KR101804533B1

KR101804533B1 - Organic electroluminescent compound, producing method of the same and organic electroluminescent divice including the same

Info

Publication number: KR101804533B1
Application number: KR1020150107811A
Authority: KR
Inventors: 윤승수; 이현우; 김좌진; 김영석; 김세현; 김동영; 정수진; 김영관; 이호원
Original assignee: 성균관대학교산학협력단
Priority date: 2015-07-30
Filing date: 2015-07-30
Publication date: 2017-12-04
Also published as: KR20170014438A

Abstract

The present invention relates to a novel organic light emitting compound, a method for producing the same, and an organic electroluminescent device including the same.

Description

TECHNICAL FIELD The present invention relates to an organic electroluminescent compound, an organic electroluminescent compound, a method for producing the same, and an organic electroluminescent device including the electroluminescent compound.

Display has become an indispensable element of life, serving the existing information throughout the life, such as computers, television, and large advertisements. Recently, as the development of display and the improvement of quality of life have been improved, there is a demand for a versatile research and development having a complex function for improving not only information providing function but also life quality. As a result, OLED (Organic Light-Emitting Diode) presents many possibilities and various indicators in future-oriented researches such as flexible displays and wearable displays using thin and light materials. The OLED display is a self-luminous display device that can be lightweight and thin, has excellent contrast ratio and viewing angle, and has a high response speed. In addition, OLED devices have many advantages in manufacturing flexible and transparent devices because OLED devices have advantages in that they do not have a backlight that occupies a large volume in an LCD as compared to an LCD (liquid crystal display), which is an important material together with OLED as a display material .

Organic electroluminescent devices (OLEDs) were first fabricated in 1963 by W. Helfrich, M. Pope et al., Using anthracene single crystals. In 1965, W. Helfrich [W. Helfrich and WG Schneider, Phys. Rev. Lett. 14, 229 (1965)]. Later in the late 1980s, Alq _3, which was found at Eastman Kodak Company, opened up more possibilities for practical application to organic thin films. Alq ₃ was discovered by Tang and Van-Slyke, and is a material exhibiting luminescence in the green region as well as an excellent electron transporting ability according to the quinoline structure of Alq ₃ itself. A variety of techniques have been developed to display the three primary colors of light, red, green, and blue. Red, green, and blue organic light emitting materials having excellent characteristics are required to realize a full color display on a display. However, Has a disadvantage in that color purity and lifetime characteristics are inferior to red and green luminescent materials. In order to solve this problem, it is possible to improve the efficiency and color purity by reducing the intermolecular interaction by introducing a large functional group between the light emitting materials in the material side and the device side, and by changing the light emitting core and the side group, molecular orbital / LUMO (lowest unoccupied molecular orbital) to facilitate charge injection and migration and to control the wavelength of light (Korean Patent Registration No. 10-1290015). Currently, OLEDs are mainly used in mobile phones, wrist watches, TVs, etc. However, if such flexible and wearable OLED characteristics are well developed, it will become an indispensable element in everyday life such as Internet of things, .

The present invention provides a novel organic light emitting compound, a method for producing the same, and an organic electroluminescent device including the same.

However, the problems to be solved by the present invention are not limited to the problems described above, and other problems not described can be clearly understood by those skilled in the art from the following description.

A first aspect of the invention provides an organic electroluminescent compound represented by Formula 1:

[Chemical Formula 1]

In the above formulas,

R ₁ is C ₁ -C ₆ alkyl which may be substituted, or which may be substituted,

R ₂ is a single bond; A 5-membered unsaturated or aromatic ring which may be substituted, a 6-membered unsaturated or aromatic ring which may be substituted, a 5-membered unsaturated or aromatic heterocyclic ring which may be substituted, and a A 6-membered unsaturated or aromatic heterocyclic ring, or a polycyclic ring fused with two or more rings selected from the above group,

Wherein said heterocycle comprises at least one member selected from the group consisting of N, O and S,

Said substitution being substituted by C ₁ -C ₆ alkyl, aryl, or anthracene.

The second aspect of the present invention relates to a process for preparing a compound represented by the general formula (2) in the presence of a palladium catalyst in the presence of a halogen-substituted 5-membered aromatic heterocyclic compound, a halogen-substituted 6-membered aromatic or aromatic heterocyclic compound or a halogen-substituted polycyclic aromatic ring compound &Lt; / RTI > with a compound of formula < RTI ID = 0.0 >

(2)

In the above formulas,

R ₁ is C ₁ -C ₆ alkyl which may be substituted, or aryl which may be substituted,

Said substitution being substituted by C ₁ -C ₆ alkyl or aryl.

The third aspect of the present invention provides an organic electroluminescent device comprising the organic electroluminescent compound according to the present invention.

In the present application, the introduction of a functional group, for example, a methyl group, which prevents intermolecular interactions to a fluorene group increases the stability in terms of improvement in thermal stability and stability in terms of morphology and, due to the structural characteristic of the compound, And can provide novel compounds with controlled wavelength and properties. Further, by adjusting the bonding position between the anthracene derivatives with an aromatic ring to control the luminescent property and by introducing the functional group which attracts electrons to the aromatic ring, the emission wavelength is controlled by changing the energy interval, thereby improving the color purity of the organic electroluminescent device have. More specifically, the energy levels of the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) are adjusted to enable the blue light emission required for a full color display. Further, the electron mobility can be changed to control the light emission characteristics of the device using these light emitting materials.

The organic electroluminescent compound of the present invention has high luminescence efficiency and high color purity and can contribute to the OLED industry such as flexible display and illumination by applying it to an organic electroluminescent device and an organic photonic device for solar power generation .

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

Hereinafter, embodiments and examples of the present invention will be described in detail with reference to the accompanying drawings, which will be readily apparent to those skilled in the art to which the present invention pertains.

It should be understood, however, that the present invention may be embodied in many different forms and is not limited to the embodiments and examples described herein. In order to clearly illustrate the present invention, parts not related to the description are omitted, and similar parts are denoted by like reference characters throughout the specification.

Throughout this specification, when a member is "on " another member, it includes not only when the member is in contact with the other member, but also when there is another member between the two members.

Throughout this specification, when an element is referred to as "including " an element, it is understood that the element may include other elements as well, without departing from the other elements unless specifically stated otherwise. The terms "about "," substantially ", etc. used to the extent that they are used throughout the specification are intended to be taken to mean the approximation of the manufacturing and material tolerances inherent in the stated sense, Accurate or absolute numbers are used to help prevent unauthorized exploitation by unauthorized intruders of the referenced disclosure. The word " step (or step) "or" step "used to the extent that it is used throughout the specification does not mean" step for.

Throughout this specification, the term "combination thereof" included in the expression of the machine form means one or more combinations or combinations selected from the group consisting of the constituents described in the expression of the machine form, And the like.

Throughout this specification, the description of "A and / or B" means "A or B, or A and B".

Throughout this specification, the term "aromatic ring" refers to a C _6-30 aromatic hydrocarbon ring group such as phenyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenylenyl, perylenyl Means an aromatic ring such as benzyl, benzyl, benzyl, benzyl, benzyl, benzyl, benzyl, benzyl, benzyl, benzyl, As the aromatic ring containing a hetero element, for example, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, Thienyl, and pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, triazine rings, pyrrolidinyl rings, pyrrolidinyl rings, pyrrolidinyl rings, An indole ring, a quinoline ring, an acridine ring , Pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole Means an aromatic heterocyclic group formed from a ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, dibenzofuran ring.

Throughout this specification, the term " fused " means that, with respect to two or more rings, at least one or more adjacent atoms are included in both rings.

Throughout the specification, the term "alkyl" may be linear or branched, including saturated or unsaturated C ₁ -C ₆ alkyl, such as methyl, ethyl, propyl, butyl, pentyl, But is not limited to, all possible isomers.

Throughout the specification of the present application, the term " halogen " may include, but is not limited to, Group 17 elements of the periodic table, for example, F, Cl, Br,

[Chemical Formula 1]

In the above formulas,

R ₁ is C ₁ -C ₆ alkyl which may be substituted or aryl which may be substituted,

The substitution may be substituted by C ₁ -C ₆ alkyl, aryl, or anthracene.

In one embodiment herein, R < ₁ > may be methyl or phenyl, but is not limited thereto.

In an embodiment of the present invention, R ₂ is a single bond or a group selected from the group consisting of a 6-membered aromatic ring, an optionally substituted 5-membered or 6-membered aromatic heterocycle, fluorene, triphenylamine Or a polycyclic ring fused with two or more rings selected from the above-mentioned group, but may not be limited thereto. The heterocycle may include at least one member selected from the group consisting of N, O and S, and the substitution may be substituted by C ₁ -C ₆ alkyl, aryl, or indenoanthracene, but is not limited thereto.

In one embodiment of the invention, the organic electroluminescent compounds according to the present application is a 9,9-dimethyl-9,10-diphenyl anthracene -9 H - fluorenyl the introduction of fluorene structure 13,13- dimethyl diphenyl -6,11- -13 H -indeno [2,1- b ] anthracene derivatives, but the present invention is not limited thereto. In order to minimize the influence between the light emitting materials, a functional group that inhibits intermolecular interaction at the 9-position of the fluorene group, for example, two methyl groups, is introduced to improve the thermal stability and increase stability in terms of morphology . Further, 13,13- dimethyl -6,11- diphenyl -13 H - indeno [2,1- b] By adjusting the coupling positions of the anthracene derivatives of an aromatic ring, and adjusting the light emission characteristics, the electron to an aromatic ring The color purity of the organic electroluminescent device can be improved by controlling the emission wavelength by changing the energy interval by introducing the functional group to be pulled. Furthermore, the emission wavelength can be controlled by introducing a hetero atom which is a substituent which attracts electrons to a phenyl ring such as pyridine. More specifically, the energy level of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) can be controlled to enable blue light emission required for a full color display. Further, by changing the electron mobility, the luminescent characteristics of the device using these luminescent materials can be controlled.

In one embodiment of the present invention, the organic light emitting compound may include, but is not limited to, the following compounds:

The second aspect of the invention herein provides a process for the preparation of a compound represented by formula 2 in the presence of a palladium catalyst in the presence of a halogen-substituted 5-membered aromatic heterocyclic compound, a halogen-substituted 6-membered aromatic or aromatic heterocyclic compound or a halogen- Lt; RTI ID = 0.0 > R, < / RTI >

(2)

In the above formulas,

The substitution may be substituted by C ₁ -C ₆ alkyl or aryl.

In one embodiment of the present invention, the polycyclic aromatic ring compound may include, but is not limited to, a compound selected from the group consisting of naphthalene, anthracene, fluorene, carbazolyl, and triphenylamine.

In one embodiment of the present invention, the aromatic heterocyclic compound may include at least one selected from the group consisting of N, O and S, but may not be limited thereto.

In one embodiment of the present invention, the organic electroluminescent device may include, for example, ITO (180 nm) / 2-TNATA (60 nm) / NPB (20 nm) / organic luminescent compound (30 nm) / Bphen ) / Liq (2 nm) / Al (100 nm), but the present invention is not limited thereto. The organic electroluminescent device can be manufactured as follows: A transparent electrode ITO (indium-tin-oxide) thin film (sheet resistance 12 Ω / square) obtained from an organic EL glass is sequentially used with acetone, methanol, After ultrasonic cleaning, store in isopropyl alcohol for 20 minutes before use. 2-TNATA (4,4 ', 4 "-tris [2-naphthyl (phenyl) amino] triphenylamine) was added to the cell in the vacuum deposition equipment, After evacuation until the degree of vacuum in the chamber reaches 5.0 x 10 < ^-7 > Torr, a current is applied to the cell to evaporate 2-TNATA to deposit a hole injection layer of about 60 nm thickness on the ITO substrate. A hole transport layer having a thickness of 20 nm is deposited by evaporating NPB (4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl) under the conditions described in The organic light emitting compound was evaporated at a rate of 1.0 A / sec to deposit a light emitting layer having a thickness of about 30 nm on the hole transport layer. Then, Bphen (4,7-diphenyl-1,10-phenanthroline) And Liq (lithium quinolate) are sequentially evaporated to deposit an electron transport layer and an electron injection layer each having a thickness of about 30 nm and a thickness of about 2 nm, respectively.

The organic light emitting compounds according to aspects of the present invention may be applied to all of the first and second aspects of the present invention, but the present invention is not limited thereto.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the scope of the present invention is not limited by these Examples.

[ Example ]

Example 1: 13 , 13-dimethyl-2- (13,13-dimethyl-6,11-diphenyl-13 H - Indeno [2,1- b ]anthracene Yl) -6,11-diphenyl-13 H - indeno [2,1- b ] Anthracene ( 1) of synthesis

1- (1): methyl 5- Bromo -2- (9,10- Diphenylanthracene Yl) Benzoate synthesis

To a stirred solution of 1.03 g (1 eq, 3.05 mmol) of methyl 5-bromo-2-iodobenzoate, 1.20 g (1.05 eq, 3.20 mmol) of 9,10-diphenylanthracen- 129 mg (0.04 eq, 0.12 mmol) of kiss (triphenylphosphine) palladium (0) was placed in a reaction vessel, vacuum dried and then filled with nitrogen gas. 40 ml of toluene was added to the flask to dissolve the compounds, and 20 ml of ethanol and 20 ml (2.0 g) of sodium carbonate aqueous solution (10.0 eq, 30.5 mmol) were added. The mixture was refluxed for 3 hours at 120 ° C and stirred. After completion of the reaction, the reaction mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. Dried over magnesium sulfate, filtered through celite, and then subjected to column chromatography to obtain 2.17 g of methyl 5-bromo-2- (9,10-diphenylanthracene-6-yl) benzoate (yield = 66% Respectively.

1- (2): 2- Bromo -13,13-dimethyl-6,11-diphenyl-13 H - Indeno [2,1- b ] Anthracene synthesis

2.17 g (1 eq, 3.99 mmol) of methyl 5-bromo-2- (9,10-diphenylanthracene-6-yl) benzoate obtained in the above 1- (1) was placed in a reaction vessel, I filled the gas. 70 ml of THF was added to the reaction vessel to dissolve the compounds, and 6.5 ml (5 eq, 19.96 mmol) of 3.0 M methyl magnesium bromide aqueous solution was added thereto. The mixture was refluxed at room temperature for 3 hours and stirred. After completion of the reaction, the reaction solution was slowly poured into a beaker containing the ammonium chloride solution and stirred for 10 minutes. It was then washed with distilled water and the organic layer was extracted with ethyl ether. After drying over magnesium sulfate and filtration through celite, the compound obtained via column chromatography was dried. Then, 3 ml of methylene chloride was added, and the mixture was stirred for 5 minutes. Then, 5 ml of methanesulfonic acid was slowly added dropwise thereto, and the mixture was stirred at room temperature. After completion of the reaction extracted with ethyl acetate and column chromatography, the compound 2-bromo -13,13- through -6,11- dimethyl diphenyl -13 H - indeno [2,1- b] anthracene 1.12 g (yield = 72%).

1- (3): 4,4,5,5- Tetramethyl -2- (13, 13-dimethyl-7, 12-diphenyl-13 H - Indeno [2,1- b ]anthracene -2-yl) -1,3,2-dioxaborolane

The 1 - (2) 2-Bromo -13,13- -6,11- dimethyl diphenyl -13 H obtained in step-indeno [2,1- b] anthracene 1.1 g (1 eq, 2.09 mmol ) to The resultant was placed in a reaction vessel, vacuum-dried, and filled with nitrogen gas. 110 ml of THF was added to the reaction vessel to dissolve the compounds. Then, 1.9 ml (1.5 eq, 2.97 mmol) of 1.6 M n-BuLi aqueous solution was slowly added dropwise at -78 ° C and stirred for 1 hour. After that, 0.50 ml (1.5 eq, 2.97 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was quickly added and stirred for 30 minutes. Then, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was washed with distilled water and the organic layer was extracted with ethyl ether. Compound dried with magnesium sulfate, through a column chromatography and then filtered through celite 4,4,5,5-Tetramethyl-2- (13,13- dimethyl-7,12-diphenyl -13 H - indeno [2,1- b ] anthracene-2-yl) -1,3,2-dioxaborane (yield: 67%).

1- (4): 13,13-Dimethyl-2- (13,13-dimethyl-6,11-diphenyl-13 H - Indeno [2,1- b ] Ant Lachen-2-yl) -6,11-diphenyl-13 H - indeno [2,1- b ] Synthesis of Anthracene (1)

Indeno [2,1- b] anthracene-1-a (3) 4,4,5,5-Tetramethyl-2- (13,13- dimethyl-7,12-diphenyl -13 H obtained in step - 0.20 g (1.1 eq, 0.349 mmol) of 2-bromo-13,13-dimethyl-6,11-diazabicyclo [ diphenyl -13 H - indeno [2,1- b] anthracene 0.17 g (1 eq, 0.317 mmol ), tetrakis (triphenylphosphine) palladium (0) 36 mg (0.04 eq , 0.032 mmol) and aliquat 336 10 mg (0.1 eq, 0.0317 mmol) was charged into a reaction vessel, vacuum-dried and then filled with nitrogen gas. 20 ml of toluene was placed in the reaction vessel to dissolve the compounds, and then 1.6 ml (2.0 mmol) of a 2.0 M aqueous potassium carbonate solution (10.0 eq, 3.17 mmol) was added. The mixture was refluxed at 120 ° C for 3 hours and stirred. After completion of the reaction, the reaction mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. After drying over magnesium sulfate and filtering through celite, the compound obtained by column chromatography was recrystallized from methylene chloride and n-hexane to obtain the final compound 13,13-dimethyl-2- (13,13-dimethyl- 11-diphenyl -13 H - indeno [2,1- b] anthracene-2-yl) -6,11- diphenyl -13 H - indeno [2,1- b] anthracene 0.16 g (yield = 57 %).

_{(CDCl 3, 500 MHz, δ} ): 7.78 (s, 4H), 7.76 (s, 1H), 7.74 (s, 1H), 7.61-7.59 (m, 8H), 7.57-7.54 (m, 11H), 7.48 (d, J = 5.9 Hz, 4H), 7.47-7.46 (m, 5H), 7.29-7.27

APCI-MS (m / z): 967 [M +] <

Example 2: 1 ,4- Bis (13,13-dimethyl-6,11-diphenyl-13 H - Indeno [2,1- b ]anthracene Yl) benzene (2) Synthesis of

0.1 g (1 eq, 0.424 mmol) of 1,4-dibromobenzene and 4,4,5,5-tetramethyl-2- (13,13-dimethyl 7,12-diphenyl -13 H - indeno [2,1- b] anthracene-2-yl) 1,3,2-dioxa-view it is 0.51 g (2.1 eq, 0.890 mmol ), tetrakis 48 mg (0.1 eq, 0.042 mmol) of triphenylphosphine (triphenylphosphine) palladium (0) and 34 mg (0.2 eq, 0.084 mmol) of aliquat 336 were placed in a reaction vessel and vacuum dried and then filled with nitrogen gas. And 50 ml of toluene were placed in the reaction vessel to dissolve the compounds. 4.3 ml (20.0 eq, 8.48 mmol) of 2.0 M potassium carbonate aqueous solution was added thereto, and the mixture was refluxed for 3 hours at 120 ° C and stirred. After completion of the reaction, the reaction mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. After drying over magnesium sulfate and filtering through celite, the compound obtained by column chromatography was recrystallized from methylene chloride and n-hexane to obtain the final compound 1,4-bis (13,13-dimethyl-6,11-diphenyl -13 H - indeno [2,1- b] anthracene-2-yl) benzene 0.23 g (yield = 56%).

_{(CDCl 3, 500 MHz, δ} ): 7.79 (s, 1H), 7.78 (s, 3H), 7.66 (s, 1H), 7.61-60 (m, 5H), 7.60-7.59 (m, 6H), 7.56 (M, 2H), 7.41 (m, 4H), 7.54 (m,

APCI-MS (m / z): 344 [M < + >] [

Example 3: 1 , 3- Bis (13,13-dimethyl-6,11-diphenyl-13 H - Indeno [2,1- b ]anthracene Yl) benzene ( 3) of synthesis

0.1 g (1 eq, 0.424 mmol) of 1,3-dibromobenzene and 4,4,5,5-tetramethyl-2- (13,13-dimethyl 7,12-diphenyl -13 H - indeno [2,1- b] anthracene-2-yl) 1,3,2-dioxa-view it is 0.51 g (2.1 eq, 0.890 mmol ), tetrakis 48 mg (0.1 eq, 0.042 mmol) of triphenylphosphine palladium (0) and 34 mg (0.2 eq, 0.084 mmol) of aliquat 336 were charged in a reaction vessel, dried in vacuo, and then filled with nitrogen gas. And 50 ml of toluene were placed in the reaction vessel to dissolve the compounds. 4.3 ml (20.0 eq, 8.48 mmol) of 2.0 M potassium carbonate aqueous solution was added thereto, and the mixture was refluxed for 3 hours at 120 ° C and stirred. After completion of the reaction, the reaction mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. After drying over magnesium sulfate and filtration through celite, the compound obtained by column chromatography was recrystallized from methylene chloride and n-hexane to obtain the final compound 1,3-bis (13,13-dimethyl-6,11-diphenyl -13 H -indeno [2,1- b ] anthracen-2-yl) benzene (yield = 54%).

^{_{1 H-NMR: (CDCl 3}} , 500 MHz, δ): 7.79 (s, 3H), 7.78 (s, 2H), 7.61 (s, 4H), 7.60 (s, 5H), 7.57-7.56 (m, 4H ), 7.55-7.54 (m, 7H), 7.52 (s, 3H), 7.48-7. 45 (m, 9H), 7.30-7.27

APCI-MS (m / z): 967 [M +] <

Example 4: 2 , 6- Bis (13,13-dimethyl-6,11-diphenyl-13 H - Indeno [2,1- b ]anthracene Yl) pyridine ( 4) of synthesis

0.1 g (1 eq, 0.422 mmol) of 2,5-dibromopyridine and 4,4,5,5-tetramethyl-2- (13,13-dimethyl 7,12-diphenyl -13 H - indeno [2,1- b] anthracene-2-yl) 1,3,2-dioxa-view it is 0.51 g (2.1 eq, 0.880 mmol ), tetrakis (0.2 eq, 0.084 mmol) of aliquat 336 and 49 mg (0.1 eq, 0.042 mmol) of triphenylphosphine (triphenylphosphine) palladium (0) were placed in a reaction vessel, vacuum dried and then filled with nitrogen gas. And 50 ml of toluene were placed in the reaction vessel to dissolve the compounds. 4.3 ml (20.0 eq, 8.44 mmol) of 2.0 M potassium carbonate aqueous solution was added thereto, and the mixture was refluxed for 3 hours at 120 ° C and stirred. After completion of the reaction, the reaction mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. After drying over magnesium sulfate and filtration through celite, the compound obtained by column chromatography was recrystallized from methylene chloride and n-hexane to obtain the final compound 2,6-bis (13,13-dimethyl-6,11-diphenyl -13 H -indeno [2,1- b ] anthracen-2-yl) pyridine (yield = 57%).

^{_{1 H-NMR: (CDCl 3}} , 500 MHz, δ): 7.80 (d, J = 3.2Hz, 2H), 7.78 (s, 2H), 7.67 (t, J = 6.3Hz, 3H), 7.63-7.59 ( (m, 8H), 7.29-7.27 (m, 4H), 1.23 (s, 12H), 7.50-7.

APCI-MS (m / z): 968 [M ⁺ ] &^lt;

Experimental Example 1: Measurement of organic electroluminescence characteristics

A glass substrate coated with an indium tin oxide (ITO) thin film was used for OLED manufacturing. The sheet resistance of the glass substrate was 12 Ω / square and the thickness was 180 nm. The ITO-coated glass was ultrasonically washed in an ultrasonic bath in the order of acetone, methyl alcohol, and distilled water, then left in isopropyl alcohol for 20 minutes and dried using a N ₂ gas gun. The substrate was treated with an O ₂ plasma in an Ar atmosphere. The ITO-coated glass was mounted on a substrate folder of a vacuum deposition equipment and 2-TNATA was placed in a cell in a vacuum deposition equipment. After evacuation until the degree of vacuum in the chamber reached 5.0 x 10 < ^-7 > Torr, a current was applied to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate. NPB (4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl) was then evaporated under the same conditions to deposit a 20 nm thick hole transport layer. Also, the organic electroluminescent compound (1-4) synthesized as in the above embodiment was evaporated at a rate of 1.0 Å / sec in the vacuum deposition apparatus to deposit a 30 nm thick emission layer on the hole transport layer. Subsequently, Bphen (4,7-diphenyl-1,10-phenanthroline) and Liq (lithium quinolate) were sequentially evaporated under similar conditions to deposit 30 nm and 2 nm thick electron transport layers and electron injection layers, respectively Respectively. All organic materials and metals were deposited under high vacuum (5.0 x 10 < ^-7 > Torr). Then, an Al cathode was deposited by using other vacuum deposition equipment to manufacture an OLED. The OLED according to this experimental example was prepared in the following sequence: ITO (180 nm) / 4,4 ', 4''' -tris [2-naphthyl (phenyl) amino] triphenylamine HIL) (60 nm) / 4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl (NPB, HTL) 30 nm, EML) / 4,7-diphenyl-1,10-phenanthroline (Bphen, ETL) (30 nm) / lithium quinolate (Liq) (2 nm) / Al (100 nm). The emission characteristics and the light emission (EL) spectrum of the OLED were measured using a Keithley 2400 source measurement unit and a CS1000A spectrophotometer, and the results are shown in Table 1.

It will be understood by those of ordinary skill in the art that the foregoing description of the embodiments is for illustrative purposes and that those skilled in the art can easily modify the invention without departing from the spirit or essential characteristics thereof. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive. For example, each component described as a single entity may be distributed and implemented, and components described as being distributed may also be implemented in a combined form.

The scope of the present invention is defined by the appended claims rather than the detailed description, and all changes or modifications derived from the meaning and scope of the claims and their equivalents should be interpreted as being included in the scope of the present invention .

Claims

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

In the above formulas,
R < ₁ > is methyl or phenyl,
R ₂ is a single bond; Or a 6-membered aromatic ring.

delete

A process for preparing an organic luminescent compound according to claim 1, comprising reacting a compound represented by formula (2) with a halogen-substituted single bond compound or a halogen-substituted 6-membered aromatic ring compound in the presence of a palladium catalyst:
(2)

In the above formulas,
R < ₁ _> is methyl or phenyl.

delete

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