KR20110077930A - Organic electroluminescent compounds and organic electroluminescent device comprising same - Google Patents

Abstract

PURPOSE: An organic luminescent compound is provided to ensure excellent hole injection and/or transport ability, and electron transport ability and/or light-emitting capability and to obtain an organic electroluminescence device with good luminous efficiency, brightness, driving voltage, and life span. CONSTITUTION: An organic electroluminescence device includes a positive electrode, a negative electrode, and a monolayered or multilayered organic layer interposed between the positive and negative electrodes. At least one of the organic layers comprises the compound of chemical formula 1. In chemical formula 1, X is N, S or O; and A is substituted or unsubstituted monocyclic or fused polycyclic heterocycle having 6-40 nucleus atoms, when at least one X-containing ring is an aromatic ring having 6-8 nucleus atoms.

Description

Organic light emitting compound and organic electroluminescent device including the same {ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING SAME}

The present invention includes an organic light emitting compound having excellent electron transporting ability, hole injection and / or transporting ability, and / or light emitting ability, and an organic light emitting compound having improved characteristics such as luminous efficiency, luminance, thermal stability, driving voltage, and lifetime by including the same in one or more organic layers. It relates to an electroluminescent element.

An organic electronic device is an electronic device using an organic semiconductor material, and requires an exchange of holes and / or electrons between an electrode and an organic semiconductor material.

The organic electronic device can be divided into two types according to the operating principle. First, an exciton is formed in the organic layer by photons introduced from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form. The second type is an electronic device in which holes and / or electrons are injected into the organic semiconductor material layer that interfaces with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.

Examples of organic electronic devices include organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices'), organic solar cells, organic photosensitive (OPC) drums, organic transistors, etc., all of which drive the devices. For this purpose, an electron / hole injection material, an electron / hole extraction material, an electron / hole transport material or a light emitting material is required. Hereinafter, the organic EL device will be described in detail. However, in the organic EL device, an electron / hole injection material, an electron / hole extraction material, an electron / hole transport material, or a light emitting material all work on a similar principle.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic EL device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic layer therebetween. The organic layer is often formed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic EL device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.

In the structure of the organic EL device, when a voltage is applied between two electrodes, holes are injected into the organic layer at the anode and electrons are injected into the organic layer, and excitons are formed when the injected holes and electrons meet. When the excitons fall to the ground, they shine.

The material used as the organic layer in the organic EL device may be classified into a light emitting material, a charge transport material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like depending on the function.

The light emitting material may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color. In addition, in order to increase luminous efficiency through increase in color purity and energy transfer, a host / dopant system may be used as the light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

Especially in the case of phosphorescence can be expected theoretically 100% luminous effect than fluorescence. Therefore, the luminous efficiency may be higher than the luminous efficiency of 25% in fluorescence.

However, phosphorescent materials are currently slower to develop than fluorescent lamps and are inferior in life for prototype applications.

In order to fully exhibit the excellent characteristics of the organic EL device, the material forming the organic layer in the device, that is, the hole injection material, the hole transport material, the light emitting material, the electron transport material, the electron injection material, etc., is supported by a stable and efficient material. It should be noted, however, that the development of a stable and efficient organic layer material for an organic EL device has not been sufficiently achieved. Accordingly, development of a new material is continuously required.

Accordingly, an object of the present invention is to provide an organic light emitting compound having excellent electron transporting ability, hole injection and / or transporting ability, and / or light emitting ability (fluorescence or phosphorescence) and the light emitting efficiency, luminance, thermal stability, It is to provide an organic EL device having improved characteristics such as driving voltage and lifetime.

The present invention in order to achieve the above object; cathode; And at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers comprises a compound represented by Formula 1 below:

<Formula 1>

Where

X is N, S or O;

A means substituted or unsubstituted, monocyclic or fused polycyclic heterocycle, having 6 to 40 nuclear atoms, provided that at least the X-containing ring is nuclear 6 to 8 aromatic rings;

R ₁ to R ₁₀ are each independently hydrogen, deuterium, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C2-C40 alkynyl, substituted or unsubstituted C5-C40 aryl, substituted or unsubstituted heteroaryl having 5 to 40 nuclear atoms, substituted or unsubstituted C5-C40 aryloxy, substituted or unsubstituted C1-C40 alkyloxy, substituted or unsubstituted C5-C40 Arylamino, substituted or unsubstituted C5-C40 diarylamino, (substituted or unsubstituted C6-C40 aryl) C1-C40 alkyl, substituted or unsubstituted C3-C40 cycloalkyl, or substituted or unsubstituted nuclear atom 3 to 40 heterocycloalkyl, R ₅ and R ₆ may be linked to form a condensed ring.

The present invention also provides a compound represented by Formula 1a or 1b:

Where

A, X, R ₁ to R ₁₀ are as defined above;

R ₁₁ to R ₂₁ are as defined in R ₁ to R ₁₀ ;

L is a direct bond, substituted or unsubstituted C6-C40 aryl or substituted or unsubstituted heteroaryl having 6 to 40 nuclear atoms.

When the organic light emitting compound according to the present invention is adopted as a phosphorescent or fluorescent host material of an organic EL device, energy transfer from the host to the dopant can be smoothly performed as compared with the conventional light emitting material. Therefore, the organic EL device according to the present invention can exhibit excellent characteristics in terms of luminous efficiency, brightness, power efficiency, driving voltage and lifetime, and thus can be effectively applied to a full color display panel.

The present invention provides a phenazine having excellent electron donating ability through a linker (L) or a hole-providing compound moiety such as triphenylene, which does not sufficiently exhibit its characteristics as a phosphorescent host. Incorporating an organic light emitting compound of formula (I) that connects to a series of compound moieties to achieve a sufficiently high triplet energy level, thereby improving phosphorescence properties and simultaneously providing electron and / or hole transport capabilities, Provided is an organic EL device having improved luminous efficiency, driving voltage, lifetime, and the like.

In the organic EL device of the present invention, the compound of formula (1) is a compound wherein X is N, S or O; A monocyclic or fused polycyclic heterocycle having 6 to 40 nuclear atoms, wherein A is substituted or unsubstituted, wherein at least the X-containing ring is 6 nuclear atoms To 8 is an aromatic ring.

R ₁ to R ₁₀ are each independently hydrogen, deuterium, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C2-C40 alkynyl, substituted or unsubstituted C5-C40 aryl, substituted or unsubstituted heteroaryl having 5 to 40 nuclear atoms, substituted or unsubstituted C5-C40 aryloxy, substituted or unsubstituted C1-C40 alkyloxy, substituted or unsubstituted C5-C40 Arylamino, substituted or unsubstituted C5-C40 diarylamino, (substituted or unsubstituted C6-C40 aryl) C1-C40 alkyl, substituted or unsubstituted C3-C40 cycloalkyl, or substituted or unsubstituted nucleus 3 to 40 heterocycloalkyl, R ₅ and R ₆ may be linked to form a condensed ring.

Alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkyloxy, arylamino, diarylamino, arylalkyl, cycloalkyl and heterocycloalkyl of R ₁ to R ₁₀ are each independently deuterium, halogen, amino , Nitrile, nitro, C1-C40 alkyl, C2-C40 alkenyl, C1-C40 alkoxy, C3-C40 cycloalkyl, heterocycloalkyl of 3 to 40 nuclear atoms, C6-C40 aryl and 5 to 40 nuclear atoms It may be substituted with one or more substituents selected from the group consisting of heteroaryl.

Representative compounds of Formula 1 of the present invention may be compounds of Formula 1a or 1b:

<Formula 1a>

<Formula 1b>

Where

A, X, R ₁ to R ₁₀ are as defined above;

R ₁₁ to R ₂₁ are as defined in R ₁ to R ₁₀ ;

L is a direct bond, substituted or unsubstituted C6-C40 aryl or substituted or unsubstituted heteroaryl having 6 to 40 nuclear atoms, for example phenyl, biphenyl, terphenyl, naph Naphthyl, anthracenyl, phenanthryl, pyrenyl, fluorenyl, carbazolyl, N-carbazolephenyl, quinolinyl, iso Quinolinyl, and the like.

The aryl and heteroaryl of the linker L are each independently deuterium, C1-C40 alkyl, C3-C40 cycloalkyl, C2-C40 alkenyl, C1-C40 alkoxy, C1-C40 alkylamino, C6-C40 aryl and the number of nuclear atoms It may be substituted with one or more substituents selected from the group consisting of 5 to 40 heteroaryl, such substituents form spiro bonds with adjacent groups or condensation of aliphatic, aromatic, heteroaliphatic or heteroaromatics of 6 to 40 nuclear atoms. May form a ring.

In addition, the substituents of the linker L, alkyl, cycloalkyl, alkenyl, alkoxy, alkylamino, aryl and heteroaryl are each independently deuterium, halogen, amino, nitrile, nitro, C1-C40 alkyl, C2-C40 alkenyl , C1-C40 alkoxy, C3-C40 cycloalkyl, heterocycloalkyl having 3 to 40 nuclear atoms, C6-C40 aryl and heteroaryl having 5 to 40 nuclear atoms may be further substituted with one or more substituents. have.

As a non-limiting example, the linker L is preferably C6-C40 aryl or heteroaryl having 6 to 40 nuclear atoms selected from the group consisting of the following Chemical Formula 2.

Where

k, m and n are each independently integers ranging from 1 to 3;

The plurality of Q ¹ are the same or different from each other, the plurality of Q ² are the same or different from each other, and the plurality of Q ³ are the same or different from each other;

Q ¹ , Q ² and Q ³ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1-C40 alkyl; Substituted or unsubstituted C3-C40 cycloalkyl; Substituted or unsubstituted C2-C40 alkenyl; Substituted or unsubstituted C1-C40 alkoxy; Substituted or unsubstituted C1-C40 alkylamino; Substituted or unsubstituted C6-C40 aryl; Or a substituted or unsubstituted heteroaryl having 5 to 40 nuclear atoms, and these substituents may form a condensed ring of an aliphatic, aromatic, heteroaliphatic or heteroaromatic having adjacent groups with 6 to 40 nuclear atoms.

The alkyl, cycloalkyl, alkenyl, alkoxy, alkylamino, aryl and heteroaryl are each independently selected from small to medium, halogen, amino, nitrile, nitro, C1-C40 alkyl, C2-C40 alkenyl, C1-C40 alkoxy, C3 It may also be substituted with one or more substituents selected from the group consisting of -C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C40 aryl and heteroaryl groups having 5 to 40 nuclear atoms.

The following formulas are representative examples of the compound of formula 1 of the present invention, but the compounds of the present invention are not limited to those illustrated below.

As used herein, “unsubstituted heterocycle” means an aromatic or non-aromatic ring having 6 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, Substituted with a heteroatom such as O or S. Non-limiting examples of heterocycles include 3-1H-benzimidazol-2-one, 2-tetrahydrofuranyl, 2-tetrahydrothiophenyl, 2-morpholinyl, 3-morpholinyl, 1-pyrroli Dinyl, 1-piperazinyl, 2-piperazinyl, 4-thiazolidinyl, benzoxanyl, benzopyrrolidinyl, benzopiperidinyl, benzothianyl, etc. This includes. Furthermore, the heterocycles used herein are to be understood to include those condensed with one or more aromatic or non-aromatic rings. At least one hydrogen atom of the heterocycle is deuterium; C1-C40 alkyl; C3-C40 cycloalkyl; C2-C40 alkenyl; C1-C40 alkoxy; C1-C40 alkylamino; C6-C40 aryl; Or heteroaryl having 5 to 40 nuclear atoms, and the alkyl, cycloalkyl, alkenyl, alkoxy, alkylamino, aryl and heteroaryl are each independently deuterium, halogen, amino, nitrile, nitro, C1- One or more substituents selected from the group consisting of C40 alkyl, C2-C40 alkenyl, C1-C40 alkoxy, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C40 aryl and heteroaryl groups having 5 to 40 nuclear atoms It may be substituted with.

“Unsubstituted heterocycloalkyl” means a non-aromatic moiety having 3 to 40 nuclear atoms, in which one or more carbons in the ring, preferably 1 to 3 carbons, are replaced with a hetero atom such as N, O or S . Non-limiting examples thereof include morpholine, piperazine and the like.

“Unsubstituted heteroaryl” means a monoheterocyclic or polyheterocyclic aromatic moiety having 5 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O or S And substituted with a heteroatom such as It is understood that two or more rings may be attached in a simple or fused form to each other and further include a condensed form with an aryl group. Examples of heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl It is understood to include a ring and to include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.

Compounds of formula 1 of the present invention can be synthesized according to general synthetic methods (Macromoluecules, 38: 1131-1140 (2005); Organic Letters, 7: 4843-4846 (2005); J. Med. Chem, 44: 594 601 (2001); Chem Mater, 16: 5387-5393 (2004) et al.). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.

An organic EL device according to the present invention comprises: an anode; Cathode; And at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer includes a compound represented by Chemical Formula 1.

The compound of Formula 1 may be included alone or in plurality.

The organic layer including the compound of Formula 1 of the present invention may be any one or more of a hole injection layer, a hole transport layer, an electron transport layer and a light emitting layer. In the present invention, the light emitting layer may include a phosphorescent dopant material or a fluorescent dopant material. Preferably, the compound of formula 1 of the present invention may be included in the organic EL device as a blue, green, and / or red phosphorescent host, a fluorescent host, a hole transport material, a hole injection material and / or an electron transport material. More preferably, the compound of formula 1 of the present invention may be included in the organic EL device as a phosphorescent host.

Since the compound of the present invention has a high glass transition temperature, when the compound is used as the organic layer of the organic EL device, the crystallization is minimized in the organic EL device, so that the driving voltage of the device can be lowered, and the luminous efficiency, luminance, and thermal stability , And lifespan characteristics can be improved.

As a non-limiting example of the organic EL device structure according to the present invention, a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode may be sequentially stacked, wherein the light emitting layer, hole injection layer, At least one of the hole transport layer and the electron transport layer may include a compound represented by Chemical Formula 1. An electron injection layer may be positioned on the electron transport layer.

In addition, as described above, the organic EL device according to the present invention may not only have a structure in which an anode, at least one organic layer, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at the interface between the electrode and the organic layer.

In the organic EL device of the present invention, the organic layer including the compound of Formula 1 may be formed by vacuum deposition or solution coating. Examples of the solution application include spin coating, dip coating, doctor blading, inkjet printing or thermal transfer method, but is not limited thereto.

The organic EL device of the present invention forms an organic layer and an electrode using materials and methods known in the art, except that at least one of the organic layers is formed to include the compound represented by the formula (1) of the present invention. can do.

For example, a silicon wafer, quartz, glass plate, metal plate, plastic film or sheet may be used as the substrate.

The anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.

Cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer are not particularly limited, and conventional materials known in the art may be used.

Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the present invention and the present invention is not limited by the following examples.

< Synthetic example  1> Compound In Synthesis of -4

<Step 1> Synthesis of Compound 3

Compound 1 (10 g, 1 eq, 0.034 mol) and compound 2 (4.14 g, 1.1 eq, 0.038 mol) were added to a 1 L flask, 500 ml of 1-Butanol was added, and 1 ml of concentrated sulfuric acid was added thereto, followed by stirring under reflux for 12 hours. .

After completion of the reaction, the mixture was washed and extracted with 200 ml of distilled water and 300 ml of methylene chloride (MC). After removing the solvent, the resulting solid was purified by column chromatography to give compound 3 (10.2 g, 82% yield).

GC-Mass (Theoretical value: 359.22 g / mol, Measured value: 359 g / mol)

Step 2 Synthesis of Compound 4

500 ml of Compound 3 (10 g, 1eq, 0.027 mol) synthesized in the above <Step 1> was added to a flask, and 250 ml of THF was added thereto, and the reactor temperature was cooled to -78 ° C. 1.6M n-BuLi (21.3 mL, 1.2eq, 0.033mol) was slowly added thereto and stirred for approximately 1 hour.

After 1 hour of reaction, Triisopropylborate (7.6 mL, 1.2eq, 0.033mol) was added, and the temperature of the reactor was raised to room temperature, followed by stirring for about 12 hours.

After completion of the reaction, 100 ml of 1N HCl was added to the reaction solution, stirred for 30 minutes, and washed with 300 ml of ethyl acetate (EA) and 200 ml of distilled water. After removing the solvent, the resulting solid was stirred with 200 ml of n-Hexane. The resulting solid was filtered to give compound 4 (7.7 g, yield 88%).

GC-Mass (Theoretical value: 324.14g / mol, Measured value: 324g / mol)

<Step 3> Compound In Synthesis of -4

Compound 5 (6.9g, 1eq, 0.017mol) and compound 4 (7g, 1.2eq, 0.021mol) synthesized in <Step 2> were placed in a flask and Pd (PPh3) 4 (0.39g, 0.02eq, 0.0003mol) Was added. 250 ml of Toluene and 2M K ₂ CO ₃ were added and then stirred at reflux for 5 hours.

After completion of the reaction, the resultant was washed and extracted with 500 ml of MC and 200 ml of distilled water, and then the solvent was removed, and the resulting solid was purified by column chromatography to obtain the title compound In-4 (7.4 g, yield 75%).

GC-Mass (Theoretical value: 582.69 g / mol, Measured value: 582 g / mol)

< Synthetic example  2> compound In Synthesis of -7

<Step 1> Synthesis of Compound 2-3

Compound 2-1 (10 g, 1 eq, 0.034 mol) and compound 2-2 (4.14 g, 1.1 eq, 0.038 mol) were added to a 1 L flask and 500 ml of acetic acid was added, followed by stirring under reflux for 12 hours.

After the reaction was completed, 1L of distilled water was added, and the produced solid was filtered and dissolved in MC, followed by washing with 200 ml of distilled water. The solvent was removed and the resulting solid was purified by column chromatography to give compound 2-3 (10 g, 80% yield).

GC-Mass (Theoretical value: 361.23, Measured value: 361)

Step 2 Synthesis of Compound 2-4

Compound 2-3 (10 g, 1 eq, 0.027 mol) synthesized in the above <Step 1> was placed in a 500 mL flask, and 250 mL of THF was added thereto. After cooling the reactor temperature to -78 ° C, 1.6M n-BuLi (21.3 mL, 1.2eq, 0.033mol) was slowly added thereto and stirred for approximately 1 hour.

After 1 hour of reaction, Triisopropylborate (7.6 mL, 1.2eq, 0.033mol) was added to the reactor, and the temperature of the reactor was raised to room temperature, followed by stirring for about 12 hours.

After the reaction was completed, 100 ml of 1N HCl was added to the reaction solution, which was stirred for 30 minutes. After washing and extraction with 300 ml of EA and 200 ml of distilled water, the solvent was removed, and the solid obtained by stirring was mixed with 200 ml of n-Hexane. The resulting solid was filtered to give compound 2-4 (7.6 g, yield 87%).

GC-Mass (Theoretical value: 326.16 g / mol, Measured value: 326 g / mol)

<Step 3> Compound In Synthesis of -7

Compound 2-5 (6.9g, 1eq, 0.017mol) and compound 2-4 (7g, 1.2eq, 0.021mol) synthesized in step <2> were placed in a flask, and Pd (PPh3) 4 (0.39g, 0.02eq , 0.0003 mol) was added. 250 ml Toluene and 2M K ₂ CO ₃ were added and then stirred at reflux for 5 hours.

After completion of the reaction, the resultant was washed and extracted with 500 ml of MC and 200 ml of distilled water, and then the solvent was removed. The resulting solid was purified by column chromatography to obtain the title compound In-4 (7.9 g, yield 80.1%).

GC-Mass (Theoretical value: 584.71 g / mol, Measured value: 584 g / mol)

< Synthetic example  3> Compound In Synthesis of -12

The same method as in Synthesis Example 1 was conducted, but using 6.8 g of Compound 12-1 and 0.4 g of Pd (PPh 3) 4 in <Step 3>, the title compound In-12 (7.8 g, yield 75%) was obtained.

GC-Mass (Theoretical value: 582.69 g / mol, Measured value: 582 g / mol)

< Synthetic example  4> Compound In Synthesis of -14

Perform the same method as in Synthesis Example 2, except that in Step 3, Compound 14-2 (7.2 g, 1 eq, 0.018 mol), Compound 2-4 (7.5 g, 1.2 eq, 0.022 mol), and Pd (PPh 3) 4 (0.41 g, 0.02eq, 0.0003 mol) was used to give the title compound In-14 (8.4 g, yield 82.6%).

GC-Mass (Theoretical value: 584.71 g / mol, Measured value: 584 g / mol)

< Synthetic example  5> Compound In Synthesis of -25

Perform the same method as in Synthesis Example 1, except that in Step 3, Compound 25-2 (6g, 0.0112mol, 1eq), Compound 4 (4.35g, 0.0134mol, 1.2eq), and Pd (PPh3) 4 (0.38g , 0.0003 mol, 0.03eq) gave the title compound In-25 (9.7 g, yield 85.4%).

GC-Mass (Theoretical value: 734.88 g / mol, Measured value: 734 g / mol)

< Synthetic example  6> Compound In Synthesis of -28

Perform the same method as in Synthesis Example 1, except that in Step 3, Compound 28-2 (4.5 g, 0.0109 mol, 1 eq), Compound 4 (4.23 g, 0.013 mol, 1.2 eq), and Pd (PPh 3) 4 (0.35) g, 0.00029 mol, 0.03 eq) gave the title compound In-28 (8.2 g, yield 81.3%).

GC-Mass (Theoretical value: 610.74 g / mol, Measured value: 610 g / mol)

< Synthetic example  7> Compound In Synthesis of -31

Perform the same method as in Synthesis Example 2, except that in Step 3, Compound 28-2 (4.5 g, 0.0109 mol, 1eq), Compound 2-4 (4.21 g, 0.013 mol, 1.2eq), and Pd (PPh3) 4 (0.35 g, 0.00029 mol, 0.03 eq) was used to give the title compound In-31 (7.9 g, yield 80.3%).

GC-Mass (Theoretical value: 610.74 g / mol, Measured value: 610 g / mol)

< Synthetic example  8> Compound In Synthesis of -36

Perform the same method as in Synthesis Example 1, except that in Step 3, Compound 36-2 (4.8 g, 0.0125 mol, 1 eq), Compound 4 (4.86 g, 0.015 mol, 1.2 eq), and Pd (PPh 3) 4 (0.43) g, 0.00375 mol, 0.03 eq) gave the title compound In-36 (8.4 g, yield 87.1%).

GC-Mass (Theoretical value: 583.68 g / mol, Measured value: 583 g / mol)

< Synthetic example  9> Compound In Synthesis of -38

Perform the same method as in Synthesis Example 2, except that in Step 3, Compound 38-2 (4.2 g, 0.0109 mol, 1 eq), Compound 2-4 (4.56 g, 0.015 mol, 1.2 eq), and Pd (PPh 3) 4 (0.41 g, 0.0035 mol, 0.03 eq) was used to give the title compound In-38 (7.9 g, yield 80.2%).

GC-Mass (Theoretical value: 612.76 g / mol, Measured value: 612 g / mol)

[ Example  1] organic EL  Manufacture of device

A glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol and the like was dried and then transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum depositor.

The hole injection layer was formed by thermal vacuum deposition of DS-205 (Doosan Co., Ltd.) at a thickness of 800 kPa on the prepared ITO (anode), and a-NPB (N, N-di (naphthalene-), a hole transport material, was formed on the hole injection layer. 1-yl) -N, N-diphenylbenzidine) was vacuum deposited to 150 mm thick.

The compound Inv-4 and Ir (ppy) 3 prepared in Synthesis Example 1 were vacuum deposited to a thickness of 300 Å to form a light emitting layer, and a BCP, a hole blocking layer material, was formed to a thickness of 200 위에 on the light emitting layer, followed by an electron transporting material. Phosphorus Alq3 was vacuum deposited to a thickness of 250 mm 3. Subsequently, LiF, which is an electron injection material, was deposited to a thickness of 10 GPa, and aluminum (cathode) was vacuum deposited to a thickness of 2000 GPa to prepare an organic EL device having a structure as shown in Table 1 below.

[ Example  2 ~ 8] organic EL  Manufacture of device

An organic EL device was manufactured in the same manner as in Example 1, except that the compound prepared in Synthesis Example 2-9 was used instead of the compound In-4 prepared in Synthesis Example 1 to form an emission layer.

[ Comparative example  1] organic EL  Manufacture of device

An organic EL device was manufactured in the same manner as in Example 1, except that CBP, which is a host mainly used as a green phosphorescent host, was used instead of the compound prepared in Synthesis Example when forming an emission layer.

Hole injection layer
(HIL) Hole transport layer
(HTL) Light emitting layer
(EML) Hole blocking layer
(HBL) Electron transport layer
(ETL) Electron injection layer
(EIL) cathode
Example 1-9 DS-205 a-NPB Inv 4, 7, 12, 14, 25, 28, 31, 36, or 38 + Ir (ppy) ₃ BCP Alq3 LiF Al Comparative Example 1 DS-205 a-NPB CBP + Ir (ppy) ₃ BCP Alq3 LiF Al

[ Evaluation example ]

For each organic EL device fabricated in Example 1-9 and Comparative Example 1, the luminous efficiency measured at a current density of 10 mA / cm 2 and the time (accelerated life) measured up to T = 97 (9000 nits) are shown in Table 2 below. Shown in

T = 97% / hr Voltage (V) Luminous Efficiency (cd / A) In-4 104 6.01 60.2 In-7 69 5.99 59.8 In-12 107 6.2 66.9 In-14 150 5.7 72.9 In-25 96 5.73 54.2 In-28 89 5.61 55.4 In-31 109 5.9 63.7 In-36 120 5.95 73.2 In-38 115 6.04 60.1 CBP 78 6.22 44.79

Looking at Table 2, it can be seen that the organic EL device using the compound according to the present invention as a host material is much better in terms of voltage and efficiency than the organic EL device using the conventional CBP, and especially the life is improved.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention. It is natural to belong.

Claims (5)

anode; cathode; And at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers comprises a compound represented by Formula 1 below: <Formula 1>

Where X is N, S or O; A means substituted or unsubstituted 6 to 40, monocyclic or fused polycyclic heterocycle, wherein at least the X-containing ring is 6 An aromatic ring of from 8 to 8; R ₁ to R ₁₀ are each independently hydrogen, deuterium, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C2-C40 alkynyl, substituted or unsubstituted C5-C40 aryl, substituted or unsubstituted heteroaryl having 5 to 40 nuclear atoms, substituted or unsubstituted C5-C40 aryloxy, substituted or unsubstituted C1-C40 alkyloxy, substituted or unsubstituted C5-C40 Arylamino, substituted or unsubstituted C5-C40 diarylamino, (substituted or unsubstituted C6-C40 aryl) C1-C40 alkyl, substituted or unsubstituted C3-C40 cycloalkyl, or substituted or unsubstituted nuclear atom 3 to 40 heterocycloalkyl, R ₅ and R ₆ may be linked to form a condensed ring. The method of claim 1, The organic layer is an organic electroluminescent device, characterized in that selected from the group consisting of a light emitting layer, an electron transport layer, a hole injection layer and a hole transport layer. The method of claim 1, The compound is an organic electroluminescent device, characterized in that the phosphorescent host material or a fluorescent host material. A compound of formula la or lb <Formula 1a>

<Formula 1b>

Where A, X, R ₁ to R ₁₀ are as defined in claim 1; R ₁₁ to R ₂₁ are each independently hydrogen, deuterium, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C2-C40 alkynyl, substituted or unsubstituted C5-C40 aryl, substituted or unsubstituted heteroaryl having 5 to 40 nuclear atoms, substituted or unsubstituted C5-C40 aryloxy, substituted or unsubstituted C1-C40 alkyloxy, substituted or unsubstituted C5-C40 Arylamino, substituted or unsubstituted C5-C40 diarylamino, (substituted or unsubstituted C6-C40 aryl) C1-C40 alkyl, substituted or unsubstituted C3-C40 cycloalkyl, or substituted or unsubstituted nuclear atom 3 to 40 heterocycloalkyl; L is a direct bond, substituted or unsubstituted C6-C40 aryl or substituted or unsubstituted heteroaryl having 6 to 40 nuclear atoms. The method of claim 4, wherein The L is a compound characterized in that it is selected from the group consisting of the structural formula of <Formula 2>

Where k, m and n are each independently integers ranging from 1 to 3; The plurality of Q ¹ are the same or different from each other, the plurality of Q ² are the same or different from each other, and the plurality of Q ³ are the same or different from each other; Q ¹ , Q ² and Q ³ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1-C40 alkyl; Substituted or unsubstituted C3-C40 cycloalkyl; Substituted or unsubstituted C2-C40 alkenyl; Substituted or unsubstituted C1-C40 alkoxy; Substituted or unsubstituted C1-C40 alkylamino; Substituted or unsubstituted C6-C40 aryl; Or a substituted or unsubstituted heteroaryl having 5 to 40 nuclear atoms, and these substituents may form a condensed ring of an aliphatic, aromatic, heteroaliphatic or heteroaromatic having adjacent groups with 6 to 40 nuclear atoms.