KR101219492B1 - Compound Containing 5-Membered Heterocycle And Organic Electronic Element Using The Same, Terminal Thereof - Google Patents

Compound Containing 5-Membered Heterocycle And Organic Electronic Element Using The Same, Terminal Thereof Download PDF

Info

Publication number
KR101219492B1
KR101219492B1 KR20090123544A KR20090123544A KR101219492B1 KR 101219492 B1 KR101219492 B1 KR 101219492B1 KR 20090123544 A KR20090123544 A KR 20090123544A KR 20090123544 A KR20090123544 A KR 20090123544A KR 101219492 B1 KR101219492 B1 KR 101219492B1
Authority
KR
South Korea
Prior art keywords
substituted
group
unsubstituted
carbon atoms
oxygen
Prior art date
Application number
KR20090123544A
Other languages
Korean (ko)
Other versions
KR20110066766A (en
Inventor
김대성
박정환
박용욱
김기원
정화순
변지훈
최대혁
김동하
Original Assignee
삼성디스플레이 주식회사
덕산하이메탈(주)
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 삼성디스플레이 주식회사, 덕산하이메탈(주) filed Critical 삼성디스플레이 주식회사
Priority to KR20090123544A priority Critical patent/KR101219492B1/en
Publication of KR20110066766A publication Critical patent/KR20110066766A/en
Application granted granted Critical
Publication of KR101219492B1 publication Critical patent/KR101219492B1/en

Links

Images

Abstract

The present invention provides a compound containing an five-membered hetero ring, an organic electric device using the same, and a terminal thereof.
Organic electric element, hetero ring

Description

Compound containing five-membered heterocyclic ring and organic electronic device using the same, and terminal thereof {Compound Containing 5-Membered Heterocycle And Organic Electronic Element Using The Same, Terminal Thereof}

The present invention relates to a compound comprising a five-membered hetero ring, an organic electric device using the same, and a terminal thereof.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like, depending on their functions. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be classified. In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as the light emitting material in order to increase the light emitting efficiency through the light emitting layer. The principle is that when a small amount of dopant having an energy band gap smaller than that of a host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing 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.

In order to fully exhibit the excellent characteristics of the above-described organic electroluminescent device, a material forming the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. Although this should be preceded, the development of a stable and efficient organic material layer for an organic electric element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.

The present inventors have found a compound comprising two or more five-membered heterocycles having a novel structure, and the application of the compound to organic electroluminescent devices can significantly improve the luminous efficiency, stability and lifetime of the device. Revealed.

Accordingly, an object of the present invention is to provide a compound containing a novel five-membered hetero ring, an organic electric device using the same, and a terminal thereof.

In one aspect, the present invention provides a compound of the formula

Figure 112009076810511-pat00001

The present invention provides hole injection materials, hole transport materials, light emitting materials and / or electron transport materials suitable for fluorescence and phosphorescent devices of all colors, such as red, green, blue, white, etc., depending on the compound comprising two or more five-membered hetero rings. It is useful as a host material for phosphorescent dopants of various colors.

The present invention also provides an organic electronic device using the compound having the above formula and a terminal including the organic electronic device.

Compounds containing two or more five-membered heterocycles can play various roles in organic electronic devices and terminals, and are suitable for injection and hole transport materials suitable for fluorescent and phosphorescent devices of all colors such as red, green, blue, and white. It is useful as a light emitting material and / or an electron transporting material, and as a host material of phosphorescent dopants of various colors.

Hereinafter, some embodiments of the present invention will be described in detail with reference to exemplary drawings. In adding reference numerals to the components of each drawing, it should be noted that the same reference numerals are assigned to the same components as much as possible even though they are shown in different drawings. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In addition, in describing the component of this invention, terms, such as 1st, 2nd, A, B, (a), (b), can be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements. When a component is described as being "connected", "coupled", or "connected" to another component, the component may be directly connected to or connected to the other component, It should be understood that an element may be "connected," "coupled," or "connected."

In one aspect, the present invention provides a compound of Formula 1 below.

Figure 112009076810511-pat00002

In the formula 1,

(1) R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are each independently of each other a hydrogen atom, a halogen atom, a cyan No group, thiol group, substituted or unsubstituted C1-C50 alkyl group, substituted or unsubstituted C1-C50 alkoxy group, substituted or unsubstituted C1-C50 alkenyl group, substituted or unsubstituted C5-C5 Substitutes containing at least one aryl group of 60, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) Or a substituted or unsubstituted C 5 to C 5 containing at least one unsubstituted heteroalkyl group having 1 to 50 carbon atoms or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si). A heteroaryl group having 5 to 60 carbon atoms or at least one heteroaryl group containing 60 (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si); Is the time.

(2) R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 and R 9 , R 10 , R 11 and R 12 May combine with adjacent groups to form a ring. That is, R 1 to R 12 may combine with adjacent groups to form a saturated or unsaturated ring.

(3) X is sulfur (S) or oxygen (O).

(4) Y represents a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, a thiol group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon number 5 To 60 arylene group, substituted or unsubstituted aryl group having 5 to 60 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen (O), phosphorus ( A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or at least one of P) and silicon (Si) or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si); Substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms containing at least one or at least one containing sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) Or an unsubstituted heteroaryloxy group having 5 to 60 carbon atoms.

(5) n is an integer of 1 or 2.

(6) The compound having the formula (1) can be used in a soluble process.

In another aspect, the present invention provides a compound of Formula 2 below.

Figure 112009076810511-pat00003

In another aspect, the present invention provides a compound of formula 3 below.

Figure 112009076810511-pat00004

In Formulas 2 and 3, X and Y may be the same as in Formula 1.

In another aspect, the present invention provides compounds of formulas 4a and 4b below.

Figure 112009076810511-pat00005

In Chemical Formula 4,

(7) R 13 is a hydrogen atom, a halogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms or sulfur It is a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms containing at least one of (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si).

(8) Ar 1 and Ar 2 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon number 5 to A substitution containing at least one arylene group of 60, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) or Unsubstituted heteroaryl group having 5 to 60 carbon atoms, X is sulfur (S) or oxygen (O).

In another aspect, the present invention provides a compound of formula 5 below.

Figure 112009076810511-pat00006

In Chemical Formula 5,

(9) R 14 and R 15 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms or sulfur (S), nitrogen Substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms containing at least one (N), oxygen (O), phosphorus (P) and silicon (Si),

(10) Z independently represents a single bond, or -O-, -S-, -CO-, -SO 2- , -NR 16- , -PR 17- , -SiR 18 R 19- , substituted or unsubstituted An arylene group having 5 to 60 carbon atoms in the ring, wherein R 16 to R 19 are each independently a hydrogen atom, a halogen atom, a cyano group, a thiol group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted group An alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S ), A substituted or unsubstituted heteroalkyl group having 1 to 50 carbon atoms or at least one of nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) or sulfur (S), nitrogen (N), Substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms or at least one containing oxygen (O), phosphorus (P) and silicon (Si) or sulfur (S), nitrogen (N) is a substituted or unsubstituted C5-C60 heteroaryloxy group containing at least one of oxygen (O), phosphorus (P) and silicon (Si), and (3) X is sulfur (S) or Oxygen (O).

In this case, the compounds represented by Formulas 2 to 5 may be used in a solution process.

Specific examples of the compounds belonging to Formulas 1 to 5 which are compounds including two or more five membered hetero rings according to one embodiment of the present invention include the compounds of Formula 6 below, but the present invention is not limited thereto.

Figure 112009076810511-pat00007

Figure 112009076810511-pat00008

Figure 112009076810511-pat00009

Figure 112009076810511-pat00010

Figure 112009076810511-pat00011

Figure 112009076810511-pat00012

Figure 112009076810511-pat00013

Figure 112009076810511-pat00014

Figure 112009076810511-pat00015

Figure 112009076810511-pat00016

Figure 112009076810511-pat00017

Figure 112009076810511-pat00018

Figure 112009076810511-pat00019

Figure 112009076810511-pat00020

Figure 112009076810511-pat00021

Figure 112009076810511-pat00022

Figure 112009076810511-pat00023

Figure 112009076810511-pat00024

Figure 112009076810511-pat00025

Figure 112009076810511-pat00026

Figure 112009076810511-pat00027

Figure 112009076810511-pat00028

Figure 112009076810511-pat00029

Figure 112009076810511-pat00030

Figure 112009076810511-pat00031

Figure 112009076810511-pat00032

Figure 112009076810511-pat00033

Figure 112009076810511-pat00034

Figure 112009076810511-pat00035

Figure 112009076810511-pat00036

Figure 112009076810511-pat00037

Figure 112009076810511-pat00038

Figure 112009076810511-pat00039

Figure 112009076810511-pat00040

Figure 112009076810511-pat00041

Figure 112009076810511-pat00042

Figure 112009076810511-pat00043

Figure 112009076810511-pat00044

Figure 112009076810511-pat00045

Figure 112009076810511-pat00046

Figure 112009076810511-pat00047

Various organic electric devices exist in which compounds including two or more five-membered hetero rings described with reference to Chemical Formulas 1 to 6 are used as the organic material layer. Examples of the organic electroluminescent device in which compounds including two or more five-membered hetero rings described with reference to Chemical Formulas 1 to 6 may be used include, for example, an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC) drum, Organic transistors (organic TFTs), photodiodes, organic lasers, laser diodes, and the like.

One example of an organic electroluminescent device to which compounds including two or more five-membered hetero rings described with reference to Chemical Formulas 1 to 6 may be applied, but the present invention is not limited thereto. The compound including two or more five-membered hetero rings described above may be applied to the organic electric device.

Another embodiment of the present invention is an organic electric device comprising a first electrode, a second electrode and an organic material layer disposed between the electrodes, wherein at least one of the organic material layer of the organic electric field comprising the compounds of Formula 1 to 6 Provided is a light emitting device.

1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.

The organic light emitting device according to another embodiment of the present invention, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer And a structure known in the art using conventional manufacturing methods and materials in the art, except that at least one layer of the organic material layer including the electron injection layer is formed to include the compounds of Formulas 1 to 6. It can be prepared as.

The structure of the organic light emitting display device according to another embodiment of the present invention is illustrated in FIGS. 1 to 6, but is not limited thereto. In this case, reference numeral 101 denotes a substrate, 102 an anode, 103 a hole injection layer (HIL), 104 a hole transport layer (HTL), 105 a light emitting layer (EML), 106 an electron injection layer (EIL), 107 an electron transport layer ( ETL), 108 represents a negative electrode. Although not shown, the organic light emitting diode may further include a hole blocking layer (HBL) that prevents the movement of holes, an electron blocking layer (EBL) that prevents the movement of electrons, and a protective layer. The protective layer may be formed to protect the organic material layer or the cathode at the uppermost layer.

In this case, the compound including two or more five-membered hetero rings described with reference to Chemical Formulas 1 to 12 may be included in one or more of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer. Specifically, the compound including two or more five-membered heterocyclic rings described with reference to Chemical Formulas 1 to 12 includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, a protective layer It may be used in place of one or more, or may be used in conjunction with them to form a layer. Of course, the organic layer may be used not only in one layer but also in two or more layers.

Compounds including two or more five-membered heterocycles described with reference to Chemical Formulas 1 to 6 may play various roles in organic electronic devices and terminals, and may be used in fluorescent and phosphorescent devices of all colors such as red, green, blue, and white. It is useful as a suitable hole injection material, hole transport material, luminescent material and / or electron transport material and can be used as a host material for phosphorescent dopants of various colors.

For example, the organic light emitting device according to another embodiment of the present invention is a metal having a metal or conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation An oxide or an alloy thereof is deposited to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. Can be prepared by

In addition to the above method, an organic electronic device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer may be formed using a variety of polymer materials by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process or a thermal transfer process, Layer.

The organic electroluminescent device according to another embodiment of the present invention may form an organic layer, for example a light emitting layer, by a soluble process of a compound containing two or more five-membered hetero rings described above.

The substrate is a support of the organic light emitting device, and a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet, or the like can be used.

An anode is positioned over the substrate. This anode injects holes into the hole injection layer located thereon. As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto. .

The hole injection layer is located on the anode. The conditions required for the material of the hole injection layer are high hole injection efficiency from the anode, it should be able to transport the injected holes efficiently. This requires a small ionization potential, high transparency to visible light, and excellent hole stability.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is positioned on the hole injection layer. The hole transport layer receives holes from the hole injection layer and transports the holes to the organic light emitting layer located thereon, and serves to prevent high hole mobility, hole stability, and electrons. In addition to these general requirements, when applied for vehicle body display, heat resistance to the device is required, and a material having a glass transition temperature (Tg) of 70 ° C. or higher is preferable. The materials satisfying these conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene, silicon germanium Oxide compounds, silicon-based arylamine compounds, and the like.

The organic light emitting layer is positioned on the hole transport layer. The organic light emitting layer is a layer for emitting light by recombination of holes and electrons injected from the anode and the cathode, respectively, and is made of a material having high quantum efficiency. The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.

Substances or compounds that satisfy these conditions include Alq3 for green, Balq (8-hydroxyquinoline beryllium salt) for blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'- biphenyl) series, Spiro material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenol lithium salt), bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complex, metal complexes of imidazole, thiazole and oxazole, and the like, perylene, and BczVBi (3,3 ') to increase blue light emission efficiency. [(1,1'-biphenyl) -4,4'-diyldi-2,1-ethenediyl] bis (9-ethyl) -9H-carbazole; DSA (distrylamine) can be used by doping in small amounts. In the case of red, DCJTB ([2- (1,1-dimethylethyl) -6- [2- (2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H, 5H Small amounts of doping such as -benzo (ij) quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene] -propanedinitrile) can be used. When forming a light emitting layer using a process such as inkjet printing, roll coating, or spin coating, organic molecules such as polyphenylene vinylene (PPV) -based polymers or polyfluorene (poly fluorene) are organic. It can be used for the light emitting layer.

The electron transport layer is positioned on the organic light emitting layer. The electron transport layer needs a material having high electron injection efficiency from the cathode positioned thereon and capable of efficiently transporting the injected electrons. To this end, it must be made of a material having high electron affinity and electron transfer speed and excellent stability to electrons. Examples of the electron transport material that satisfies such conditions include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The electron injection layer is stacked on the electron transport layer. The electron injection layer is a metal complex compound such as Balq, Alq3, Be (bq) 2, Zn (BTZ) 2, Zn (phq) 2, PBD, spiro-PBD, TPBI, Tf-6P, aromatic compound with imidazole ring, It can be produced using a low molecular weight material containing boron compounds and the like. At this time, the electron injection layer may be formed in a thickness range of 100 ~ 300Å.

The cathode is positioned on the electron injection layer. This cathode serves to inject electrons. As the material used as the cathode, it is possible to use the material used for the anode, and a metal having a low work function is more preferable for efficient electron injection. In particular, a suitable metal such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or a suitable alloy thereof can be used. In addition, an electrode having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum having a thickness of 100 μm or less may also be used.

As described above, a hole injection material, a hole transport material, suitable for fluorescence and phosphorescent devices of all colors, such as red, green, blue, white, etc., according to a compound including two or more five-membered hetero rings described with reference to Chemical Formulas 1 to 12, It can be used as a light emitting material, an electron transporting material and an electron injection material, and can be used as a host material for phosphorescent dopants of various colors.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.

Meanwhile, the present invention includes a display device including the organic electric element described above, and a terminal including a control unit for driving the display device. This terminal means a current or future wired or wireless communication terminal. The terminal according to the present invention described above may be a mobile communication terminal such as a mobile phone, and includes all terminals such as a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, various computers, and the like.

Example

Hereinafter, the present invention will be described in more detail with reference to Preparation Examples and Experimental Examples. However, the following Preparation Examples and Experimental Examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Manufacturing example

Hereinafter, the preparation or synthesis examples of the compounds comprising two or more five-membered hetero rings belonging to the formula (6). However, since the number of compounds including two or more five-membered hetero rings belonging to Formula 6 is large, one or two of the compounds including two or more five-membered hetero rings belonging to Formula 6 will be described. Those skilled in the art, ie, those skilled in the art, may prepare compounds including two or more five-membered heterocycles belonging to the present invention, which are not illustrated by the preparations described below.

Step 1) Synthesis of Intermediate A

Figure 112009076810511-pat00048

4-bromonaphthalen-1-ylboronic acid and (2-bromophenyl) (methyl) sulfane

Add tetrakis (triphenylphophine) palladium (0) and potassium carbonate, add THF (tetrahydrofuran) and water (3: 1) and stir at 70 ℃. After completion of the reaction, the mixture was extracted with CH 2 Cl 2 , washed with water, a small amount of water was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated. The resulting product was recrystallized with CH 2 Cl 2 and hexane solvent The desired intermediate A was obtained (yield: 70%).

Step 2) Synthesis of Intermediate B

Figure 112009076810511-pat00049

The intermediate A obtained in step 1) is dissolved in acetic acid, and hydrogen peroxide dissolved in acetic acid is dropped dropwise and stirred at room temperature for 6 hours. After completion of the reaction, acetic acid was removed using a decompression device and separated using column chromatography to obtain the desired intermediate B (yield: 92%).

Step 3) Synthesis of Intermediate C

Figure 112009076810511-pat00050

Add Intermediate B and trifluoromethanesulfonic acid obtained in step 2), stir at room temperature for 24 hours, and slowly add water and pyridine (8: 1) to reflux for 30 minutes. Lower the temperature, extract with CH 2 Cl 2 and wipe with water. A small amount of water was removed with anhydrous MgSO 4 , filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated using column chromatography to give the desired intermediate C (yield: 80%).

Step 4) Synthesis of Intermediate D

Figure 112009076810511-pat00051

The intermediate C, Pd (PPh 3 ) 4 and K 2 CO 3 obtained in step 3) were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with CH 2 Cl 2 and wiped with water. A small amount of water was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated and the resulting product was separated using column chromatography to give the desired intermediate D (yield: 70%).

Step 5) Synthesis of Intermediate E

Figure 112009076810511-pat00052

Intermediate D and triphenylphosphine obtained in step 4) were dissolved in o -dichlorobenzene and refluxed for 24 hours. At the end of the reaction, the solvent was removed using distillation under reduced pressure, and the concentrated product was separated using column chromatography to give the desired intermediate E (yield: 61%).

Synthesis Example 1 Synthesis of Compound 4

Figure 112009076810511-pat00053

Intermediate E and bromobiphenyl, Pd 2 (dba) 3 , P ( t Bu) 3 and NaO t Bu synthesized in step 5) were dissolved in toluene solvent and stirred at 110 ° C. for 6 hours. I was. After the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removal of a small amount of water with anhydrous MgSO 4 and filtration under reduced pressure, the resulting organic solvent was concentrated to give the desired compound 4 by column chromatography (yield: 65%).

Synthesis Example 2 Synthesis of Compound 56

Figure 112009076810511-pat00054

The intermediate E synthesized in step 5) and 4,4'-dibromobiphenyl, Pd 2 (dba) 3 , P ( t Bu) 3 and NaO t Bu were dissolved in toluene solvent. And stirred at 110 ° C. for 6 hours. After the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated to give the desired compound 56 by column chromatography (yield: 52%).

Synthesis Example 3 Synthesis of Compound 94

Figure 112009076810511-pat00055

Compound 4 and NBS (N-bromosuccinimide) obtained in Synthesis Example 1 were dissolved in CH 2 Cl 2 , and stirred at room temperature for 3 hours. Upon completion of the reaction, an aqueous sodium bicarbonate solution was added, stirred for 30 minutes, and extracted with CH 2 Cl 2 . After removal of water in the reaction with anhydrous MgSO 4 and filtration under reduced pressure, the product obtained by concentration of the organic solvent was separated by column chromatography to give the desired intermediate F (yield: 75%). Thereafter, intermediate F and diphenylamine, Pd 2 (dba) 3 , P ( t Bu) 3 and NaO t Bu were dissolved in toluene solvent, and then stirred at 110 ° C. for 6 hours. After the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removal of a small amount of water with anhydrous MgSO 4 and filtration under reduced pressure, the organic solvent was concentrated to give the desired product 94 by column chromatography (yield: 69%).

Synthesis Example 4 Synthesis of Compound 107

Figure 112009076810511-pat00056

In Synthesis Example 3, intermediate F was dissolved in anhydrous THF, the temperature of the reaction was lowered to 8 ° C., n-BuLi (2.5 M in hexane) was slowly added dropwise, and the reaction was stirred at 0 ° C. for 1 hour. Then, the temperature of the reaction was lowered to 78 ℃, trimethyl borate was added dropwise, and stirred at room temperature for 12 hours. When the reaction was completed, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with ether. After removing the water in the reaction with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired intermediate G (yield: 68%).

Thereafter, intermediate F and diphenylamine, Pd 2 (dba) 3 , P ( t Bu) 3 and NaO t Bu were dissolved in toluene solvent, and then stirred at 110 ° C. for 6 hours. After the reaction, the reaction was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removal of a small amount of water with anhydrous MgSO 4 and filtration under reduced pressure, the organic solvent was concentrated to give the desired compound 107 by column chromatography (yield: 38%).

Manufacturing Evaluation of Organic Field Devices

Compounds 4 , 56 , 94 , and 107 obtained through synthesis were used as light emitting host materials of the light emitting layer, respectively, to fabricate an organic light emitting diode according to a conventional method. First, a copper phthalocyanine (hereinafter abbreviated as CuPc) film was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a thickness of 10 nm.

Subsequently, 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as a-NPD) was vacuum-deposited on the membrane as a major transport compound. A hole transport layer was formed. After the hole transport layer was formed, each of compounds 4 , 56 , 94, or 107 was deposited as a phosphorescent host material on the hole transport layer to form a light emitting layer.

At the same time, tris (2-phenylpyridine) iridium (abbreviated as I r (ppy) 3 hereinafter) was added as a phosphorescent Ir metal complex dopant. At this time, the concentration of I r (ppy) 3 in the light emitting layer was 5% by weight. (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm as a hole blocking layer. Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq 3 ) was formed into an electron injection layer to a thickness of 40 nm. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm to use an Al / LiF as a cathode to prepare an organic light emitting device.

Comparative Experimental Example 1

For comparison, an organic electroluminescent device having the same structure as the test example was manufactured using a compound represented by Formula 7 (hereinafter abbreviated as CBP) as a light emitting host material instead of the compound of the present invention.

Figure 112009076810511-pat00057

Emitting layer
Host material
Voltage
(V)
Current density
(mA / cm 2 )
Luminance
(cd / m 2 )
Luminous efficiency
(cd / A)
Chromaticity coordinates
(x, y)
Example 1 Compound 4 5.8 0.31 107 48.3 (0.30, 0.60) Example 2 Compound 56 5.9 0.33 105 45.2 (0.32, 0.61) Example 3 Compound 94 5.8 0.31 107 48.3 (0.30, 0.60) Example 4 Compound 107 5.8 0.31 107 48.3 (0.30, 0.60) Comparative Example 1 CBP 6.1 0.31 101 32.6 (0.33, 0.61)

As can be seen from the results of Table 1, the organic light emitting device using the organic light emitting device material of the present invention is not only excellent in the luminous efficiency compared to the CBP used as a comparative example, but also obtained a green light emission with significantly improved color purity Therefore, it can be used as a phosphorescent host material of the organic light emitting device can significantly improve the luminous efficiency and color purity.

It is apparent that the same effect can be obtained even when the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, the host material of the light emitting layer, as well as the electron injection layer, the electron transport layer, the hole injection layer and the hole transport layer.

While the present invention has been described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention are not limited by these embodiments.

The protection scope of the present invention should be interpreted by the following claims, and all the technologies within the equivalent scope should be interpreted as being included in the scope of the present invention.

1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.

Claims (15)

  1. A compound represented by the following formula.
    Figure 112011092195406-pat00058
    In the above formula,
    (1) R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are each independently of each other a hydrogen atom, a halogen atom, a cyan No group, thiol group, substituted or unsubstituted C1-C50 alkyl group, substituted or unsubstituted C1-C50 alkoxy group, substituted or unsubstituted C1-C50 alkenyl group, substituted or unsubstituted C5-C5 Substitutes containing at least one aryl group of 60, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) Or a substituted or unsubstituted C 5 to C 5 containing at least one unsubstituted heteroalkyl group having 1 to 50 carbon atoms or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si). A heteroaryl group having 5 to 60 carbon atoms or at least one heteroaryl group containing 60 (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si); Time and, R 1 to R 12 may form a saturated or unsaturated ring bonded to each other adjacent group.
    (2) X is sulfur (S) or oxygen (O).
    (3) Y represents a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, a thiol group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon number 5 To 60 arylene group, substituted or unsubstituted aryl group having 5 to 60 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen (O), phosphorus ( A substituted or unsubstituted heteroalkyl group having at least one of P) and silicon (Si) or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) At least one substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms or at least one containing sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) Or a substituted or unsubstituted heteroaryloxy group having 5 to 60 carbon atoms.
    (4) n is an integer of 1 or 2.
  2. A compound represented by the following formula.
    Figure 112011092195406-pat00059
    In the above formula, X is sulfur (S) or oxygen (O), Y is hydrogen atom, halogen atom, cyano group, alkoxy group, thiol group, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted Alkenyl groups having 1 to 50 carbon atoms, substituted or unsubstituted aryl groups having 5 to 60 carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen (O), Substituted or unsubstituted heteroalkyl group having at least one phosphorus (P) and silicon (Si) or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon ( At least one substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms or at least one of sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) Substituted or unsubstituted heteroaryloxy group having 5 to 60 carbon atoms.
  3. A compound represented by the following formula.
    Figure 112011092195406-pat00060
     In the above formula, X is sulfur (S) or oxygen (O), Y is a substituted or unsubstituted arylene group having 5 to 60 carbon atoms.
  4. A compound represented by the following formula.
    Figure 112011092195406-pat00061
    In the above formula,
    (1) R 13 is a hydrogen atom, a halogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms or sulfur It is a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms containing at least one of (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si).
    (2) Ar 1 and Ar 2 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon number 5 An aryl group having from 60 to 60 or a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms including at least one of sulfur (S), nitrogen (N), oxygen (O), phosphorus (P), and silicon (Si). .
    (3) X is sulfur (S) or oxygen (O).
  5. A compound represented by the following formula.
    Figure 112011092195406-pat00062
    In the above formula,
    (1) R 14 and R 15 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms or sulfur (S), nitrogen Substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms containing at least one (N), oxygen (O), phosphorus (P) and silicon (Si),
    (2) Z independently represents a single bond, or-O-,-S-,-CO-,-SO 2 -,-NR 16 -,-PR 17 -,-SiR 18 R 19- , substituted or unsubstituted An arylene group having 5 to 60 carbon atoms in the ring, wherein R 16 to R 19 are each independently a hydrogen atom, a halogen atom, a cyano group, a thiol group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted group An alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S ), A substituted or unsubstituted heteroalkyl group having 1 to 50 carbon atoms or at least one of nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) or sulfur (S), nitrogen (N), Substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms or at least one of oxygen (O), phosphorus (P) and silicon (Si) or sulfur (S), nitrogen ( N), a substituted or unsubstituted heteroaryloxy group having 5 to 60 carbon atoms containing at least one of oxygen (O), phosphorus (P) and silicon (Si),
    (3) X is sulfur (S) or oxygen (O).
  6. The method of claim 1,
    R 1 to R 12 combine with adjacent groups to form a saturated or unsaturated ring.
  7. The compound according to any one of claims 1 to 5, wherein the compound is
    Figure 112011092195406-pat00063
    Figure 112011092195406-pat00064
    Figure 112011092195406-pat00065
    Figure 112011092195406-pat00066
    Figure 112011092195406-pat00067
    Figure 112011092195406-pat00068
    Figure 112011092195406-pat00069
    Figure 112011092195406-pat00070
    Figure 112011092195406-pat00071
    Figure 112011092195406-pat00072
    Figure 112011092195406-pat00073
    Figure 112011092195406-pat00074
    Figure 112011092195406-pat00075
    Figure 112011092195406-pat00076
    Figure 112011092195406-pat00077
    Figure 112011092195406-pat00078
    Figure 112011092195406-pat00090
    Figure 112011092195406-pat00091
    Figure 112011092195406-pat00092
    Figure 112011092195406-pat00093
    Figure 112011092195406-pat00094
    Figure 112011092195406-pat00095
    Figure 112011092195406-pat00096
    Figure 112011092195406-pat00097
    Figure 112011092195406-pat00098
    Figure 112011092195406-pat00099
    Figure 112011092195406-pat00100
    Figure 112011092195406-pat00101
    Figure 112011092195406-pat00102
    Figure 112011092195406-pat00103
    Compounds, characterized in that one selected from the group consisting of.
  8. An organic electric device comprising at least one organic material layer containing the compound of any one of claims 1 to 5.
  9. 9. The method of claim 8,
    The organic electroluminescent device according to claim 1, wherein the organic layer is formed by a solution process.
  10. 9. The method of claim 8,
    The organic electroluminescent device is an organic electroluminescent device comprising a first electrode, the at least one organic material layer and the second electrode in a stacked form sequentially.
  11. The method of claim 10,
    The organic material layer includes a light emitting layer,
    The organic electroluminescent device according to claim 1, wherein the compound is used as a host material in the emission layer.
  12. An electronic device comprising the organic electric element of claim 8;
    And a control unit for driving the electronic device.
  13. The method of claim 12,
    The organic electroluminescent device includes an organic light emitting diode (OLED), an organic solar cell, an organic photoconductor (OPC) drum, an organic transistor (organic TFT), a photodiode, an organic laser, and a laser diode. Terminal) characterized in that one of.
  14. delete
  15. Compound which is one of the following compounds.
    Figure 112012043273084-pat00112
    Figure 112012043273084-pat00113
    Figure 112012043273084-pat00114
    Figure 112012043273084-pat00115
    Figure 112012043273084-pat00116
    Figure 112012043273084-pat00117
    Figure 112012043273084-pat00118
    Figure 112012043273084-pat00119
    Figure 112012043273084-pat00120
    Figure 112012043273084-pat00121
    Figure 112012043273084-pat00122
KR20090123544A 2009-12-11 2009-12-11 Compound Containing 5-Membered Heterocycle And Organic Electronic Element Using The Same, Terminal Thereof KR101219492B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR20090123544A KR101219492B1 (en) 2009-12-11 2009-12-11 Compound Containing 5-Membered Heterocycle And Organic Electronic Element Using The Same, Terminal Thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR20090123544A KR101219492B1 (en) 2009-12-11 2009-12-11 Compound Containing 5-Membered Heterocycle And Organic Electronic Element Using The Same, Terminal Thereof

Publications (2)

Publication Number Publication Date
KR20110066766A KR20110066766A (en) 2011-06-17
KR101219492B1 true KR101219492B1 (en) 2013-01-28

Family

ID=44399525

Family Applications (1)

Application Number Title Priority Date Filing Date
KR20090123544A KR101219492B1 (en) 2009-12-11 2009-12-11 Compound Containing 5-Membered Heterocycle And Organic Electronic Element Using The Same, Terminal Thereof

Country Status (1)

Country Link
KR (1) KR101219492B1 (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014196580A1 (en) * 2013-06-04 2014-12-11 出光興産株式会社 Nitrogen-containing heterocyclic derivative, organic electroluminescence element material using same, and organic electroluminescence element and electronic device using same
CN105131020A (en) * 2014-05-28 2015-12-09 德山新勒克斯有限公司 Compound for organic electronic element, organic electronic element using the same and an electronic device thereof
US9246111B1 (en) 2014-07-10 2016-01-26 Samsung Display Co., Ltd. Organic light-emitting device
US9401484B2 (en) 2014-07-10 2016-07-26 Samsung Display Co., Ltd. Organic light-emitting device having increased electron transport ability of an electron transport region
CN105810837A (en) * 2015-01-16 2016-07-27 三星显示有限公司 Organic light-emitting device
CN107531718A (en) * 2016-03-16 2018-01-02 德山新勒克斯有限公司 Organic electroluminescence device compound, organic electroluminescence device and its electronic installation using the compound
US9887244B2 (en) 2016-04-06 2018-02-06 Samsung Display Co., Ltd. Organic light-emitting device
US10032999B2 (en) 2016-09-29 2018-07-24 Samsung Sdi Co., Ltd. Compound for organic optoelectric device, composition for organic optoelectric device and organic optoelectric device and display device
US10096784B2 (en) 2016-09-21 2018-10-09 Samsung Sdi Co., Ltd. Compound for organic optoelectric device, composition for organic optoelectric device and organic optoelectric device and display device

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8049411B2 (en) 2008-06-05 2011-11-01 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
KR101477614B1 (en) * 2010-09-17 2014-12-31 롬엔드하스전자재료코리아유한회사 Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN103429570A (en) * 2011-03-24 2013-12-04 出光兴产株式会社 Bis-carbazole derivative and organic electroluminescent element using same
KR101497124B1 (en) * 2011-11-28 2015-03-06 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
KR20130083817A (en) * 2012-01-13 2013-07-23 덕산하이메탈(주) Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof
KR101498278B1 (en) * 2012-01-18 2015-03-06 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US20160276599A1 (en) * 2012-01-18 2016-09-22 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same and electronic device thereof
US9716236B2 (en) * 2012-01-18 2017-07-25 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same and electronic device thereof
JP6339071B2 (en) * 2012-07-23 2018-06-06 メルク パテント ゲーエムベーハー Materials for organic electroluminescent devices
KR20140108022A (en) 2013-02-28 2014-09-05 삼성디스플레이 주식회사 Compound and organic light emitting device comprising the same
KR20140126610A (en) 2013-04-23 2014-10-31 삼성디스플레이 주식회사 Organic light emitting diode
KR101718887B1 (en) * 2013-07-01 2017-04-05 삼성디스플레이 주식회사 Organic light emitting diodes
US9660200B2 (en) 2013-07-01 2017-05-23 Samsung Display Co., Ltd. Organic light-emitting device
JP2016179943A (en) * 2013-07-11 2016-10-13 出光興産株式会社 Compound, and organic electroluminescent element prepared therewith
WO2015037965A1 (en) * 2013-09-16 2015-03-19 Rohm And Haas Electronic Materials Korea Ltd. Novel organic electroluminescent compounds and organic electroluminescent device comprising the same
KR20150064804A (en) 2013-12-03 2015-06-12 삼성디스플레이 주식회사 Compound and organic light emitting device comprising same
KR20150065471A (en) 2013-12-05 2015-06-15 삼성디스플레이 주식회사 Organic light emitting device
JP6181116B2 (en) * 2014-07-24 2017-08-16 ドク サン ネオルクス カンパニー リミテッド Organic electronic device and electronic device including the same
KR101921680B1 (en) * 2014-07-24 2019-02-13 덕산네오룩스 주식회사 An organic electronic element and an electronic device comprising it
US20180029983A1 (en) * 2015-02-16 2018-02-01 Idemitsu Kosan Co., Ltd. Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device
KR20170076474A (en) 2015-12-24 2017-07-04 삼성전자주식회사 Condensed cyclic compound and organic light emitting device including the same
KR20170082377A (en) 2016-01-06 2017-07-14 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof
WO2019171233A1 (en) * 2018-03-09 2019-09-12 株式会社半導体エネルギー研究所 Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080085001A (en) * 2005-12-01 2008-09-22 신닛테츠가가쿠 가부시키가이샤 Compound for organic electroluminescent element and organic electroluminescent element

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080085001A (en) * 2005-12-01 2008-09-22 신닛테츠가가쿠 가부시키가이샤 Compound for organic electroluminescent element and organic electroluminescent element

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014196580A1 (en) * 2013-06-04 2014-12-11 出光興産株式会社 Nitrogen-containing heterocyclic derivative, organic electroluminescence element material using same, and organic electroluminescence element and electronic device using same
US9837615B2 (en) 2013-06-04 2017-12-05 Idemitsu Kosan Co., Ltd. Nitrogen-containing heterocyclic derivative, organic electroluminescence element material using same, and organic electroluminescence element and electronic device using same
CN105131020A (en) * 2014-05-28 2015-12-09 德山新勒克斯有限公司 Compound for organic electronic element, organic electronic element using the same and an electronic device thereof
CN105131020B (en) * 2014-05-28 2018-03-09 德山新勒克斯有限公司 Organic electric element compound, organic electric element and its electronic installation using it
US9401484B2 (en) 2014-07-10 2016-07-26 Samsung Display Co., Ltd. Organic light-emitting device having increased electron transport ability of an electron transport region
US9246111B1 (en) 2014-07-10 2016-01-26 Samsung Display Co., Ltd. Organic light-emitting device
CN105810837A (en) * 2015-01-16 2016-07-27 三星显示有限公司 Organic light-emitting device
CN107531718A (en) * 2016-03-16 2018-01-02 德山新勒克斯有限公司 Organic electroluminescence device compound, organic electroluminescence device and its electronic installation using the compound
US9887244B2 (en) 2016-04-06 2018-02-06 Samsung Display Co., Ltd. Organic light-emitting device
US10096784B2 (en) 2016-09-21 2018-10-09 Samsung Sdi Co., Ltd. Compound for organic optoelectric device, composition for organic optoelectric device and organic optoelectric device and display device
US10032999B2 (en) 2016-09-29 2018-07-24 Samsung Sdi Co., Ltd. Compound for organic optoelectric device, composition for organic optoelectric device and organic optoelectric device and display device

Also Published As

Publication number Publication date
KR20110066766A (en) 2011-06-17

Similar Documents

Publication Publication Date Title
JP5583349B2 (en) Novel anthracene derivative and organic electronic device using the same
KR100867526B1 (en) New diamine derivatives, preparation method thereof and organic electronic device using the same
KR101506999B1 (en) Compound for organic photoelectric device and organic photoelectric device including the same
JP5808857B2 (en) Novel compound and organic electronic device using the same
KR101576326B1 (en) Organic light emitting device material and organic light emitting device using the same
EP2660300B1 (en) Novel compound, and organic light-emitting device using same
JP5497045B2 (en) Novel anthracene derivative and organic electronic device using the same
TWI495635B (en) Hetero-cyclic compound and organic electronic device using the same
EP2750214A2 (en) Organic light-emitting device and method for manufacturing same
EP2514798A2 (en) Compound for organic photoelectric device and organic photoelectric device including same
WO2010131855A2 (en) Compound containing a 5-membered heterocycle and organic light-emitting diode using same, and terminal for same
KR101029082B1 (en) Chemical and organic electronic element using the same, electronic device thereof
KR20130115564A (en) New compound and organic light emitting device using the same
JP2014527021A (en) Compound, organic electric element using the same, and electronic device thereof
KR20100079458A (en) Bis-carbazole chemiclal and organic electroric element using the same, terminal thererof
EP2415773B1 (en) Organic electronic device, compounds for same, and terminal
EP2431445A2 (en) Compound for organic photoelectric device and organic photoelectric device comprising same
JP5891253B2 (en) Organic electroluminescence device
JP5432147B2 (en) Organometallic complex derivative and organic light emitting device using the same
JP5638612B2 (en) Novel heterocyclic derivative and organic light emitting device using the same
US9079920B2 (en) Compound containing 5-membered heterocycles, organic light-emitting device using same, and terminal comprising the latter
KR101775188B1 (en) Fluoranthene compound and organic electronic device comprising the same
KR101072817B1 (en) Chemical and organic electronic element using the same, electronic device thereof
KR20110066763A (en) Compound containing indoloacridine and organic electronic element using the same, terminal thereof
KR101219492B1 (en) Compound Containing 5-Membered Heterocycle And Organic Electronic Element Using The Same, Terminal Thereof

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E90F Notification of reason for final refusal
E701 Decision to grant or registration of patent right
N231 Notification of change of applicant
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20151228

Year of fee payment: 4

FPAY Annual fee payment

Payment date: 20161221

Year of fee payment: 5

FPAY Annual fee payment

Payment date: 20181205

Year of fee payment: 7