KR20140046541A - Novel organic electroluminescence compounds and organic electroluminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same. The organic electroluminescent compound according to the present invention improves thermal stability, enhances luminance and lifetime properties when compared with the existing materials. Moreover, the organic electroluminescent compound according to the present invention provides an OLED element with low drive voltage and improved current efficiency and operation lifetime.

Description

TECHNICAL FIELD The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the organic electroluminescent compound,

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device comprising the same.

Among display devices, an electroluminescence device (EL device) is a self-luminous display device having a wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak Company first developed an organic EL device using an aromatic diamine and an aluminum complex having a low molecular weight as a material for forming a light emitting layer (Appl. Phys. Lett. 51, 913, 1987].

The most important factor for determining the luminous efficiency in the organic EL device is the luminescent material. As a luminescent material, a fluorescent luminescent material has been widely used, but the development of a phosphorescent luminescent material has been widely carried out in view of the fact that the phosphorescent luminescent material on the mechanism of electroluminescence can improve the luminescent efficiency by the theoretical four times as compared with the fluorescent luminescent material . Until now, the iridium (III) complex series has been widely known as a phosphorescent light emitting material, and each of R, G and B has (acac) Ir (btp) ₂ (bis (2- (2'-benzothienyl) -pyridinate- 3 ') iridium (acetylacetonate)), Ir (ppy) ₃ (tris (2-phenylpyridine) iridium) and Firpic (bis (4,6-difluorophenylpyridinate- Collisional iridium) and the like are known.

The light emitting material may also be used as a dopant / host material system in which a host material and a dopant are mixed to improve color purity, luminous efficiency and stability. When using such a system, the selection is important because the host material greatly affects the efficiency and performance of the light emitting device. In the prior art, 4,4'-bis (carbazol-9-yl) biphenyl (CBP) is the most widely known phosphorescent host material. In recent years, Pioneer, etc., of Japan, have been using bathocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenyl phenolate) Balq) as a host material to develop a high-performance organic EL device.

However, the conventional phosphorescent host materials are advantageous from the viewpoint of luminescence characteristics, but they have the following disadvantages: (1) the material is changed when the glass transition temperature is low and the thermal stability is low and the high temperature deposition process is performed under vacuum . (2) Since the power efficiency = [(π / voltage) x current efficiency] in the organic EL device, the power efficiency is inversely proportional to the voltage. However, the organic EL device using the phosphorescent host material has a higher current efficiency (cd / A) than the organic EL device using the fluorescent material, but the driving voltage is also very high, so there is no great advantage in terms of power efficiency (lm / w) . (3) In addition, when used in an organic EL device, it is unsatisfactory in terms of operating life, and luminous efficiency is still required to be improved.

Generally, in order to produce a product in the production of an OLED panel, since the organic material layer is exposed to the deposition condition of the production line for a long time, the thermal stability of the material is essential for commercialization of the organic material. Particularly, even in the case of a material having excellent performance as an organic material used in an organic electroluminescent device, there is a problem that a pyrolysis phenomenon occurs when it is exposed to a high temperature for a long time in a manufacturing process

Korean Patent No. 10-0957288 discloses a carbazole derivative as an organic electroluminescent compound. Korean Patent No. 10-0948700 discloses an arylcarbazole derivative as an organic electroluminescent compound. Korean Patent Laid-Open Publication No. 2008-0080306 discloses (di) benzothienes or (di) benzofuran derivatives as compounds for organic electroluminescence devices. However, organic EL devices including the compounds disclosed in the above documents are still unsatisfactory in terms of power efficiency, luminous efficiency, life span, and the like.

Korean Patent No. 10-0957288 (May 12, 2010) Korean Patent Publication No. 2008-0080306 (September 3, 2008) Korean Patent No. 10-0948700 (March 12, 2010)

Accordingly, an object of the present invention is to provide an organic electroluminescent compound having excellent thermal stability and higher luminescent efficiency and device life than existing materials in order to solve the above problems, and secondly, And to provide a highly efficient and long-life organic electroluminescent device as a material.

As a result of intensive studies to solve the above technical problems, the present inventors have found that an organic electroluminescent compound represented by the following general formula (1) achieves the above-mentioned object and completed the present invention.

[Chemical Formula 1]

In Formula 1,

L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (3-30 membered heteroarylene, or substituted or unsubstituted (C6-C30) arylene;

X ₁ And X ₂ Are each independently CH or N;

Y is -O-, -S-, -CR ₁₁ R ₁₂ -or -NR _13- ;

Ar ₁ is substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;

Ar ₂ is hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;

R ₁ to R ₃ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, Substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (5-7 membered) heterocycloalkyl, _{NR 14 R 15, -SiR 16 R} 17 R 18, -SR 19, -OR 20, cyano, nitro or hydroxyl, or a monocyclic or polycyclic with an adjacent substituent via (C5-C30) cycloaliphatic or aromatic ring And the carbon atom of the alicyclic or aromatic ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;

R ₁₁ to R ₂₀ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted (C5-C30) cycloaliphatic or heteroaryl, together with the adjacent substituents, are optionally substituted with one or more substituents independently selected from the group consisting of (C5-C30) cycloalkyl, substituted or unsubstituted And the carbon atom of the alicyclic or aromatic ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;

a and c are each independently an integer of 1 to 4, and when a or c is an integer of 2 or more, each R ₁ or each R ₃ may be the same or different;

b is an integer of 1 to 3, and when b is an integer of 2 or more, each R ₂ may be the same or different;

The heteroarylene, heterocycloalkyl and heteroaryl comprise at least one heteroatom selected from B, N, O, S, P (= O), Si and P.

The organic electroluminescent compound according to the present invention has excellent thermal stability, good luminescent properties and excellent lifetime characteristics. Further, the device fabricated from the organic electroluminescent compound according to the present invention provides an OLED device having a low driving voltage and improved current efficiency and operating life.

Hereinafter, the present invention will be described in more detail, but this is for explanation and should not be construed as a method of limiting the scope of the present invention.

The present invention relates to an organic electroluminescent compound represented by Formula 1, an organic electroluminescent material including the organic electroluminescent compound, and an organic electroluminescent device comprising the material.

The organic electroluminescent compound represented by Formula 1 of the present invention will be described in more detail as follows.

In Formula 1, preferably, L ₁ and L ₂ are each independently a single bond, a substituted or unsubstituted (3-15 member) heteroarylene, or a substituted or unsubstituted (C 6 -C 15) arylene ;

X ₁ And X ₂ is Each independently CH or N;

Y is -O-, -S- or -CR ₁₁ R ₁₂ -;

Ar ₁ is substituted or unsubstituted (C 6 -C 15) aryl, or substituted or unsubstituted (3-15 member) heteroaryl;

Ar ₂ is hydrogen, substituted or unsubstituted (C6-C15) aryl, or substituted or unsubstituted (3-15 membered) heteroaryl;

R ₁ to R ₃ are each independently hydrogen, substituted or unsubstituted (C 6 -C 15) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, or together with the adjacent substituents, a single or multiple (C5- C30) alicyclic or aromatic ring, and the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;

a to c are integers of 1 or 2;

In Formula 1, more preferably, L ₁ and L ₂ are each independently a single bond, unsubstituted (3-10 membered heteroarylene, or substituted or unsubstituted (C6-C10) arylene;

X ₁ And X ₂ is Each independently CH or N;

Y is -O- or -S-;

Ar ₁ is substituted or unsubstituted (C 6 -C 10) aryl, or substituted (3-15 member) heteroaryl;

Ar ₂ is hydrogen, substituted or unsubstituted (C6-C15) aryl, or substituted (3-15 membered) heteroaryl;

R ₁ to R ₃ are each independently hydrogen or substituted or unsubstituted (C 6 -C 10) aryl or may form a monocyclic or polycyclic (C 5 -C 30) alicyclic or aromatic ring together with the adjacent substituents, The carbon atom of the alicyclic or aromatic ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;

a to c are integers of 1;

The "(C1-C30) alkyl" described in the present invention means straight chain or branched chain alkyl having 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the like. As used herein, "(C2-C30) alkenyl" means a straight or branched chain alkenyl having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. As used herein, " (C2-C30) alkynyl " means straight or branched chain alkynyl having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms. Examples of the alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl and 1-methylpent-2-onyl. As used herein, "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms, preferably 3 to 20 carbon atoms, more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. As used herein, the term "(C6-C30) cycloalkylene" refers to a cycloalkyl group having 6 to 30 carbon atoms in which one hydrogen atom has been removed, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms . As used herein, “(3-7 membered) heterocycloalkyl” has 3 to 7 ring skeleton atoms, and at least one heteroatom selected from the group consisting of B, N, O, S, P (═O), Si and P, Preferred are cycloalkyls comprising at least one heteroatom selected from O, S and N, for example tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. The term "(C6-C30) cycloalkylene" as used herein means a single ring or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, wherein the number of carbon atoms in the ring is 6 to 20, 15 is more preferable. Examples of such aryls include phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, , Fluoranthenyl, and the like. As used herein, “(3- to 30-membered) heteroaryl (ene)” has 3 to 30 ring skeleton atoms, and at least one hetero selected from the group consisting of B, N, O, S, P (═O), Si and P It means an aryl group containing an atom. Here, the number of the atoms of the ring skeleton is preferably 5 to 20, more preferably 5 to 15. The number of heteroatoms is preferably 1 to 4, and may be a monocyclic ring system or a fused ring system condensed with at least one benzene ring, and may be partially saturated. In addition, the heteroaryl (phenylene) also includes a heteroaryl group in which at least one heteroaryl or aryl group is linked to a heteroaryl group by a single bond. Examples of such heteroaryls include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl Monocyclic heteroaryl such as triazolyl, tetrazolyl, furanzyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like; Benzothiazolyl, benzooxazolyl, isoindolyl, benzothiazolyl, benzothiazolyl, benzooxazolyl, isoindolyl, benzothiazolyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, , Fused ring heteroaromatic rings such as indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxaphyl, phenanthridinyl, benzodioxolyl and the like Aryl and the like. "Halogen" herein includes F, Cl, Br and I atoms.

Also, in the term "substituted or unsubstituted" described in the present invention, "substituted" means that a hydrogen atom is replaced by another atom or another functional group (ie, a substituent) in a certain functional group. Substituted in the general formula (I) of L _1, L _2, Ar _1, Ar _2, R ₁ to R _3, and R ₁₁ to R ₂₀ alkyl, substituted aryl (alkylene), substituted heteroaryl (alkylene), substituted cycloalkyl (alkylene (C6-C30) aryl, (C6-C30) aryl optionally substituted by deuterium, halogen, halogen, (C1-C30) (C3-C30) cycloalkyl, (5-7 membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, N-carbamoyl, (C6-C30) arylamino, di (C6-C30) arylamino, di (C6- (C6-C30) aryl, (C6-C30) aryl (C1-C30) , Nitro and hydroxy Means that at least one selected from the group consisting of.

The organic electroluminescent compound according to the present invention can be more specifically exemplified by the following compounds.

The organic electroluminescent compound according to the present invention can be prepared as shown in Reaction Scheme 1 below.

[Reaction Scheme 1]

In the above Reaction Scheme 1, Ar ₁ , Ar ₂ , L ₁ , L ₂ , Y, X ₁ , X ₂ , R ₁ to R ₃ , a, b and c are as defined in Formula .

The present invention also provides an organic electroluminescent material comprising an organic electroluminescent compound of Formula 1 and an organic electroluminescent device comprising the same. The material may be composed of the organic electroluminescent compound of the present invention alone, and may further include conventional materials included in the organic electroluminescent material. An organic electroluminescent device according to the present invention includes a first electrode; A second electrode; And at least one organic compound layer interposed between the first electrode and the second electrode, wherein the organic compound layer comprises at least one organic electroluminescent compound represented by Formula 1.

One of the first electrode and the second electrode may be an anode and the other may be a cathode. The organic material layer may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer and a hole blocking layer.

The organic electroluminescent compound of Formula 1 of the present invention may be included in the light emitting layer. When used in the light emitting layer, the organic electroluminescent compound of Formula 1 of the present invention may be included as a host material. Preferably, the light emitting layer may further include at least one dopant, and if necessary, a compound other than the organic electroluminescent compound of Formula 1 of the present invention may be further included as a second host material.

The second host material may be any known phosphorescent host, but is preferably selected from the group consisting of compounds represented by the following formulas (2) to (4) in view of luminous efficiency.

(2)

_{H- (Cz-L 4) h} -M

(3)

H- (Cz) _i -L ₄ -M

[Chemical Formula 4]

In the above Chemical Formulas 2 to 4,

Cz has the following structure,

R ₂₁ to R ₂₄ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted Heteroaryl or R ₂₅ R ₂₆ R ₂₇ Si-, R ₂₅ to R ₂₇ are each independently substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 6 -C 30) aryl; L ₄ is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5-30 membered) heteroarylene; M is a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl; Y ₁ and Y ₂ are -O-, -S-, -N (R ₃₁ ) -, -C (R ₃₂ ) (R ₃₃ ) -, and Y ₁ and Y ₂ are not simultaneously present; R ₃₁ to R ₃₃ each independently represent a substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 W) heteroaryl ring, R ₃₂ And R ₃₃ may be the same or different; each of h and i is independently an integer of 1 to 3, j, k, l and m are each independently an integer of 0 to 4, and when h, i, j, k, l or m is an integer of 2 or more, (Cz-L ₄ ), each (Cz), each R ₂₁ , each R ₂₂ , each R _23, or each R ₂₄ may be the same or different.

Specifically, preferred examples of the second host material are as follows.

As the dopant used in the organic electroluminescent device of the present invention, at least one phosphorescent dopant is preferable. The phosphorescent dopant material to be applied to the organic electroluminescent device of the present invention is not particularly limited, but is preferably a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) , An iridium (Ir), an osmium (Os), a copper (Cu) and a platinum (Pt) are more preferable, and an orthometallated iridium complex compound is even more preferable.

It is preferable that the phosphorescent dopant is selected from the group consisting of compounds represented by the following Chemical Formulas (5) to (7).

[Chemical Formula 5] < EMI ID =

In Formulas 5 to 7, L is selected from the following structures;

R ₁₀₀ is hydrogen, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 3 -C 30) cycloalkyl; R ₁₀₁ to R ₁₀₉ And R ₁₁₁ To R < ₁₂₃ > are each independently selected from the group consisting of hydrogen, deuterium, halogen, (C1-C30) alkyl substituted or unsubstituted with halogen, substituted or unsubstituted (C3-C30) cycloalkyl, cyano, C1-C30) alkoxy; R ₁₂₀ to R ₁₂₃ are adjacent substituents connected to each other to form a fused ring, for example, quinoline formation is possible; R ₁₂₄ to R ₁₂₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 1 -C 30) aryl; When R ₁₂₄ to R ₁₂₇ are aryl groups, the adjacent groups are connected to each other to form a fused ring, for example, fluorene formation is possible; R ₂₀₁ To R < ₂₁₁ > are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl substituted or unsubstituted with halogen or substituted or unsubstituted (C3-C30) cycloalkyl; f and g are each independently an integer of 1 to 3, and when f or g is an integer of 2 or more, each R ₁₀₀ may be the same or different from each other; n is an integer of 1 to 3;

Specific examples of the phosphorescent dopant material are as follows.

The present invention further provides a material for manufacturing an organic electroluminescent device in a further aspect. The material comprises a first host material and a second host material, and the first host material may comprise a compound of the present invention.

Wherein the weight ratio of the first host material to the second host material may range from 1:99 to 99: 1.

Further, the organic electroluminescent device of the present invention includes a first electrode; A second electrode; And at least one organic material layer sandwiched between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, the light emitting layer includes a material for an organic electroluminescence device of the present invention and a phosphorescent dopant material, The material for the electroluminescent device is used as a host material.

In the organic electroluminescent device of the present invention, the organic material layer includes the organic electroluminescent compound of Formula 1, and at the same time, may include at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound.

Further, in the organic electroluminescent device of the present invention, in addition to the organic electroluminescent compound of Formula 1, an organic electroluminescent compound of the group 1, 2, 4, 5 period transition metal, lanthanide series and d- The organic compound layer may further include at least one metal or complex compound selected from the group consisting of a light emitting layer and a charge generating layer.

In addition, the organic electroluminescent device of the present invention can emit white light by including at least one light emitting layer containing a blue, red or green light emitting compound known in the art, in addition to the organic electroluminescent compound of the present invention. Further, if necessary, it may further include a yellow or orange light emitting layer.

In the organic electroluminescent device of the present invention, one layer (hereinafter referred to as a " surface layer ") of a chalcogenide layer, a metal halide layer and a metal oxide layer is formed on at least one inner surface of a pair of electrodes ) Or more. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferable examples of the chalcogenide include SiO _X (1? _X ? 2), AlO _x (1? _X ? 1.5), SiON or SiAlON. Preferred examples of the halogenated metal include LiF, MgF ₂ , CaF ₂ , Rare-earth metals, etc. Preferred examples of the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO and the like.

In the organic electroluminescent device of the present invention, it is also preferable to arrange a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transport compound and the oxidative dopant on at least one surface of the pair of electrodes thus fabricated . In this way, since the electron transfer compound is reduced to an anion, it becomes easy to inject and transport electrons from the mixed region to the light emitting medium. Further, since the hole transporting compound is oxidized and becomes a cation, it becomes easy to inject and transport holes from the mixed region into the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Further, a white organic electroluminescent device having two or more light emitting layers can be manufactured using a reductive dopant layer as a charge generation layer.

The formation of each layer of the organic electroluminescent device of the present invention can be performed by a dry film formation method such as vacuum deposition, sputtering, plasma or ion plating, or a wet film formation method such as spin coating, dipping or flow coating.

In the case of the wet film formation method, a thin film is formed by dissolving or dispersing a material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane, and any solvent may be used.

Hereinafter, the organic electroluminescent compound according to the present invention, the method for producing the same, and the luminescent characteristics of the device will be described with reference to the representative compound of the present invention for a detailed understanding of the present invention.

[Example 1] Preparation of Compound H-2

Preparation of Compound 1-1

(29.5 mmol) of 1-bromo-2-nitrobenzene, 7 g (35.4 mmol) of [1,1'-biphenyl] -4-ylboronic acid, tetrakis (triphenylphosphine) 1.1 g (0.88 mmol) of PPh ₃ ) ₄ and 7.8 g (73.7 mmol) of Na ₂ CO ₃ were added to 160 ml of toluene, 40 ml of ethanol and 40 ml of distilled water, and the mixture was stirred at 120 ° C for 5 hours. After the stirring was completed, the purified water was slowly added thereto to terminate the reaction. The reaction mixture was cooled to room temperature and extracted with distilled water and methylene chloride (MC). The organic layer was concentrated and then separated into a column [MC / hexane (Hex)] to obtain a compound 1-1, 7.1 g (87%).

Preparation of Compound 1-2

Compound 1-1 (7.1 g, 25.6 mmol) was dissolved in 65 mL of triethylphosphite and stirred at 140 ° C for 12 hours. To give the 2, 5.0g (80%) - After stirring was completed, was solidified by extracting the solvent, the die was recrystallized with chlorobenzene compound 1.

Preparation of compounds 1-3

Dibenzo [b, d] thiophene-4 Daily acid (50g, 219mmol), 2,4- dichloropyrimidine (42.4g, 284.7mmol), Pd ( PPh 3) 4 (7.6g, 6.58mmol), K ₂ CO ₃ (75.67 g, 547.5 mmol), H ₂ O (220 mL), ethanol (EtOH) (180 mL) and toluene (440 mL) were added and stirred at reflux for 2 hours. When the reaction was completed, the reaction mixture was cooled and solidified by adding MeOH. The resulting solid was columned on silica gel to give 35 g (54%) of compound 1-3.

Preparation of Compound H-2

The compound 1-3, 5.9g (0.020mol), Compound 1-2, 7g (0.018mol), 1.1g (0.028mol) of NaH and 350ml of dimethylformamide (DMF) were added and stirred at room temperature for 5 hours. After completion of the reaction, the reaction mixture was washed with distilled water and the resulting solid was purified by column to obtain 5.3 g (59%) of Compound H-2.

[Example 2] Preparation of Compound H-4

Preparation of Compound 2-1

(0.196 mol) of 2,4,6-trichloropyrimidine, 15 g (0.123 mol) of phenylboronic acid and 842 mg (0.0012 mol) of dichlorobis (triphenylphosphane) palladium (II) [PdCl ₂ (PPh ₃ ) ₂ ] 19.5 g (0.184 mol) of Na ₂ CO ₃ and 125 mL of H ₂ O were added, and 300 mL of ethylene glycol dimethyl ester was added thereto. The mixture was heated to 80 ° C and stirred for 12 hours. After completion of the reaction, the reaction mixture was washed with distilled water and extracted with EA. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure to obtain 20 g (71%) of compound 2-1.

Preparation of Compound 2-2

Compound 2-1, 10g (0.044mol), 4- di-benzothiophene boronic acid 11.6g (0.051mol), Pd (PPh 3) 4 1.5g (0.0013mol), K 2 CO 3 (2M) 44mL , and 20mL EtOH , 170 mL of ethylene glycol dimethyl ester was added, and the mixture was heated to 110 DEG C and stirred for 3 hours. After the reaction was completed, the reaction mixture was washed with distilled water and extracted with ethyl acetate (EA). The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator to obtain a column 2-2, 14g (85%).

Preparation of compound H-4

5 g (0.020 mol) of the compound 2-2, 7 g (0.018 mol) of the compound 1-2, 1.1 g (0.028 mol) of NaH and 350 mL of DMF were added and the mixture was stirred at room temperature for 5 hours. After the reaction was completed, the reaction mixture was washed with distilled water and the resulting solid was purified by column to obtain 4.5 g (41%) of Compound H-4.

[Example 3] Preparation of Compound H-9

Preparation of Compound 3-1

Biphenyl-3-Daily acid (20g, 101mmol), 1- bromo-4-iodobenzene (31.4g, 111mmol), Pd ( PPh 3) 4 (3.5g, 3mmol), K 2 CO 3 (28g, , Toluene (300 ml), EtOH (100 ml) and H ₂ O (100 ml) were placed, and the mixture was stirred under reflux. After 13 h, the mixture was extracted with dichloromethane (DCM) and H ₂ O, the DCM layer was dried over MgSO ₄ and filtered. The obtained solid was dissolved in CHCl _{3, and the product} was subjected to column chromatography with silica gel to obtain 26.37 g (84%) of Compound 3-1.

Preparation of Compound 3-2

Compound 3-1 (26.37 g, 96.2 mmol) and tetrahydrofuran (THF) (200 mL) were added and cooled to -78 ^° C. 2.5 M n-butyllithium (46 mL, 115 mmol) was added, and 1 hour later, isopropyl borate (33.3 mL, 144 mmol) was added. After 17 hours, the mixture was extracted with EA and H ₂ O and the EA layer was dried with MgSO ₄ . The EA layer was concentrated to give 15.1 g (59%) of compound 3-2.

Preparation of compound 3-3

Compound 3-2 (15g, 54.7mmol), 2- bromo-nitrobenzene (10.03g, 49.7mmol), Pd ( PPh 3) 4 2.0g (1.63mmol) and Na ₂ CO ₃ 14.5g (136.7mmol) in toluene 300 mL of ethanol, 75 mL of ethanol and 75 mL of distilled water, and the mixture was stirred at 120 DEG C for 5 hours. After the stirring was completed, the purified water was slowly added thereto to terminate the reaction. The reaction mixture was cooled to room temperature and extracted with distilled water and MC. The organic layer was concentrated and then separated into a column (MC / Hex) 3-3, 14.2 g (81%).

Preparation of compound 3-4

Compound 3-3 (15.67 g, 44.6 mmol), triethylphosphite [P (OEt) ₃ ] (100 mL) and 1,2-dichlorobenzene (1,2-DCB) (50 mL) were added and stirred under reflux. After 13 hours, the solvent was distilled off and dissolved in CHCl ₃ and columned with silica gel to give compound 3-4, 7.06 g (50%).

Preparation of Compound H-9

Compound 3-4 (5.6 g, 17.6 mmol), Compound 1-3, 5.9 g (20 mmol), 1.1 g (28 mmol) of NaH and 350 mL of DMF were added and stirred at room temperature for 5 hours. After the reaction was completed, the reaction mixture was washed with distilled water and the resulting solid was purified by column to obtain 3.4 g (33%) of Compound H-9.

[Example 4] Preparation of Compound H-22

Preparation of Compound 4-1

2,5-dibromo-nitrobenzene (30g, 106.80mmol), phenylboronic acid (15g, 128.16mmol), Pd ( PPh 3) 4 6.4g of (5.33mmol) and 2M Na ₂ CO ₃ 200mL of toluene and 530mL of ethanol And the mixture was refluxed at 120 ° C for 5 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residue was dried with magnesium sulfate. The organic layer was dried and separated into a column (4-1, 16g, 55%).

Preparation of Compound 4-2

Compound 4-1 (16 g, 57.53 mmol) and t-butylphenylboronic acid (12.8 g, 69.04 mmol) were synthesized in the same manner as compound 4-1 to give 19.2 g (96%) of compound 4-2.

Preparation of Compound 4-3

Compound 4-2 (19 g, 57.33 mmol) was dissolved in 190 mL of triethylphosphate and refluxed at 150 ° C for 6 hours. After the reaction was completed, the reaction mixture was distilled and then triturated with methanol (MeOH) to obtain 11.5 g (68%) of compound 4-3.

Preparation of Compound H-22

Compound H-22, 1 g (14%) was obtained by the same method as Compound H-2, using Compound 4-3, 3.9 g (13.03 mmol) and Compound 1-3, 4.3 g (14.33 mmol).

[Example 5] Preparation of compound H-51

Preparation of Compound 5-1

33.5 g (128 mmol) of 4-phenyldibenzo [b, d] thiophene were dissolved in 650 mL of THF and then cooled to -78 ° C. 62 mL (153 mmol) of n-butyllithium (2.5 M in hexane) And then stirred for 1 hour. At the same temperature, 44 mL (192 mmol) of boron tri-isopropoxide [B (OiPr) ₃ ] was added and stirred overnight. After the stirring was completed, the reaction solution was quenched by the addition of 1 M HCl, extracted with distilled water and EA, and then the organic layer was concentrated. Recrystallization from EA and Hex afforded compound 5-1, 19 g (64 mmol, 50%).

Preparation of Compound 5-2

Compound 2-1 (8g, 35.54mmol), compound 5-1 (12.9g, 42.65mmol), Pd (PPh 3) 4 (1.2g, 1.06mmol), 2M K 2 CO 3 35mL, ethylene glycol dimethyl ester and 150mL 100 mL of ethanol was added and the mixture was stirred under reflux. After 3 hours, the reaction mixture was cooled to room temperature, methanol was added thereto, and the resulting solid was filtered under reduced pressure. The solid was separated into a column to give compound 5-2, 9g (56.4%).

Preparation of Compound H-51

Compound H-51 (1.8 g, 27%) was obtained in the same manner as Compound H-2 by using Compound 5-2 (9 g, 20 mmol) and Compound 1-2 (7 g, 0.018 mol).

[Example 6] Preparation of Compound H-55

Preparation of Compound 6-1

3L round bottom flask 1,4-dibromo-2-nitrobenzene (50g, 278mmol), [1,1'- biphenyl] -4-Daily acid (32g, 252mmol), Pd ( PPh 3) 4 (5.5 _{g, 7.56mmol), Na 2 CO} 3 (42.7g, 403mol), H 2 O (400mL), into the EtOH (400ml) and toluene (800mL) was stirred under reflux for 3 hours. After the reaction was completed, the reaction mixture was cooled and extracted with EA and H ₂ O. The EA layer was dried with MgSO ₄ . The EA layer is concentrated under reduced pressure and then columned with silica gel. The resulting solution was concentrated under reduced pressure to obtain 30.5 g (34%) of Compound 6-1.

Preparation of Compound 6-2

2L round bottom flask the compound 6-1 (30g, 84.7mmol), phenylboronic acid (13.42g 110.1mmol), Pd (PPh 3) 4 (2.89g, 2.5mmol), K 2 CO 3 (29.3g, 211.8mol) , H ₂ O (100 ml), EtOH (100 ml) and toluene (300 ml) were added, and the mixture was refluxed with stirring for 4 hours. When the reaction is completed, it is cooled and poured into a solid by pouring MeOH. The solid is columned with silica gel. The resulting solution was concentrated under reduced pressure to obtain 26.5 g (90%) of Compound 6-2.

Preparation of Compound 6-3

Compound 6-2 (26.5 g, 75.4 mmol) was used to synthesize Compound 6-3, 13 g (60%) in the same manner as Compound 1-2.

Preparation of compound H-55

Compound H-55 (6 g, 58%) was obtained in the same manner as Compound H-2 by using Compound 6-3 (4.5 g, 15.7 mmol) and Compound 2-2 (6.5 g, 17.4 mmol).

[Example 7] Preparation of Compound H-67

Compound H-67, 2.7 g (24%) was obtained by the same method as Compound H-2, using Compound 3-4 (5.6 g, 17.6 mmol) and Compound 2-2 (7.5 g, 20 mmol).

[Example 8] Preparation of compound H-68

Preparation of Compound 8-1

4-ylboronic acid (30 g, 131 mmol), 1-bromo-3-iodobenzene (44.65 g 158 mmol), Pd (PPh ₃ ) ₄ (4.5 g, 4 mmol), K ₂ CO ₃ (36 g, 263 mmol), toluene (300 mL), EtOH (75 mL) and H ₂ O (75 mL) were added and stirred under reflux. After 4 h, the mixture was extracted with DCM and H ₂ O and the DCM layer was dried over MgSO ₄ and filtered. The obtained solid was dissolved in CHCl _{3, and the product} was subjected to column chromatography with silica gel to obtain 31.38 g (69%) of Compound 8-1.

Preparation of Compound 8-2

Compound 8-1 (31 g, 91 mmol) was added to a 500 mL round-bottomed flask, 300 mL of THF was added, and the mixture was cooled to -78 ^° C. 2.5M n-butyllithium (44 mL, 110 mmol) was added and after 1 hour isopropyl borate (31.6 mL, 137 mmol) was added. After 17 hours, the mixture was extracted with ethyl acetate (EA) and H ₂ O and the EA layer was dried with MgSO ₄ . The EA layer was concentrated to give 22 g (79%) of compound 8-2.

Preparation of Compound 8-3

1L round bottom flask the compound 8-2 (22g, 72mmol), 1,3- dichloropyrimidine (13g, 87mmol), Pd ( PPh 3) 4 (2.5g, 2mmol), K 2 CO 3 (20g, 144mmol) and toluene (280mL), was stirred under reflux into the _{EtOH (70mL, H 2 O (} 70ml). filtered, then after 13 hours and extracted with DCM and H ₂ O and dried to give the DCM layer with MgSO _4. the solid obtained in CHCl ₃ The residue was subjected to column chromatography on silica gel to obtain 17.5 g (65%) of compound 8-3.

Preparation of compound H-68

The compound H-68 was synthesized in the same manner as the compound H-2, using Compound 3-4 (4.2 g, 13.2 mmol) and Compound 8-3 (3.5 g, 11 mmol). 1.1 g (18%) of Compound H-68 was obtained.

[Example 9] Preparation of Compound 69

Synthesis was conducted in the same manner as in the synthesis of the compound H-4 using Compound 6-3 (5 g, 15.6 mmol) and Compound 8-3 (7 g, 18.8 mmol) to give 4.5 g (43%) of the compound H-69.

[Example 10] Preparation of Compound H-70

Preparation of Compound 10-1

Compound 5-1, 9.4g (30.9mmol), 2,4- dichloro-pyrimidine 5.5g (37.1mmol), Pd (PPh 3) 4 1.1g (0.88mmol) and Na ₂ CO ₃ 8.2g (77.2mmol) Was added to 160 mL of toluene, 40 mL of ethanol and 40 mL of distilled water, and the mixture was stirred at 120 ° C for 5 hours. After the stirring was completed, the purified water was slowly added thereto to terminate the reaction. The reaction mixture was cooled to room temperature and extracted with distilled water and MC. The organic layer was concentrated and then separated into a column (MC / Hex) to obtain 8.9 g (78%) of compound 10-1.

Preparation of compound H-70

Compound H-2 was synthesized by using Compound 1-2, 4.1 g (17.0 mmol) of Compound 10-1 and 5.3 g (14.2 mmol) of Compound 10-1, H-70, 4.5 g (55%).

[Example 11] Preparation of compound H-71

Preparation of Compound 11-1

2,4-dibromo-nitrobenzene in the flask (18.7g, 66.57 mmol), biphenyl-4-boronic acid (14.5g, 73.23mmol), Pd ( PPh 3) 4 4g (3.33mmol) and 2M Na ₂ CO ₃ was dissolved in 330 mL of toluene and 130 mL of ethanol, and the mixture was refluxed at 120 DEG C for 5 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residue was dried with magnesium sulfate, and then dried. The organic layer was separated into a column and 12g (yield: 52%).

Preparation of Compound 11-2

Compound 11-1, 12g (33.87 mmol) and phenylboronic acid 4.5g (37.26 mmol) were synthesized in the same manner as Compound 4-1 to give 11g (98%) of Compound 11-2.

Preparation of Compound 11-3

Compound 11-2 (11 g, 31.30 mmol) was dissolved in 120 mL of triethyl phosphate and refluxed at 150 ° C for 6 hours. After the reaction was completed, the reaction mixture was distilled and triturated with MeOH to obtain 6.5 g (yield: 60%) of Compound 11-3.

Preparation of Compound H-71

The compound H-71 was synthesized in the same manner as the compound H-2 using 3.5 g (10.95 mmol) of the compound 11-3 and 3.4 g (13.14 mmol) of the compound 1-3, to give 1 g (yield: 16% Respectively.

[Example 12] Preparation of Compound H-72

Compound H-72 was synthesized in the same manner as Compound H-2, using Compound 6-3 (5 g, 15.7 mmol) and Compound 1-3 (5.1 g, 17.3 mmol)

[Example 13] Preparation of compound H-73

The compound H-73 was synthesized in the same manner as the compound H-2 by using Compound 1-2 (7.3 g, 30 mmol) and Compound 8-3 (13.5 g, 36 mmol) to obtain 4.5 g (25%) of Compound H-73.

[Example 14] Preparation of compound H-147

Preparation of Compound 14-1

Round bottom flask of 500mL 2- bromo -9H- carbazole (37g, 133mmol), 4- biphenyl boronic acid (31g, 159.6mmol), Pd ( PPh 3) 4 (3g, 2.66mmol), K 2 CO 3 (37 g, 266 mmol), EtOH (60 mL), purified water (60 mL) and toluene (250 mL), and the mixture was refluxed with stirring for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and subjected to column chromatography to obtain compounds 14-1 and 33g (78%).

Preparation of Compound H-147

Compound H-147 (1.1 g, 11%) was obtained in the same manner as Compound H-2 by using Compound 14-1 (5 g, 15.7 mmol) and Compound 8-3 (6.4 g, 17.3 mmol).

The physical properties data of the compounds prepared in Examples 1 to 14 and the compounds prepared in the same manner are shown in Table 1 below.

High temperature Thermal stability  Measure

The organic electroluminescent compound according to the present invention was exposed to heat at a high temperature higher than the deposition temperature (Ts) for the fabrication of the light emitting device and the deposition temperature for a long time, and the compound was subjected to purity analysis using HPLC.

The analytical instrument used for the purity measurement is the 1290 Infinity Binary Pump VL, the 1290 Infinity Autosampler, the 1290 Infinity Thermostatted Column Compartment and the 1290 Infinity Diode Array Detector. The column used is ZORBAX eclipse plus C18 4.6 X150 mm 3.5 MICRON.

2 mg of each sample was dissolved in 10 ml of tetrahydrofuran (THF), and 5 μl of the resulting solution was taken. The mobile phase was a mixed solution of tetrahydrofuran: distilled water = 55: 45 and measured at a flow rate of 1 ml / min .

As a result, it was confirmed that the initial purity was maintained at a high temperature without changing the purity.

Ts  : Deposition temperature

[Device Embodiment 1] Fabrication of OLED element using organic electroluminescent compound according to the present invention

An OLED device having a structure using the light emitting material of the present invention was fabricated. First, a transparent electrode ITO thin film (15 OMEGA / square) obtained from a glass for OLED (manufactured by Samsung Corning) was subjected to ultrasonic cleaning using trichlorethylene, acetone, ethanol and distilled water sequentially and then stored in isopropanol Respectively. Next, an ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus, and N ¹ , N ^{1 '} - ([1,1'-biphenyl] -4,4'-diyl) bis ¹ - (naphthalene- ¹ -yl) -N ⁴ , N ⁴ -diphenylbenzene-1,4-diamine) was added and the chamber was evacuated until the degree of vacuum reached 10 ^-6 torr. And evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'- diaminobiphenyl was added to another cell in the vacuum vapor- Was evaporated to deposit a hole transport layer having a thickness of 20 nm on the hole injection layer. After the hole injecting layer and the hole transporting layer were formed, a light emitting layer was deposited thereon as follows. Compound H-2 as a host was placed in one cell in a vacuum deposition apparatus and Compound D-1 was added as a dopant in another cell. Then, the two materials were evaporated at different rates to prepare a dopant with a dopant content of 15% The light emitting layer having a thickness of 30 nm was deposited on the hole transporting layer. Then, on one side of the luminescent layer as an electron transporting layer was added a solution of 2- (4- (9,10-di (naphthalen-2-yl) anthracen- And lithium quinolate was added to another cell. Then, the two materials were evaporated at the same rate and doped in an amount of 50% by weight, respectively, to deposit an electron transport layer of 30 nm. Then, lithium quinolate was deposited to a thickness of 2 nm as an electron injecting layer, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum vapor deposition equipment to fabricate an OLED device. Each compound was purified by vacuum sublimation under 10 ^-6 torr.

As a result, a current of 2.10 mA / cm ² was passed at 2.8 V, and green emission of 1020 cd / m ² was confirmed. Also, it took more than 190 hours for light emission to drop to 80% at a luminance of 15000 nit.

[Device Embodiment 2] An OLED device using an organic electroluminescent compound according to the present invention

Fabrication An OLED device was fabricated in the same manner as in Example 1 except that Compound H-72 was used as a host and Compound D-1 was used as a dopant.

As a result, a current of 7.83 mA / cm < ² > flowed at 3.1 V, and green emission of 3200 cd / m < ² > Also, it took more than 170 hours for the emission to fall to 80% at a luminance of 15000 nit.

[Device Embodiment 3] An OLED device using an organic electroluminescent compound according to the present invention

Fabrication An OLED device was fabricated in the same manner as in Example 1 except that Compound H-5 was used as a host and Compound D-1 was used as a dopant.

As a result, a current of 5.93 mA / cm < ² > flows at 3.1 V and green emission of 2350 cd / m < ² > Also, it took more than 120 hours for the emission to fall to 80% at a luminance of 15000 nit.

[Device Embodiment 4] An OLED device using an organic electroluminescent compound according to the present invention

Fabrication An OLED device was fabricated in the same manner as in Example 1 except that Compound H-71 was used as a host and Compound D-1 was used as a dopant.

As a result, a current of 2.94 mA / cm ² flowed at 2.9 V and green luminescence of 1500 cd / m ² was confirmed. Also, it took more than 160 hours for the emission to fall to 80% at a luminance of 15000 nit.

[Element Embodiment 5] An OLED element using an organic electroluminescent compound according to the present invention

Fabrication An OLED device was fabricated in the same manner as in Example 1 except that Compound H-4 was used as a host and Compound D-1 was used as a dopant.

As a result, a current of 2.84 mA / cm < ² > flowed at 2.6 V, and green emission of 1340 cd / m < ² > Also, it took more than 230 hours for the emission to fall to 80% at a luminance of 15000 nit.

[Device Embodiment 6] An OLED device using an organic electroluminescent compound according to the present invention

Fabrication An OLED device was fabricated in the same manner as in Example 1 except that Compound H-9 was used as a host and Compound D-1 was used as a dopant.

As a result, a current of 4.73 mA / cm ² was passed at 3.0 V, and green emission of 2130 cd / m ² was confirmed. Also, it took more than 180 hours for the light emission to drop to 80% at a luminance of 15000 nit.

[Device Example 7] An OLED device using an organic electroluminescent compound according to the present invention

Fabrication An OLED device was fabricated in the same manner as in Example 1 except that Compound H-68 was used as a host and Compound D-1 was used as a dopant.

As a result, a current of 6.13 mA / cm < ² > flows at 3.2 V, and green emission of 2610 cd / m < ² > Also, it took more than 185 hours for the emission to fall to 80% at a luminance of 15000 nit.

[Device Embodiment 8] An OLED device using an organic electroluminescent compound according to the present invention

Fabrication An OLED device was fabricated in the same manner as in Example 1 except that Compound H-26 was used as a host and Compound D-1 was used as a dopant.

As a result, a current of 8.09 mA / cm ² flowed at 2.9 V, and green emission of 3320 cd / m ² was confirmed. Also, it took more than 230 hours for the emission to fall to 80% at a luminance of 15000 nit.

[Device Embodiment 9] An OLED device using an organic electroluminescent compound according to the present invention

Fabrication An OLED device was fabricated in the same manner as in Example 1 except that Compound H-67 was used as a host and Compound D-1 was used as a dopant.

As a result, a current of 5.27 mA / cm ² flowed at 2.7 V, and green emission of 2040 cd / m ² was confirmed. Also, it took more than 250 hours for the light emission to drop to 80% at a luminance of 15000 nit.

[Device Embodiment 10] An OLED device using an organic electroluminescent compound according to the present invention

Fabrication An OLED device was fabricated in the same manner as in Example 1 except that Compound H-55 was used as a host and Compound D-1 was used as a dopant.

As a result, a current of 4.57 mA / cm ² flowed at 2.9 V, and green emission of 1820 cd / m ² was confirmed. Also, it took more than 250 hours for the light emission to drop to 80% at a luminance of 15000 nit.

[Element Embodiment 11] An OLED element using an organic electroluminescent compound according to the present invention

Fabrication An OLED device was fabricated in the same manner as in Example 1 except that Compound H-51 was used as a host and Compound D-1 was used as a dopant.

As a result, a current of 3.51 mA / cm ² flowed at 2.8 V, and green emission of 1640 cd / m ² was confirmed. Also, it took more than 200 hours for the light emission to drop to 80% at a luminance of 15000 nit.

[Comparative Example 1] Luminescence characteristics of OLED device using conventional light emitting material

Except that iridium tris (2-phenylpyridine) [Ir (ppy) ₃ ] was used as a dopant and C-1 was used instead of the compound of the present invention as a host material in one cell in a vacuum vapor deposition equipment. To fabricate an OLED device.

As a result, a current of 14.97 mA / cm < ² > flowed at 4.3 V, and green emission of 2420 cd / m < ² > Also, it took 23 hours for the emission to fall to 80% at a luminance of 15000 nit.

[Comparative Example 2] Luminescence characteristics of OLED device using conventional light emitting material

An OLED device was fabricated in the same manner as in Example 1 except that C-2 was used instead of the compound of the present invention as a host material and Ir (ppy) ₃ was used as a dopant in one cell in a vacuum deposition equipment.

As a result, a current of 4.85 mA / cm < ² > was passed at 4.2 V, and green emission of 1820 cd / m < ² > Also, it took 54 hours for the emission to fall to 80% at a luminance of 15000 nit.

[Comparative Example 3] Luminescent characteristics of OLED device using conventional light emitting material

An OLED device was fabricated in the same manner as in Example 1 except that C-3 was used instead of the compound of the present invention as a host material and Ir (ppy) ₃ was used as a dopant in one cell in a vacuum vapor deposition equipment.

As a result, a current of 8.15 mA / cm < ² > flows at 4.8 V, and green emission of 2810 cd / m < ² > Also, it took 35 hours for the emission to drop to 80% at a luminance of 15000 nit.

[Comparative Example 4] Luminescent characteristics of OLED devices using conventional light emitting materials

An OLED device was fabricated in the same manner as in Example 1 except that C-4 was used instead of the compound of the present invention as a host material and Ir (ppy) ₃ was used as a dopant in one cell in a vacuum deposition equipment.

As a result, it took 75 hours for the emission to fall to 80% at a luminance of 15000 nit.

The organic electroluminescent compounds developed in the present invention are excellent in thermal stability and have better luminescent characteristics and better lifetime characteristics than conventional materials. In addition, the organic electroluminescent device using the organic electroluminescent compound according to the present invention as a host material for green emission has a low driving voltage and improved current efficiency and operating life.

Claims (6)

An organic electroluminescent compound represented by the following Formula 1:
[Chemical Formula 1]

In Formula 1,
L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (3-30 membered heteroarylene, or substituted or unsubstituted (C6-C30) arylene;
X ₁ And X < ₂ & Each independently CH or N;
Y is -O-, -S-, -CR ₁₁ R ₁₂ -or -NR _13- ;
Ar ₁ is substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;
Ar ₂ is hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;
R ₁ to R ₃ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, Substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (5-7 membered) heterocycloalkyl, _{NR 14 R 15, -SiR 16 R} 17 R 18, -SR 19, -OR 20, cyano, nitro or hydroxyl, or a monocyclic or polycyclic with an adjacent substituent via (C5-C30) cycloaliphatic or aromatic ring And the carbon atom of the alicyclic or aromatic ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;
R ₁₁ to R ₂₀ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted (C5-C30) cycloaliphatic or heteroaryl, together with the adjacent substituents, are optionally substituted with one or more substituents independently selected from the group consisting of (C5-C30) cycloalkyl, substituted or unsubstituted And the carbon atom of the alicyclic or aromatic ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;
a and c are each independently an integer of 1 to 4, and when a or c is an integer of 2 or more, each R ₁ or each R ₃ may be the same or different;
b is an integer of 1 to 3, and when b is an integer of 2 or more, each R ₂ may be the same or different
The heteroarylene, heterocycloalkyl and heteroaryl comprise at least one heteroatom selected from B, N, O, S, P (= O), Si and P. 2. The method of claim 1, wherein L _1, L _2, Ar _1, Ar _2, R ₁ to R _3, R ₁₁ to a substituted alkyl in R _20, optionally substituted aryl (alkylene), substituted heteroaryl (alkylene), substituted cycloalkyl (C6-C30) aryl, (C6-C30) aryl (C1-C30) alkyl optionally substituted by deuterium, halogen, halogen, (C3-C30) cycloalkyl, (5-7 membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, (C1-C30) alkylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, N (C6-C30) arylamino, di (C6-C30) arylcarbonyl, di (C1-C30) alkylamino, di (C6-C30) aryl (C1-C30) alkyl, (C1-C30) Carboxyl, nitro, and hydro The organic electroluminescent compounds characterized in that at least one selected from the group consisting of. The compound of claim 1, wherein L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (3-15 membered) heteroarylene, or substituted or unsubstituted (C 6 -C 15) arylene;
The X ₁ And X < ₂ & Each independently CH or N;
Y is -O-, -S- or -CR ₁₁ R _12- ;
Wherein Ar < ₁ > is substituted or unsubstituted (C6-C15) aryl, or substituted or unsubstituted (3-15 membered) heteroaryl;
Wherein Ar < ₂ > is hydrogen, substituted or unsubstituted (C6-C15) aryl, or substituted or unsubstituted (3-15 membered) heteroaryl;
Wherein R ₁ to R ₃ are each independently hydrogen, substituted or unsubstituted (C6-C15) aryl, or substituted or unsubstituted (3-30 membered heteroaryl), or together with adjacent substituents, C5-C30) alicyclic or aromatic ring, and the carbon atom of the alicyclic or aromatic ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;
Wherein each of a to c is independently an integer of 1 or 2. 2. The organic electroluminescent compound according to claim 1, The compound of claim 1, wherein L ₁ and L ₂ are each independently a single bond, unsubstituted (3-10 membered heteroarylene, or substituted or unsubstituted (C6-C10) arylene;
The X ₁ And X < ₂ & Each independently CH or N;
Y is -O- or -S-;
Wherein Ar ₁ is substituted or unsubstituted (C 6 -C 10) aryl, or substituted (3-15 member) heteroaryl;
Said Ar ₂ is hydrogen, substituted or unsubstituted (C6-C15) aryl, or substituted (3-15 membered) heteroaryl;
Wherein each of R ₁ to R ₃ is independently hydrogen or substituted or unsubstituted (C 6 -C 10) aryl or may form a monocyclic or polycyclic (C 5 -C 30) alicyclic or aromatic ring together with the adjacent substituents, The carbon atom of the alicyclic or aromatic ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;
And a to c are an integer of 1. The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 1 is selected from the following compounds.

An organic electroluminescent device comprising the compound according to claim 1.