substrate 12 anode

13: hole transport layer

14 light emitting layer

15: electron transport layer

16: cathode

The present invention relates to a monomer for preparing a light emitting polymer effective for improving light emission performance and a light emitting polymer prepared therefrom. More specifically, the present invention is an organic electric having excellent color purity, high solubility, high light and thermal stability, film formability and high quantum efficiency by fusion of bulky substituents to distyrylbenzene moiety in the main chain. The present invention relates to a monomer for preparing a light emitting polymer. In addition, the present invention relates to an organic electroluminescent molecule prepared by polymerization or copolymerization from the monomer and 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.

Until now, most displays are light-receiving, while self-emissive electroluminescence displays are fast response and self-emissive, so they don't need backlighting and have excellent brightness. It is attracting attention as a display element.

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 of these organic materials was reported by Pope et al. In 1963, and in 1987 by Tang et al. At Eastmann Kodak, alumina-quinone. Many studies have been conducted since a light emitting device having a multilayer structure having a quantum efficiency of 1% and a luminance of 1000 cd / m 2 at 10 V or less as a device manufactured from a pigment having a π-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 organic 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 organic 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 moved 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 organic electroluminescent device driven on the principle described above 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 being announced, researches using organic polymers have been actively conducted. The polymer has excellent heat resistance compared to the low molecule, and inkjet printing and spin coating are possible, which makes it easy to increase the size of the display device. By introducing various suitable substituents, polyphenylenevinylene (PPV) derivatives, polythiophene (Pth) derivatives, and the like, which can improve processability and express various colors, 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. Although researches using polyfluorene derivatives as active blue molecules have been actively conducted, there are still problems such as minimizing the interaction between excitons produced in one molecule and the excitons of other molecules, improving efficiency and improving lifetime. .

On the other hand, light emitting polymers containing a distyrylbenzene moiety in the backbone of the organic electroluminescent advertisement molecule are known. For example, US Pat. No. 5,514,878 discloses conjugated polymers consisting of conjugated and non-conjugated regions consisting of distyrylbenzen moieties. U. S. Patent No. 5,653, 914 also discloses an electroluminescent device having a light emitting layer consisting of a processable polymer matrix and a chromogenic component, distyrylbenzene. However, the organic light-emitting polymer disclosed in the above-described prior art still has room for improvement in terms of required properties such as color purity, in particular, high purity blue light emission property, even though it contains a distyrylbenzene moiety.

In order to solve the above-mentioned problems of the prior art, the present inventors have continuously studied, it is possible to minimize the intermolecular interaction excellent in solubility, light emission of a conventional light emitting polymer, especially a light emitting polymer having a distyrylbenzene moiety It is to develop a new distyryl benzene derivative and a polymer or copolymer using the same as the monomer of the electroadhesive molecule which can significantly improve the efficiency and color purity and can be used as a host material such as blue, green and red.

Accordingly, an object of the present invention is to have high thermal and oxidative stability, to minimize intermolecular interactions, to facilitate energy transfer, to suppress vibronic mode as much as possible, and to exhibit excellent luminous efficiency, and high efficiency and high purity blue color, It is to provide a novel distyrylbenzene-based derivative useful as a monomer for preparing an organic electroadhesive molecule which acts as a host material necessary to realize green and red (especially blue).

Another object of the present invention is to provide an organic electroadhesion molecule polymerized or copolymerized using a novel distyrylbenzene-based derivative.

Still another object of the present invention is to provide an electroluminescent device manufactured using the organic electroluminescent advertising molecule.

In order to achieve the above object, a distyryl benzene derivative useful as a monomer for preparing an organic electroluminescent advertisement molecule provided according to one embodiment of the present invention is represented by the following formula (1) or (2):

( Structure 1 )

( Structure Formula 2 )

In the above, R ₁ to R ₁₈ are each independently 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; C 1-20 straight or branched chain alkyl or alkoxy group 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 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; 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; Substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms; Substituted or unsubstituted arylsilyl group having 3 to 40 carbon atoms; Substituted or unsubstituted carbazole groups having 12 to 60 carbon atoms; Substituted or unsubstituted phenothiazine group having 6 to 60 carbon atoms; Or a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; And

또는

임.X ₁ , X ₂ , X ₃ and X ₄ are each independently Cl, Br, I, B (OH) ₂ ,

or

being.

The organic bald advertisement molecule provided according to another embodiment of the present invention is represented by the following structural formula 3:

( Structure Formula 3 )

In the above, R ₁ to R ₁₈ are the same as above;

Ar is selected from the group consisting of a substituted or unsubstituted aromatic compound having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaromatic compound having 2 to 60 carbon atoms, and a combination thereof;

l and m are each an integer of 0 to 1,000, except that both l and m become 0;

n is an integer from 1 to 20,000; And

p is an integer of 0-10,000.

According to another embodiment of the present invention, there is provided at least one layer comprising the organic electroluminescent molecules represented by the structural formula 3 between the anode and the cathode, the layer is a hole transport layer, a light emitting layer, an electron transport layer or a hole blocking (hole) Provided is an organic electroluminescent device, which is a blocking layer.

The invention can be achieved according to the following description with reference to the accompanying drawings.

As described above, the present invention provides excellent color purity, high solubility, high light stability and thermal stability, film forming, which can be used as host materials such as high purity blue, green and red having high solubility, high thermal stability and high quantum efficiency. The present invention relates to a distyrylbenzene derivative useful as a monomer in the preparation of an organic electroadhesive molecule having high properties and high quantum efficiency. In addition, an organic electroluminescent advertisement molecule prepared by polymerization or copolymerization using the distyrylbenzene derivative and an electroluminescent device using the same are provided.

The distyrylbenzene derivative provided according to the present invention is a form in which a bulky substituent is fused to a distyrylbenzene moiety, and in the case of a light emitting polymer prepared using the monomer, the substituents fused with the main chain are arranged in a vertical form to intermolecularly. Excimer formation and / or aggregation is characterized as suppressed as much as possible. In particular, compared with the light emitting polymer having a distyrylbenzene moiety in the main chain in the related art, it is possible to give excellent properties of color purity and physical properties. It also enables intramolecular or intermolecular energy transfer to long-wavelength distyrylbenzene moieties in the main chain, and bulk transfers fused to distyrylbenzene moieties result in energy transfer from the substituents to the main chain or from the main chain to the substituents. It is possible to give an improvement in the luminous efficiency. In addition, the rotation and vibration modes are suppressed by the large substituents fused to the distyrylbenzene moiety, which can greatly reduce non-radiative decay, resulting in high-efficiency light emission characteristics and excellent color purity, brightness and Has efficiency.

Distyrylbenzene derivatives according to the invention are represented by the following formula (1) or (2):

Structural Formula 1

Structural Formula 2

In the above, R ₁ to R ₁₈ are each independently 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 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; 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; Substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms; Substituted or unsubstituted arylsilyl group having 3 to 40 carbon atoms; Substituted or unsubstituted carbazole groups having 12 to 60 carbon atoms; Substituted or unsubstituted phenothiazine group having 6 to 60 carbon atoms; Or a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; And

또는

이다.X ₁ , X ₂ , X ₃ and X ₄ are each independently Cl, Br, I, B (OH) ₂ ,

or

to be.

The distyrylbenzene derivatives described above can be synthesized using individual reactions known in the art, typically involving alkylation reactions, bromination reactions, Grignard reactions, Wittig reactions, and the like. In this regard, more specific synthesis mechanisms are shown in FIGS. 2 and 3 and are described in detail in the examples below. It should be noted, however, that the present invention is not necessarily limited to this specific synthetic mechanism.

According to a preferred embodiment of the present invention, representative examples of R ₁ to R ₁₈ are as follows.

Hydrogen,

(Ⅰ)

(Ii)

(Ⅲ)

Where

(Iii) R ₁₉ and R ₂₀ are each independently a linear or branched alkyl group having 1 to 20 carbon atoms;

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

(Ii) R ₂₁ is hydrogen, a linear or branched alkyl, alkoxy or trialkylsilyl group having 1 to 20 carbon atoms,

R ₂₂ and R ₂₃ are each independently a linear or branched alkyl group having 1 to 20 carbon atoms,

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

a is an integer of 1-3.

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

And,

(Iii) R ₂₄ , R ₂₅ and R ₂₆ are each independently 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 ₂₇ , R ₂₈ , R ₂₉ , R ₃₀ , R ₃₁ and R ₃₂ are each independently 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:

In addition, according to a preferred aspect of the present invention, representative examples of R ₇ and R ₁₆ are as follows:

Hydrogen,

On the other hand, the compounds of the formula 1 and formula 2 synthesized as described above are represented by the following formula 3, synthesized through polymerization or copolymerization.

Structural Formula 3

In the above, R ₁ to R ₁₈ are the same as above;

Ar is selected from the group consisting of a substituted or unsubstituted aromatic compound having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaromatic compound having 2 to 60 carbon atoms, and a combination thereof;

l and m are each an integer of 0 to 1,000, except that both l and m become 0;

n is an integer from 1 to 20,000; And

p is an integer of 0-10,000.

That is, in the case of the polymer represented by the above formula, residues derived from the formula 1 or 2 in the main chain alone (that is, when l is 0 or m is 0 in the formula 3) or in the bound form (that is, in the formula 3) And m are both nonzero). As the polymerization or copolymerization method, any method known in the art may be adopted. Preferably, the polymerization or copolymerization may be carried out through a C-C coupling reaction such as a Yamamoto coupling reaction or a Suzuki coupling reaction.

In addition, in the present invention, the main chain may optionally include other functional groups as well as specific distyrylbenzenes derived from the above-described formulas (1) and (2), and is a component represented by Ar in formula (3). That is, Ar is introduced as a component copolymerized with the monomers of Formula 1 and / or Formula 2 to modify the optical properties, electrical properties, and the like of the light emitting polymer. In this case, the structural formula 3 is preferably introduced so that the ratio of n: p is about 100: 1 to 100: 30, and more preferably about 100: 5 to 100: 20. Representative examples of the Ar component are as follows:

(Iii) a substituted or unsubstituted arylene group having 6 to 60 carbon atoms;

(Ii) a substituted or unsubstituted heterocyclic arylene group having 2 to 60 carbon atoms in which 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 substituted or unsubstituted arylenevinylene group having 6 to 60 carbon atoms;

(Iii) a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms;

(Iii) a substituted or unsubstituted carbazole group having 12 to 60 carbon atoms; And

(Iii) combinations thereof

Is selected from the group consisting of

And, 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 substituent such as a silyl group.

More specifically,

(Iii) When Ar is a phenylene group or a fluorenyl group among the substituted or unsubstituted arylene groups having 6 to 60 carbon atoms, representative examples of these compounds are as follows, and may be selected from:

(Ii) when Ar is a substituted or unsubstituted heterocyclic arylene group having 2 to 60 carbon atoms, representative examples of such compounds are as follows and may be selected from:

(Iii) when Ar is a substituted or unsubstituted arylenevinylene group having 6 to 60 carbon atoms, representative examples of such compounds are as follows, and may be selected from:

(Iii) when Ar is a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms, representative examples of such compounds are as follows, and may be selected from

In the above formula, R ₃₃ , R ₃₄ and R ₃₅ are each independently 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 having 12 to 60 carbon atoms, representative examples of such compounds are as follows and may be selected from them;

In the formula, R ₃₆ is a straight or branched chain alkyl group 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 particular, when Ar is (i) a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms, they may be contained in an amount of about 5 to 15 mol% in the light emitting polymer.

The number average molecular weight (M _n ) of the light emitting polymers obtained as described above is preferably about 1,500 to 10,000,000, more preferably about 10,000 to 1,000,000, and the polydispersity (PDI) is preferably about 1 to 50, More preferably, it is about 1.5-6.0

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 molecule is used as a material for forming 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 organic electroluminescent device of the present invention may be configured to further include 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 organic electroluminescent device composed of a substrate / anode / hole transport layer / light emitting layer / electron transport layer / cathode. Referring to this, an example of an organic electroluminescent device to which the organic electroluminescent molecule of the present invention is applied is as follows. It can be prepared 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 organic 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 ~ 200nm, the thickness of the hole transport layer and the electron transport layer is preferably 10 ~ 10,000Å.

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 a triazole derivative.

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, methacryl polymer, polybutyral, polyvinyl acetal, diallyl phthalate polymer, phenol resin, epoxy resin, Silicone resins, polysulfone resins or urea resins, and the like, which may be used individually or in combination.

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

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, and the like having a small work function are used.

The organic electroluminescent device according to the present invention may be manufactured in the order as described above, namely anode / hole transport layer / light emitting layer / electron transport layer / cathode, and vice versa, that is, cathode / electron transport layer / light emitting layer / hole transport layer / anode You may manufacture in order. It should be noted that such a laminated structure is exemplary and is not limited to a specific laminated structure of a light emitting device as long as the light emitting polymer provided in the present invention is used.

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 light conversion material in a photodiode or a semiconductor material in a polymer TFT (Thin Film Transistor).

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.

In the following Examples and Comparative Examples, the compounds referred to as S1 to S11 are each represented by the following structural formula as monomers for the production of light emitting polymers.

             S1 S2

S3 S4

S5 S6

S7 S8

S9 S10

S11

In addition, M1, M2 and M3 correspond to intermediate products in the process of manufacturing S6, S7, S9 and S11 in FIGS.

Preparation Example 1

Synthesis of monomer S6 according to the reaction mechanism shown in FIG. 2

a) synthesis of M1-2

50 g of M1-1 and 230 g of SOCl ₃ were added to 150 ml of methanol, followed by reaction for about 8 hours under reflux conditions. After the reaction, methanol and SOCl ₃ were removed through simple distillation to obtain 45 g of M1-2.

b) synthesis of M1-4

70 g of M1-3, 90 g of 2-ethylhexylbromide, 36 g of KOH, and 6 g of NaI were added to 250 ml of ethanol and reacted for 3 days under reflux conditions. After the reaction, the mixture was extracted using normal hexane, and then unreacted reactants were removed using column chromatography to obtain 95 g of M1-4.

c) synthesis of M1-5

After dissolving 50 g of M1-4 in 500 ml of methylene chloride, 1 equivalent of bromine was slowly added at 0 ° C. After reacting for 8 hours, the mixture was washed with distilled water, the solvent was removed by rotary evaporation, and M1-5 was obtained by vacuum distillation.

d) synthesis of M1-6

After 50 g of M1-5 was dissolved in 200 ml of ether, the temperature was lowered to −78 ° C. and 1 equivalent of a butyllithium 1.6M solution was slowly added. After reacting for 2 hours, 2 equivalents of triethylborate was injected. After reacting for 6 hours, 200 ml of HCl, 800 ml of distilled water, and ice were added to the mixed solution for 1 hour to obtain 25 g of M1-6.

 e) synthesis of M1-7

20 g of M1-6 and 12 g of M1-2 were dissolved in 200 ml of THF, and 80 ml of a 2M K ₂ CO ₃ aqueous solution was added, followed by bubbling with nitrogen. After 1 hour, 0.3 g of Pd (PPh ₃ ) ₄ was added and reacted under reflux for 8 hours. After the reaction, the solvent was removed by a rotary evaporator, extracted with methylene chloride, and then 14 g of M1-7 was obtained by column chromatography.

f) synthesis of M1-8

After dissolving 10 g of M1-7 in 50 ml of methylene chloride, 20 ml of SOCl ₂ was added at room temperature and reacted under reflux for 10 hours. After the reaction, the solvent was removed by simple distillation and extracted with methylene chloride. Then, after washing with 10 wt% NaOH solution, 6 g of M1-8 was obtained using column chromatography.

g) synthesis of M1-13

20 g of M1-12 was dissolved in 200 ml of methylene chloride, and then 1 equivalent of bromine was slowly added at 0 ° C. After reacting for 10 hours, the mixture was washed with distilled water and the solvent was removed using a rotary evaporator to obtain M1-13.

h) synthesis of M1-9

While heating 0.95 g of magnesium, a solution in which 10 g of M1-13 was dissolved in 200 ml of THF was slowly added thereto and reacted under reflux for 2 hours. After the reaction, the temperature was lowered to room temperature and M1-8 was added. After 2 hours, 100 ml of acetic acid was added and the ether component was removed using a rotary evaporator, followed by reaction for 8 hours at a temperature of 110 ° C. Then, the mixture was extracted with methylene chloride and 9g of M1-9 was obtained using column chromatography.

i) Synthesis of M1-10

After dissolving 9 g of M1-9 in 200 ml of benzene, the temperature was raised to 110 ° C., 0.1 g of BPO was added, followed by addition of 2 equivalents of NBS. After reacting for 3 hours, the temperature was lowered to room temperature, 300 ml of nucleic acid was added, and M1-10 was obtained by column chromatography.

j) synthesis of M1-11

10 g of triethylphosphite was injected into 5 g of M1-10, and the temperature was raised to 100 ° C. for 10 hours. After completion of the reaction, unreacted triethylphosphite was removed using vacuum distillation to obtain M1-11.

k) synthesis of S6

4.4 g of M1-11 and 1.9 g of 4-bromobenzaldehyde were dissolved in 200 ml of THF, and 2.2 equivalents of potassium tertary butoxide was added thereto, followed by reaction at room temperature for 8 hours. After the reaction, the solvent was removed using a rotary evaporator, extracted using methylene chloride, and washed with 1N hydrochloric acid and distilled water. After removing the solvent, 3.2 g of S6 was obtained using column chromatography using methylene chloride and hexane.

Preparation Example 2

Synthesis of monomer S9 according to the reaction mechanism shown in FIG. 3

a) synthesis of M2-1

After dissolving 9.5 g of M1-8 and 6.6 g of phenol in 30 ml of methylene chloride, 0.1 g of methanesulfonic acid and 3 g of 3-mercapto-propionic acid were added and the temperature was increased to 40 ° C. The reaction was carried out for 8 hours while maintaining. After completion of the reaction, the mixture was washed with distilled water and column chromatography was used to obtain 13g of M2-9.

b) synthesis of M2-2

13 g of M2-1 and 9 g of KOH were added to 100 ml of DMSO and mixed well, and then 12 g of bromo-2-methyl-butane was added thereto and reacted at room temperature for 10 hours. After completion of the reaction, 300 ml of distilled water was added, extracted with hexane, and 9.3 g of M2-2 was obtained by column chromatography.

c) synthesis of M2-3

After dissolving 9.3 g of M2-2 in 200 ml of benzene, 0.2 g of BPO and 5.4 g of NBS were added under reflux to react for 3 hours. After completion of the reaction, the temperature was cooled to room temperature, 300 ml of hexane was added and the column chromatography was used to contain the compound containing M2-3 (i.e., other unreacted or side reaction components including M2-3 in the form of impurities) State) 10.2 g was obtained.

d) synthesis of M2-4

10.2 g of compound containing M2-3 and 7 g of triethylphosphite were added to a reactor, and the temperature was raised to 100 ° C. for 10 hours. After completion of the reaction, unreacted triethylphosphite was removed using vacuum distillation to obtain M2-4.

e) synthesis of S9

10 g of M2-4 and 4.5 g of 4-bromo benzaldehyde were dissolved in 400 ml of THF, and 3.2 g of potassium-t-butoxide was added thereto, followed by reaction for 10 hours. After completion of the reaction, 5.5g of S9 was obtained by column chromatography.

Preparation Example 3

Synthesis of monomers S7 and S11 according to the reaction mechanism shown in FIG. 4

-Synthesis of S11

a) synthesis of M3-1

3.5 g (145 mmol) of Mg were placed in a 500 ml three-necked flask, followed by 60 g (145 mmol) of 9,9-dihexyl-2-bromofluorene in THF 300. It was dissolved in ml and slowly added dropwise to prepare a Grignard reagent. The bath temperature was lowered to 0 ° C. or lower, followed by addition of 39 g (102 mmol) of 2,7-dibromofluorenone (2,7-dibromofluorenone) under nitrogen stream, and the temperature was gradually raised to room temperature. Then it was stirred for 10 hours. The reaction was poured into water, the organic layer was separated and the solvent removed by rotary evaporator. 65 g (97 mmol, 83%) of compound 9- (9 ', 9'-dihexylfluorene-2'-yl) -2,7, -dibromofluorene- via separation using column chromatography 9-ol (9- (9,9-dihexylfluoren-2-yl) -2,7-dibromofluoren-9-ol; M3-1) was obtained.

b) synthesis of M3-2

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. , 53 g (473 mmol) of potassium-t-butoxide (t-BuOK) was added slowly, followed by reaction at 70 ° C. for 12 hours. The reaction was poured into 500 ml of water, extracted with methylene chloride, the solvent was removed with a rotary evaporator, separated by column chromatography using a mixed solvent of hexane and ethyl acetate, and then 1,2-di (2-methyl). 3 g (148 mmol, 81%) of butyloxy benzene (1,2-di (2-methyl) butyloxy benzene; M3-2) were obtained.

C) Synthesis of S11

In a 2-liter round flask, 45 g (67 mmol) of compounds M3-1 and 22.6 g (90 mmol) of M3-2 were dissolved in 500 mL of dichloromethane, and then the temperature was lowered to 0 ° C. and methanesulfonic acid was stirred. A solution of 7.5 g (78 mmol) of (methanesulfonic acid) dissolved in 100 ml of dichloromethane was slowly added thereto, followed by stirring for 2 hours. The reaction was poured into water, extracted with methylene chloride, the solvent was removed by rotary evaporator and separated using column chromatography. As a result, compound 2,7-dibromo-9- (9 ', 9'-dihexylfluorene-2'-yl) -9- (3 ", 4" -di (2 "-methyl) butyloxy Phenyl) fluorine (2,7-dibromo-9- (9 ', 9'-dihexylfluoren-2'-yl) -9- (3 ", 4 "-di (2" -methyl) butyloxyphenyl) fluorine; S11) 57 g (63 mmol, 94%) was obtained.

-Synthesis of S7

45 g (67 mmol) of the compound M3-1 and 67 g (200 mmol) of 9 ', 9'-dihexylfluorene were dissolved in 500 ml of dichloromethane in a round flask. The temperature was lowered to 0 ° C., and a solution of 7.5 g (78 mmol) of methanesulfonic acid dissolved in 100 ml of dichloromethane was slowly added while stirring, followed by stirring for 2 hours. The reaction was poured into water, extracted with methylene chloride, the solvent was removed by rotary evaporator, and separated by column chromatography to yield 2,7-dibromo-9,9-di- (9 ', 9'-di). Hexylfluorene-2'-yl) fluorene (2,7-dibromo-9 ', 9'-di- (9', 9'-dihexylfluoren-2'-yl) fluorene; S7) 33 g (33 mmol, 50 %) Was obtained.

Comparative Example 1

Into a 50 ml Schlenk flask, 0.89 mmol of compound S1, 0.87 mmol of compound S2, 0.11 mmol of compound S3 0.21 mmol, and 0.06 mmol of compound S5 were added, followed by 16.4 ml of toluene degassed with nitrogen. It was dissolved and stored under nitrogen atmosphere (monomer solution). 8.2 ml of toluene degassed with nitrogen by addition of 4.35 mmol of Ni (COD) ₂ , 4.35 mmol of 1.4-cyclooctadiene (COD), and 4.35 mmol of dipyridyl under a nitrogen atmosphere and 8.2 ml of DMF was added and then stirred at 80 ° C. for 30 minutes (catalyst solution). The monomer solution prepared above was then added to the catalyst solution vessel and polymerized for 24 hours. After the polymerization was completed, the reaction solution was added to 300 ml of hydrochloric acid (35% by weight): acetone: ethanol = 1: 1: 1 solution to remove the unreacted catalyst and precipitate the 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 dried (M _w : 94,000, Mn: 40,700, PDI: 2.31).

Example 1

Into a 50 ml Schlenk flask, 0.80 mmol of compound S1, 0.80 mmol of compound S2, 0.21 mmol of compound S3, 0.10 mmol of compound S4, 0.06 mmol of compound S5, 0.14 mmol of compound S6, and then degassed with nitrogen. It was dissolved in 16.4 ml of embodied toluene and stored under nitrogen atmosphere (monomer solution). As a catalyst, 4.35 mmol of Ni (COD) ₂ , 4.35 mmol of 1.4-cyclooctadiene (COD), and 4.35 mmol of dipyridyl were added to a Schlenk flask under a nitrogen atmosphere, and 8.2 ml of toluene degassed with nitrogen. And 8.2 mL of DMF were added and then stirred at 80 ° C. for 30 minutes (catalyst solution). The monomer solution prepared above was added to the catalyst solution vessel and polymerized for 24 hours. After the polymerization was completed, the reaction solution was added to 300 ml of hydrochloric acid (35% by weight): acetone: ethanol = 1: 1: 1 solution to remove the unreacted catalyst and precipitate the 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 dried (M _w : 76,100, Mn: 34,600, PDI: 2.2).

Example 2

Into a 50 mL Schlenk flask, 0.607 mmol of compound S7, 0.067 mmol of compound S6, and 0.027 mmol of compound S5 were dissolved in 7.3 mL of toluene degassed with nitrogen, and then stored under nitrogen atmosphere (monomer solution). . As a catalyst, 1.42 mmol of Ni (COD) ₂ , 1.42 mmol of 1.4-cyclooctadiene (COD), and 1.42 mmol of dipyridyl were added to a Schlenk flask under a nitrogen atmosphere, and 3.6 ml of toluene degassed with nitrogen. And 3.6 ml of DMF were added and then stirred at 80 ° C. for 30 minutes. (Catalyst solution) The monomer solution prepared above was added to the catalyst solution vessel and polymerized for 24 hours. After the polymerization was completed, the reaction solution was added to 300 ml of hydrochloric acid (35% by weight): acetone: ethanol = 1: 1: 1 solution to remove the unreacted catalyst and precipitate the 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 dried (M _w : 42,500, Mn: 19,300, PDI: 2.2).

Comparative Example 2

Into a 50 ml Schlenk flask, 0.607 mmol of compound S7, 0.067 mmol of compound S8, and 0.027 mmol of compound S5 were dissolved in 7.1 ml of toluene degassed with nitrogen, and then stored under nitrogen atmosphere (monomer solution). . As a catalyst, 1.42 ml of Ni (COD) ₂ , 1.42 ml of 1.4-cyclooctadiene (COD) and 1.42 ml of dipyridyl were added to a Schlenk flask under nitrogen atmosphere and 3.5 ml of toluene degassed with nitrogen and DMF 3.5 ml were added and then stirred at 80 ° C. for 30 minutes (catalyst solution). The monomer solution prepared above was added to the catalyst solution vessel and polymerized for 24 hours. After the polymerization was completed, the reaction solution was added to 300 ml of hydrochloric acid (35% by weight): acetone: ethanol = 1: 1: 1 solution to remove the unreacted catalyst and precipitate the 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 dried (M _w : 48,800, Mn: 20,300, PDI: 2.4).

Example 3

Into a 50 ml Schlenk flask, 0.160 g (0.162 mmol) of Compound S7, 0.331 g (0.378 mmol) of Compound S11, 0.066 g (0.067 mmol) of Compound S9 and 0.048 g (0.067 mmol) of Compound S10 were added. After silver, it was dissolved in 6 ml of toluene degassed with nitrogen, and then stored under nitrogen atmosphere (monomer solution). 0.430 g (1.531 mmol) of Ni (COD) _2, 0.107 g (0.977 mmol) of 1.4-cyclooctadiene (COD), and 0.245 g (1.550 mmol) of dipyridyl in a Schlenk flask 24 ml of toluene degassed with nitrogen and 6 ml of DMF were added, followed by stirring at 80 ° C. for 30 minutes (catalyst solution). The monomer solution prepared above was added to the catalyst solution container, reacted for 150 hours, 1 ml of bromobenzene was added, and then reacted for 24 hours. After the reaction was completed, the reaction solution was added to 200 ml of hydrochloric acid (35 wt%): acetone: ethanol = 1: 1: 1 solution to remove the unreacted catalyst and precipitate the 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 (M _w : 132,000, Mn: 47,100, PDI: 2.8) .

Example 4

Fabrication of Electroluminescent Device

To form a hole injection layer on top of a patterned indium-tin oxide (ITO) substrate, H. C. Stark's trade name Baytron AI4083 was spin coated at 2000 pm and then dried at 100 ° C. for 5 minutes. Then, the polymer synthesized in Examples and Comparative Examples was coated with a solution (0.5 to 2% by weight) dissolved in toluene to form a light emitting layer having a thickness of 600 to 1000 Pa. LiF 20 kV was vacuum deposited on the light emitting layer, and Al 1000 kV was vacuum deposited to fabricate an organic electroluminescent device. The characteristics test of the fabricated organic electroluminescent device was measured using McScience's Polaronix IVL tester and Minolta's CS1000 and LS100, and the results are shown in Table 1 below. In Example 2 and Comparative Example 2, FIG. More specific results are shown.

division Start voltage (V) Efficiency (㏅ / A) Color coordinates (x, y) Comparative Example 1 5.0 0.36 0.18, 0.21 Example 1 5.8 0.48 0.17, 0.19 Comparative Example 2 5.8 1.77 0.16, 0.25 Example 2 6.4 0.96 0.16, 0.14 Example 3 6.0 3.90 0.17, 0.24

As can be seen from the table, the test results for the polymer polymerized using the monomers S1, S2, S3, S4 and S5 (Comparative Example 1) and the polymer polymerized using S6 as a monomer (Example 1) In light of this, it was confirmed that the introduction of S6 into the polymer backbone showed the improvement of all physical properties such as color coordinates, external quantum efficiency, and highest luminance.

On the other hand, in view of the test results for the case where S8 was introduced into the polymer main chain (Comparative Example 2) and the case where S6 was introduced (Example 2), although both S6 and S8 had a distyrenylbenzene residue introduced into the main chain, There is a big difference in color purity.

That is, as shown in Figure 5, the maximum peak of the electroluminescence spectrum for the electroluminescent device fabricated using the electroluminescent molecules of Example 2 was 460 nm blue emission region, the dull peak was hardly appeared, The narrow wavelength band showed high color purity. On the other hand, the electroluminescent device manufactured using the electroluminescent adsorption molecule of Comparative Example 2, according to the above table seems to be excellent in terms of external quantum efficiency and the highest efficiency, which is a general phenomenon that appears when the color purity is out of blue 5 As can be seen from the broad wavelength band compared to Example 2, it can be seen that there is a problem in the implementation of high color purity. Therefore, Comparative Example 2 is not suitable for the purpose of blue light emission and considering the color purity it can be seen that Example 2 has a better performance.

In addition, the polymer (Example 3) synthesized using S7, S9, S10 and S11 as the monomer was improved by using a hole transporting material to improve the hole injection and transport ability, thereby showing a very good light emission characteristics.

In view of the above results, it can be seen that a form in which a substituent which prevents an excimer is fused to the distithybenzene moiety is useful for high purity blue light emission.

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 have disadvantages of light-emitting polymers having conventional distyrylbenzene moieties. (E.g., low color purity, etc.) can be remarkably improved to be used as a host material (especially a blue host material) such as blue, green and red of the electroluminescent device, thereby exhibiting excellent luminescence properties.

Simple modifications and variations of the present invention can be readily used by those skilled in the art, and all such variations or modifications can be considered to be included within the scope of the present invention.

Claims (8)

Distyrylbenzene derivatives for the preparation of organic electro-molecular advertising molecules represented by the following structural formula 1 or formula 2: Structural Formula 1

Structural Formula 2

In the above, R ₁ to R ₁₈ are each independently 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 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; 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; Substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms; Substituted or unsubstituted arylsilyl group having 3 to 40 carbon atoms; Substituted or unsubstituted carbazole groups having 12 to 60 carbon atoms; Substituted or unsubstituted phenothiazine group having 6 to 60 carbon atoms; Or a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; And X ₁ , X ₂ , X ₃ and X ₄ are each independently Cl, Br, I, B (OH) ₂ ,

or

being. An organic bald molecule comprising at least one of residues each derived from the compounds of Formulas 1 and 2 according to claim 1 as monomers and represented by the following Formula 3: Structural Formula 3

In the above, R ₁ to R ₁₈ are each independently 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 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; 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; Substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms; Substituted or unsubstituted arylsilyl group having 3 to 40 carbon atoms; Substituted or unsubstituted carbazole groups having 12 to 60 carbon atoms; Substituted or unsubstituted phenothiazine group having 6 to 60 carbon atoms; Or a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; Ar is selected from the group consisting of a substituted or unsubstituted aromatic compound having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaromatic compound having 2 to 60 carbon atoms, and a combination thereof; l and m are each an integer of 0 to 1,000, except that both l and m become 0; n is an integer from 1 to 20,000; And p is an integer from 0 to 10,000. The method according to claim 2, wherein R ₁ to R ₁₈ is an organic baler molecule, characterized in that selected from the group: Hydrogen,

In the above, R ₁₉ and R ₂₀ are each independently a linear or branched alkyl group having 1 to 20 carbon atoms, R ₂₁ is hydrogen, a linear or branched alkyl, alkoxy or trialkylsilyl group having 1 to 20 carbon atoms, R ₂₂ and R ₂₃ are each independently a linear or branched alkyl group having 1 to 20 carbon atoms, R ₂₄ , R ₂₅ and R ₂₆ are each independently 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, R ₂₇ , R ₂₈ , R ₂₉ , R ₃₀ , R ₃₁ and R ₃₂ are each independently 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, X is O or S, Y and Z are N, and a is an integer of 1-3. According to claim 2, wherein the R ₇ and R ₁₆ is an organic baling molecule, characterized in that selected from the group: Hydrogen,

According to claim 2, wherein the Ar is an organic baler molecule, characterized in that selected from the group: (Iii) a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; (Ii) a substituted or unsubstituted heterocyclic arylene group having 2 to 60 carbon atoms in which 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 substituted or unsubstituted arylenevinylene group having 6 to 60 carbon atoms; (Iii) a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; (Iii) a substituted or unsubstituted carbazole group having 12 to 60 carbon atoms; And (Iii) combinations thereof; In the above, 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 silyl groups. [Claim 3] According to claim 2, wherein the number average molecular weight of the organic baler molecule is 1,500 to 10,000,000, the molecular weight distribution is characterized in that the organic baler molecule. An organic electroluminescent device comprising at least one layer comprising an organic electroluminescent molecule according to claim 2 between an anode and a cathode, said layer being a hole transport layer, a light emitting layer, an electron transport layer or a hole blocking layer. The organic electroluminescent device according to claim 7, wherein the structure of the electroluminescent device is an anode / light emitting layer / cathode, an anode / hole transporting layer / light emitting layer / cathode, or an anode / hole transporting layer / light emitting layer / electron transporting layer / cathode.

Images