KR101789672B1 - New organic light emitting compound having highly solubility, and process for the preparation organic electroluminescent device comprising the same compound - Google Patents
New organic light emitting compound having highly solubility, and process for the preparation organic electroluminescent device comprising the same compound Download PDFInfo
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Abstract
The present invention relates to a novel organic light emitting compound and an organic light emitting device including the same. More particularly, the present invention relates to a compound capable of hydrogen bonding at the terminal of a carbazole-based compound comprising carbazole Which is capable of forming a stable organic thin film by inducing hydrogen bonding in a functional period including the pyrimidine ring at a predetermined temperature condition and having a functional group containing a pyrimidine ring having a pyrimidine ring, The present invention provides a method for manufacturing an organic light emitting diode having a multi-layer structure by a solution process including the organic light emitting compound according to the present invention.
Description
The present invention relates to a novel organic light emitting compound and an organic light emitting device comprising the same. More particularly, the present invention relates to a novel organic light emitting compound having a functional group containing a pyrimidine ring, which is capable of hydrogen bonding to a carbazole compound having a phosphorescent property And a method for manufacturing an organic light emitting device including the organic light emitting compound.
In organic photoelectric devices, which are attracting attention as a next generation display device, an organic light emitting layer is formed between a substrate coated with a transparent anode material such as ITO and a cathode. When a predetermined voltage is applied to the electrode, holes and holes And the injected electrons combine in the organic light emitting layer to emit light. The organic photoelectric device has a multilayer structure including an organic light emitting layer in addition to a charge blocking layer depending on characteristics of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and a light emitting layer in order to realize an industrially applicable performance .
Each of the layers constituting the organic photoelectric device is mostly formed by vacuum deposition. When a device is manufactured by a vacuum deposition method, it is difficult to increase the area of the device due to the nature of the process, and it is difficult to reduce the manufacturing cost by requiring expensive deposition equipment There is a problem.
To solve these problems, organic optoelectronic devices have been actively studied through a solution process. Since the organic device material used in the conventional vapor deposition method has low solubility in solvents, the solution process usually involves applying a solution comprising a polymer organic material and a solvent and curing the solution. In order to prevent the solution from dissolving the lower layer portion It is necessary to select an appropriate solvent, and in some cases, it is troublesome in a process in which a separate insolubilization treatment is required. In addition, polymeric materials have a disadvantage in that they can be subjected to a solution process and have excellent thin film formation characteristics, but are difficult to produce a high-purity organic photoelectric device due to a molecular weight distribution and have a lower performance than an organic photoelectric device using a low molecular weight compound.
Korean Patent Laid-Open Publication No. 2014-0083412 (the name of the invention: a red phosphorescent host material and an organic electroluminescent device using the same, hereinafter referred to as "Prior Art 1") is substituted with a heteroaromatic, heteroaliphatic, Discloses a technique for a red phosphorescent material that is a benzocarbazole derivative and discloses a method for manufacturing an organic light emitting device including such a red phosphorescent material through a solution process.
Prior Art 1 discloses a technique for forming a light emitting layer using a solution prepared by including a red phosphor, which is a benzocarbazole derivative that can be substituted with heteroaromatic, heteroalicyclic, and aliphatic groups. However, since organic compound compounds such as the conventional art 1 have insufficient solubility in various solvents, there is a problem that it is difficult to uniformly coat the organic thin film when the organic thin film is formed by a solution process. When a multi-layered organic thin film is formed by a solution process, it is necessary to stably cure the lower layer material so that the material of the lower layer is not dissolved by the solution applied to the upper layer. The compound according to the prior art 1 does not have a property to be cured The organic thin film can be deformed by heat.
SUMMARY OF THE INVENTION Accordingly, it is an object of the present invention to provide a novel organic compound having excellent solubility in a solvent and a thin film forming property while improving the performance of an organic device, To provide an organic light emitting compound.
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are not intended to limit the invention to the precise form disclosed. There will be.
According to an aspect of the present invention, there is provided an organic electroluminescent compound comprising at least one functional group containing a pyrimidine ring at the terminal of a carbazole-based compound comprising carbazole, wherein the pyrimidine ring Is capable of hydrogen bonding. ≪ Desc /
Further, in one embodiment of the present invention, the carbazole-based compound may be selected from the compounds represented by the following general formulas (1a) to (1f), and the functional group containing a pyrimidine ring capable of hydrogen bonding to the benzene ring of the carbazole- Or more.
Also, an embodiment of the present invention provides an organic luminescent compound having two or more functional groups including a pyrimidine ring having hydrogen-binding characteristics, wherein the organic luminescent compound having at least two pyrimidine rings And forming an organic thin film by hydrogen bonding in a functional period including the pyrimidine ring.
In one embodiment of the present invention, an organic light emitting compound having at least two functional groups including a pyrimidine ring may be a compound represented by the following formula (2).
(2)
(In the
The functional group containing the pyrimidine ring according to the present invention is selected from a furan functional group and a pyrimidine functional group. In one embodiment, the functional group having a pyrimidine functional group is formed from a compound represented by the following general formula (3a) or And the like.
(Wherein R6 to R11 in the formulas (3a) and (3b) may be the same or different from each other and each independently represents H, D, F, Cl, Br, I, amino group, straight chain alkyl having 1 to 12 carbon atoms, An acid, an alcohol having 1 to 10 carbon atoms, and a halogenated alkyl having 1 to 10 carbon atoms.
In one embodiment of the present invention, the purine functional group may be a functional group formed from a compound selected from the following formulas (3c) to (3h).
Wherein
According to an aspect of the present invention, there is provided a method for forming an organic thin film layer including an organic light emitting compound having at least two functional groups including a pyrimidine ring. In one embodiment of the present invention, a method for producing an organic thin film layer comprises the steps of i) dissolving an organic luminescent compound in a solvent to prepare a solution, ii) preparing a substrate, iii) And iv) heat treating the substrate coated with the solution for a predetermined period of time to form a thin film.
In one embodiment of the present invention, the solvent is 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, 1,2,4-trichlorobenzene, , 1,3,5-Trichlorobenzene, chloroform, tetrahydrofuran, and ethanol. The mixing time may be one or two or more.
Further, in another embodiment of the present invention, the method may further include the step of adding a light emitting dopant between the step i) and the step ii), and further an organic light emitting layer may be formed by further including a light emitting dopant.
Further, in one embodiment of the present invention, the method of applying a solution may be performed by various methods such as spin coating, gravure offset printing, reverse offset printing, screen printing, roll to roll printing, slot die coating, dip coating, spray coating, And heating the substrate coated with the solution to a temperature of 70 to 170 ° C to induce hydrogen bonding between the functional groups including the pyrimidine ring to form an organic thin film layer .
According to an aspect of the present invention, there is provided an organic electroluminescent device comprising an organic electroluminescent compound having at least one functional group containing a pyrimidine ring, , And organic solar cells.
(Ii) forming an anode on the substrate; (iii) forming a hole injecting layer on the anode; (iv) forming a hole transporting layer on the hole injecting layer; (Vi) forming a light emitting layer on top of the hole transport layer, (vi) forming an electron transporting layer on the light emitting layer, and (vii) forming a cathode on the electron transporting layer, wherein the light emitting layer There is provided a method of manufacturing an organic light emitting device including an organic light emitting compound having at least two functional groups including a pyrimidine ring according to an embodiment of the present invention.
According to the embodiment of the present invention, the solubility of a low-molecular organic compound having low solubility can be improved by providing a functional group containing a pyrimidine ring at the end of a carbazole-based compound having hole transporting and phosphorescence properties, When the compound has two or more functional groups including a pyrimidine ring, it is possible to form a stable organic thin film by hydrogen bonding between functional groups including a pyrimidine ring. A third effect that a stable multi-layered device can be fabricated without the phenomenon that adjacent layers are dissolved by a solution even if an organic thin film layer of a multi-layer structure is formed through a solution process, and the organic EL device can be made large- Has a fourth effect.
The organic luminescent compound according to the present invention has a functional group containing a pyrimidine ring which is capable of hydrogen bonding, so that solubility in various solvents can be improved. In addition, in the prior art, due to the problem of low solubility, the organic thin film is formed through a deposition process. However, the organic luminescent compound according to the present invention can provide properties suitable for various solution processes by improving solubility .
Further, in the prior art, even if an organic thin film is formed through a solution process, there has been a problem in that it must be performed under a high temperature condition in order to form a stable organic thin film. However, since the organic luminescent compound according to the present invention is excellent in solubility in a solvent and can form a thin film that is stable to heat even in a low-temperature process due to hydrogen bonding during the functional period of the compound, mass production of organic devices, And the cost can be reduced.
It should be understood that the effects of the present invention are not limited to the above effects and include all effects that can be deduced from the detailed description of the present invention or the configuration of the invention described in the claims.
1 is a cross-sectional schematic diagram of an organic light emitting diode according to an embodiment of the present invention.
2 is a graph showing UV-vis spectra and PL spectra of organic electroluminescent compound (MCP-pym) and organic electroluminescent compound (MCP) according to one embodiment of the present invention.
3 is a graph showing the EL spectrum of the organic light emitting device and the PL spectrum of the blue phosphorescent dopant (Fir6) according to an embodiment of the present invention.
4 is a graph showing current efficiency according to a change in current density of an organic light emitting diode manufactured according to an embodiment of the present invention.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described with reference to the accompanying drawings. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth 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 the specification, when a part is referred to as being "connected" (connected, connected, coupled) with another part, it is not only the case where it is "directly connected" "Is included. Also, when an element is referred to as "comprising ", it means that it can include other elements, not excluding other elements unless specifically stated otherwise.
The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The singular expressions include plural expressions unless the context clearly dictates otherwise. In this specification, the terms "comprises" or "having" and the like refer to the presence of stated features, integers, steps, operations, elements, components, or combinations thereof, But do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.
In the present invention, " carbazole " is a known compound, which means a compound in which two benzene rings are bonded to both sides of a nitrogen-containing heterocycle, and includes all substituted or unsubstituted structures thereof. Further, in the present invention, the carbazole-based compound means a compound comprising a substituted or unsubstituted carbazole. In the present invention, the pyrimidine ring means a heterocyclic ring composed of four carbon atoms and two nitrogen atoms, and includes all substituted or unsubstituted pyrimidine rings. In the present invention, the purine functional group means a compound containing a substituted or unsubstituted purine molecule, and the purine molecule means an aromatic ring compound having a structure in which a pyrimidine ring and an imidazole ring share one carbon-carbon bond do.
Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings and formulas.
The organic luminescent compound according to the present invention has at least one functional group containing a pyrimidine ring at the terminal of the carbazole compound, and the functional group containing a pyrimidine ring can be hydrogen-bonded. Preferably, the carbazole-based compound is selected from the carbazole-based compounds represented by the following general formulas (1a) to (1f), and the benzazole ring of the carbazole-based compound may have at least one functional group containing a pyrimidine ring.
The organic luminescent compound according to the present invention has a functional group containing a pyrimidine ring capable of hydrogen bonding to a carbazole compound which is excellent in hole transporting property and is large in triplet band gap and is used as a phosphorescent host material, The solubility in various solvents as well as the properties can be ensured and the solution process can be performed. In addition, it is preferable that the organic luminescent compound does not include, but is not limited to, a carbazole-based compound in which a substituent such as an alkyl group is not bonded except for a functional group containing a pyrimidine ring. However, in the case of not having a substituent such as an alkyl group, the synthesis of the compound is simpler and the formation of the organic thin film is easy.
In the present invention, the functional group containing a pyrimidine ring may be selected from a pyrimidine functional group and a purine functional group. In one embodiment of the present invention, the pyrimidine functional group is a compound represented by the following formula As shown in FIG.
(Wherein R6 to R11 in the formulas (3a) and (3b) may be the same or different from each other and each independently represents H, D, F, Cl, Br, I, amino group, straight chain alkyl having 1 to 12 carbon atoms, An acid, an alcohol having 1 to 10 carbon atoms, and a halogenated alkyl having 1 to 10 carbon atoms.
More preferably, the pyrimidine functional group formed from the compound represented by the general formula (3a) may be selected from a plurality of substance groups represented by the following formulas, but is not limited thereto.
(* In the above formula represents the bonding of the organic light emitting compound to the benzene ring.)
In addition, the pyrimidine functional group formed from the compound represented by the formula (3b) may be selected from a plurality of substance groups represented by the following formulas, but it is not limited thereto.
(* In the above formula represents the bonding of the organic light emitting compound to the benzene ring.)
Further, in one embodiment of the present invention, the purine functional group may be formed from a compound selected from the following formulas (3c) to (3h).
Wherein
Preferably, the purine functional groups may be selected from a number of groups of materials represented by the following formulas, but are not limited thereto.
(* In the above formula represents the bonding of the organic light emitting compound to the benzene ring.)
In addition, the organic luminescent compound according to the present invention may preferably have at least two functional groups including a pyrimidine ring. The organic luminescent compound according to the present invention can improve solubility by providing a functional group containing a pyrimidine ring at the terminal of a carbazole compound in which solution process is difficult due to its low solubility in a solvent, and further, a function including a pyrimidine ring An organic light emitting compound having two or more groups can form an organic thin film by hydrogen bonding between functional groups including a pyrimidine ring. Specifically, the functional group containing the pyrimidine ring according to the present invention contains a bond capable of hydrogen bonding such as an amide group and a carbonyl group in the compound. Accordingly, when two or more functional groups including a pyrimidine ring are included in the compound for an organic device, the organic thin film can be formed by inducing the bonding in the above-described functional sintering function period.
In one embodiment of the present invention, the organic light emitting compound having two or more functional groups including a pyrimidine ring may be a compound represented by the following formula (2), but it is not limited thereto.
(2)
(In the
In addition, the organic light emitting compound according to the present invention can be characterized in that the hardness of the thin film can be controlled according to the number of functional groups including the pyrimidine ring provided at the terminal. The organic luminescent compound according to the present invention forms a network structure through a hydrogen bond between functional groups including a pyrimidine ring provided at a terminal. When the number of functional groups including a pyrimidine ring provided in an organic luminescent compound increases , A thin film having a more dense structure can be formed by hydrogen bonding.
Hereinafter, a method for forming an organic thin film layer including an organic light emitting compound having two or more functional groups including a pyrimidine ring according to the present invention will be described.
In one embodiment of the present invention, the organic thin film layer includes a first step of preparing a solution by dissolving the organic luminescent compound in a solvent, a second step of preparing a substrate for coating the solution, A third step of applying a solution, and a step of heat treating the substrate to which the solution has been applied for a predetermined period of time to form a thin film.
The organic luminescent compound according to the present invention may be characterized in that it has a solubility improved by having a functional group containing a pyrimidine ring and is soluble in the solvent of the first step at room temperature. The solvent may be one or more selected from 1,2,3-Trichlorobenzene, 1,2,4-Trichlorobenzene, 1,3,5-Trichlorobenzene, chloroform, tetrahydrofuran, But is not limited to, the following. However, by using a trichlorobenzene-based solvent, the organic luminescent compound according to the present invention is more uniformly dissolved at room temperature, and a side reaction is not caused during heating, so that an organic thin film of high purity can be formed.
In still another embodiment of the present invention, a solution may be prepared by further adding a luminescent dopant between the first step and the second step. The organic electroluminescent compound according to the present invention includes a carbazole compound having hole transporting property and phosphorescence property as described above, and thus can be applied as a host material for a light emitting layer. Therefore, a solution for the light emitting layer can be prepared by further adding a luminescent dopant to the solution of the first step at a predetermined ratio. At this time, the luminescent dopant may be added in an amount of 1 to 10 wt%, more preferably 5 to 10 wt%, based on 100 wt% of the total solution. This will be described in detail in a manufacturing method of an organic light emitting device to be described later.
In the third step of the present invention, the solution is selected from the group consisting of spin coating, gravure offset printing, reverse offset printing, screen printing, roll-to-roll printing, slot die coating, dip coating, spray coating, doctor blade coating, But is not limited to, any one of the following methods.
In the fourth step of the present invention, the step of heat-treating the substrate to which the solution has been applied may be performed at a temperature of 70 to 170 ° C, and the organic light emitting compound according to the present invention may include a pyrimidine ring Can be cured by hydrogen bonding during the functional period to form a thin film. If the temperature is less than 70 ° C, the curing temperature is insufficient and it may be difficult to form a thermally stable organic thin film, which may result in a long process time. When the heat treatment temperature is higher than 170 ° C, the temperature is limited to the above temperature, but the present invention is not limited to this temperature because the stability of the substrate and the compound can not be ensured due to excessive heat.
Hereinafter, a method for manufacturing an organic light emitting device including an organic light emitting compound according to the present invention will be described. FIG. 1 is a cross-sectional view of an organic light emitting device manufactured according to a preferred embodiment of the present invention.
In one embodiment of the present invention, the organic light emitting device includes i) preparing a positive electrode substrate, ii) forming a positive hole injection layer on the positive electrode substrate, iii) forming a positive hole transport layer on the positive hole injection layer, iv) forming a light emitting layer on top of the hole transport layer, v) forming a hole blocking layer on top of the light emitting layer, vi) forming an electron transport layer on top of the hole blocking layer, vi) Forming an injection layer, and vii) forming a cathode on top of the electron injection layer. Hereinafter, a method of manufacturing an organic light emitting device according to the present invention will be described in detail in each of the manufacturing steps in the above-described manner.
In the present invention, the anode substrate may be any substrate coated with a cathode material known in the art. Preferably, the anode substrate may be a substrate coated with a transparent electrode material such as indium-tin-oxide (ITO), fluorine-tin-oxide (FTO), or indium-zinc-oxide (IZO) no.
The next step is to form a Hole Injection Layer (HIL) on the anode substrate. The hole injection layer is formed by including a compound that lowers an injection energy barrier of holes injected from an anode to facilitate hole injection. Examples of such materials include 4,4 ', 4 "-tris (N, N-diphenylamino ) triphenylamine (NATA), 4,4 ', 4 "-Tris (N-3-methylphenyl-N-phenylamino) triphenylamine (m-MTDATA), and poly (3,4-ethylenedioxythiophene) Sulfonic acid) (PEDOT: PSS) are known, and any known material for the hole injection layer can be used without limitation. Preferably, the hole injection layer can be formed by spin coating a PEDOT: PSS solution.
The next step is a step of forming a hole transport layer (HTL) on the upper part of the hole injection layer. The hole transport layer includes a compound which plays a role of transporting holes injected from the anode to the light emitting layer . For example, the hole-transporting layer may include NPB (N, N'-bis (1-naphthyl) -N, N'- diphenyl- (TPD), bis (N- (1-naphthyl-N-phenyl) benzidine), CBP (4,4- N, N'-dicarbazole-biphenyl). It is noted that the hole-injection layer is usually formed by vacuum evaporation of the compound for the hole-injection layer described above, In order to solve such a problem, it is possible to form a hole transporting layer using a hole transporting material having characteristics suitable for a solution process. In an embodiment of the present invention, The hole transporting material may be a compound having two or more functional groups including a pyrimidine ring in a terminal benzene ring of a known triphenylamine compound, The compound represented by the general formula (5-1) may have two or more functional groups including a pyrimidine ring which provides the same effect as the organic light emitting compound according to the present invention, .
[Formula 5-1]
(In the formula 5-1, R 1 to
The next step is to form an emission layer (EML) on top of the hole transport layer. The light emitting layer may be formed by including a light emitting compound alone, or may be formed by mixing a light emitting dopant with a host material having charge transporting properties. In the case of forming a light emitting layer including a light emitting compound alone, it is difficult to fabricate an organic light emitting device having high efficiency because of its excellent light emitting property but low charge transport ability. Therefore, a method of adding a light emitting dopant to a host material having excellent charge transport ability It may be preferable to form the light emitting layer.
The present invention is characterized by using a carbazole-based compound having two or more functional groups including a pyrimidine ring as a host material. Generally, carbazole-based compounds are known to be suitable as host materials because they have excellent charge transporting properties, are thermally stable, and have high triplet energy. In addition, the carbazole-based compound of the present invention has a functional group containing a pyrimidine ring capable of hydrogen bonding at the terminal thereof, thereby improving the solubility and enabling the solution process. The hydrogenation of the functional group containing the pyrimidine ring It has an advantage that a thin film can be easily formed through bonding.
In addition, the luminescent dopant can be selected from phosphorescent luminescent or fluorescent luminescent compounds. Unlike fluorescent luminescence, which emits light when a singlet exciton transitions to a ground state, phosphorescent luminescence is generated by intersystem crossing, It is preferable to use a compound having a phosphorescent luminescent property as a luminescent dopant since the lifetime of the triplet exciton is longer than the luminescent luminescence and the efficiency is higher than that of the fluorescent luminescence. Further, when selecting the host material and the dopant material for forming the light emitting layer, these triplet energy levels should be considered. When the triplet of the host material has a higher energy level than the triplet of the dopant, the energy transfer from the host to the dopant is more stable and the efficiency of the device can be improved. If the triplet energy of the host is lower than the triplet energy of the dopant, energy loss occurs due to endothermic energy transfer, which causes a decrease in luminous efficiency of the device. On the other hand, if the triplet energy level of the host is higher than the triplet energy of the dopant, the luminescence due to the exothermic energy transition can be realized, thereby achieving high luminescence efficiency.
Considering such characteristics, the dopant suitable for the host material according to the present invention may be a blue phosphorescent dopant, specifically (3,5-difluoro-2- (2-pyridyl) phenyl- (2- carboxypyridyl) iridium A dopant selected from the group consisting of FirPic III and Bis (2,4-difluorophenylpyridinato) -tetrakis (1-pyrazolyl) borate iridium III (Fir6) may be used. Methyl-6- (pyrrolidin-4-yl-vinyl) -4H-pyran), dicyclopentadiene (1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran), dicyanomethylene-2-tertiarybutyl-6- , 7,7-tetramethyljulolidyl-9-enyl) -4H-pyran) and dicyanomethylene-2-isopropyl-6- (1,1,7,7-tetramethyljulolidyl- ) -4H-pyran) and the like can be used as a dopant.
In an embodiment of the present invention, a mixed solution is prepared by mixing an organic luminescent compound having two or more functional groups including a pyrimidine ring as a host material and a solvent, and 100 parts by weight of the mixed solution is mixed with a luminescent dopant To 1 wt% to 10 wt% of the solution.
The next step is to form a hole blocking layer (HBL) on the upper portion of the light emitting layer. In one embodiment of the present invention, the hole blocking layer is formed of a material selected from the group consisting of Balq, 2,2 ', 2 "- (1,3,5- benzinetriyl-tris (1-phenyl-1-H-benzimidazole) (TPBi) and 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP).
The next step is to form an electron transport layer (ETL) on the hole blocking layer. The electron transport layer transports electrons injected from the cathode to the light emitting layer, thereby improving the probability of bonding of holes and electrons in the light emitting layer. In order to perform this role, it is preferable to use a substance having excellent electron affinity and good interfacial adhesion with the cathode. In one embodiment of the present invention, the electron transport layer is made of Alq3 (Tris (8-hydroxy-quinolinato) aluminum), Balq (Bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum, BeBq2 hydroxybenzo [h] quinolinato) beryllium). < / RTI >
The next step is to form an electron injection layer (EIL) on the electron transport layer. In an embodiment of the present invention, the electron injecting layer is made of LiF, 8-hydroxyquinolinolato-lithium (Liq), 1, And at least one material selected from the group consisting of 3,5-tri [(3-pyridyl) -phen-3-yl] benzene (TmPyPB).
The next step is to form a cathode on the electron injection layer. The negative electrode material may be formed by depositing a material having a low work function value such as lithium (Li), magnesium (Mg), calcium (Ca), aluminum (Al), Al: Li, Ba: Li or Ca: Li .
When the organic light emitting device is manufactured, it is necessary to design the organic light emitting device so as to maximize the efficiency of the device in consideration of the energy level of the compounds forming each layer. Hereinafter, preferred embodiments and experimental examples of the organic light emitting device including the organic light emitting compound having the functional group including the pyrimidine ring according to an embodiment of the present invention will be described, but the present invention is not limited thereto.
In addition, the organic light emitting compound having a functional group including a pyrimidine ring according to the present invention and the organic thin film layer formed therefrom can be applied to various organic devices other than the organic light emitting device, Photoconductors (OPCs), photodiodes, organic lasers, and organic image sensors.
Hereinafter, examples and experimental examples of the present invention will be described.
[Example 1]
≪ Preparation of a compound represented by the general formula (4) (hereinafter referred to as MCP-pym)
1. Preparation of intermediate A
0.2 g of sodium hydride (NaH) and 50 ml of DMSO were added to the flask, and the mixture was stirred for one hour while maintaining nitrogen atmosphere. Next, a solution prepared by dissolving 1.25 g of 3-bromo-1-propanol and 1.1 g of uracil in 50 ml of DMSO was slowly added to the reaction flask, and 48 Lt; / RTI > for 1 hour. After completion of the reaction, the reaction solution was applied, and the solvent was removed using a vacuum filtration apparatus. The product remaining in the filtration apparatus was washed with a solvent mixture of ethyl acetate and hexane in a volume ratio of 1: 4, and then, intermediate A was obtained. (See Scheme 1 below).
[Reaction Scheme 1]
2. Preparation of intermediate B
0.8 g of potassium phosphate (KH 2 PO 4 ), 0.5 g of intermediate A and 80 ml of DMSO were added to the flask, and the mixture was stirred for one hour while maintaining the atmosphere in a nitrogen atmosphere. Next, 0.72 g of 2-bromo-9H-carbazole was dissolved in 30 ml of DMSO, followed by addition to the potassium phosphate solution, followed by reaction at room temperature for 72 hours with stirring. After completion of the reaction, the precipitate was filtered using a filtration apparatus, and the filtrate was taken to remove the solvent under reduced pressure. The crude product remaining in the filtration apparatus was purified by column chromatography using a mixed solvent of methylene chloride and hexane in a volume ratio of 1:10 to prepare intermediate B. (See
[Reaction Scheme 2]
3. Preparation of a compound represented by the formula (4) (hereinafter referred to as MCP-pym)
1 g of 1,3-dibromobenzene, 2.9 g of Intermediate B, 0.0085 g of copper iodide (CuI), 2.2 g of potassium phosphate (KH 2 PO 4 ), 1 , 2 -trans- 0.48 mL of 1,2-trans-cyclohexane diamine, C 6 H 10 (NH 2 ) 2 ) and 100 mL of 1,4-dioxane were mixed and stirred. The mixture was allowed to react at 50 < 0 > C with stirring for 48 hours. After the reaction was completed, the distilled water layer was removed by using methylene chloride and distilled water, and the organic solvent (methylene chloride) layer was collected. The organic solvent layer was filtered under reduced pressure to remove all of the solvent. The crude product remaining in the filtration apparatus was purified by column chromatography using a mixed solvent of methylene chloride and hexane mixed at a volume ratio of 1: 4 to obtain the final product MCP-pym. (See
[Reaction Scheme 3]
≪ Preparation of a compound represented by the general formula (5) (hereinafter referred to as TPD-pym)
1. Preparation of intermediate C
5 g of N, N'-dim-tolylbiphenyl-4,4'-diamine and 60 ml of chloroform (CHCl 3 ) were added to the flask, and the mixture was stirred for 30 minutes while maintaining nitrogen atmosphere. Next, 15 g of N-bromosuccinimide (C 4 H 4 BrNO 2 ) was slowly added to the reaction solution, and the reaction was allowed to proceed at 70 ° C. for 24 hours. After completion of the reaction, work-up was performed using methylene chloride and distilled water to remove the distilled water layer, and the organic solvent (methylene chloride) layer was collected. The organic solvent layer was filtered under reduced pressure to remove all of the solvent. The crude product remaining in the filtration apparatus was purified by column chromatography using a mixed solvent of methylene chloride and hexane in a volume ratio of 1: 5 to prepare intermediate C. (See
[Reaction Scheme 4]
2. Preparation of intermediate A
Intermediate A was prepared under the same conditions and procedures as above.
3. Preparation of a compound represented by the formula (5) (hereinafter referred to as TPD-pym)
0.8 g of potassium phosphate (KH 2 PO 4 ), 0.5 g of Intermediate A and 80 ml of DMSO were added to the flask and stirred for one hour. Next, 0.8 g of Intermediate C was dissolved in 30 ml of DMSO, added to the reaction flask, and reacted with stirring at room temperature for 72 hours. After completion of the reaction, the precipitate was filtered using a filtration apparatus, the filtrate was collected and the solvent was removed under reduced pressure, and the crude product was purified by column chromatography using a mixed solution obtained by mixing ethyl acetate and hexane in a volume ratio of 1:10 And purified by chromatography to obtain the compound (TPD-pym) represented by the formula (5). (See Scheme 5 below for this).
[Reaction Scheme 5]
An ITO glass substrate was used as the anode substrate, and the ITO substrate was ultrasonically washed with acetone, isopropyl alcohol and distilled water for 30 minutes, and dried to remove impurities.
PEDOT: PSS (PH4083, Celvios) was coated on the ITO coated surface by spin coating and dried at 120 ° C for 30 minutes to form a hole injection layer.
Next, TPD-pym was dissolved in trichlorobenzene to prepare a 30 wt% solution, which was then coated by spin coating and dried at 100 ° C to form a hole transport layer.
Next, the host material MCP-pym was dissolved in chlorobenzene, and a solution for the light emitting layer prepared by adding 9 wt% of Fir6, which is a blue phosphorescent dopant, was applied to the top of the hole transport layer by spin coating, And dried to form a light emitting layer.
Next, TPBi was vacuum-deposited on the luminescent layer under the conditions of a vacuum degree of 1 × 10 -7 Pa and a deposition rate of 2 nm / s to form a hole blocking layer.
Subsequently, Alq3 (Tris- (8-hydroxyquinoline) aluminum) was vapor-deposited under the same deposition conditions to form an electron transport layer, and LiF was vapor-deposited on the electron transport layer to form an electron injection layer. And a negative electrode was formed.
Finally, the organic light emitting device was fabricated with the structure of ITO / PH4083 / TPD-pym / MCP-pym + Fir6 (9 wt%) / TPBi / Alq3 / LiF / Al.
[Comparative Example 1]
(N, N'-bis (1-naphthyl) -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine) as a hole transport material is vacuum deposited to form a hole transport layer, Except that a light emitting layer was formed by vacuum depositing a solution for a light emitting layer prepared by adding 9 wt% of MCP as a dopant and Fir6 as a dopant.
[Experimental Example 1]
≪ 1 > H NMR analysis was performed to confirm the synthesis of the compounds MCP-pym and TPD-pym prepared according to Example 1. NMR analysis of the compound was carried out by dissolving the analyte in deuterochloroform (CDCl 3 ), and the results of the analysis are as follows.
compound MCP - pym Analysis
; 1 H NMR (CDCl 3 , 300 MHz); (m, -CH-), 6.99 (d, -CH-), 5.83 (s, -CH-), 7.69 -H), 2.25 ~ 2.05 (s, -CH2-), 1.53 (s, -CH2-)
compound TPD - pym Analysis
; 1 H NMR (CDCl 3 , 300 MHz); (m, -CH-), 7.63 (t, -CH-), 7.52-7.38 (m, -CH-) (M, -CH3-), 1.98 (m, -CH3-), 7.03 (m, -CH-), 5.38
The abbreviations used in the above 1 H NMR analysis results respectively mean: s: singlet, d: doublet, t: triplet, g: quartet, m: polyline.
[Experimental Example 2]
UV spectra and PL (photoluminescence) spectra were measured to evaluate the optical properties of the compound MCP-pym prepared according to Example 1. UV spectra were measured by dissolving MCP-pym in chloroform and PL spectra were determined by dissolving MCP-pym in chloroform. The results are shown in Fig.
Referring to FIG. 2, it can be seen that the compound MCP-pym prepared by coupling a functional group containing a pyrimidine ring to MCP has almost the same optical properties as the MCP according to the prior art. Accordingly, it can be judged that the organic luminescent compound according to the present invention affects only solubility and thin film formation characteristics without inhibiting the optical properties of MCP.
[Experimental Example 3]
The current density, the current efficiency and the electroluminescence (EL) intensity of the organic light emitting device were measured in order to evaluate the electro-optical characteristics of the organic light emitting device manufactured according to Example 1. FIG. 3 shows the EL spectrum of the organic light emitting device manufactured according to Example 1 and the PL spectrum of
Referring to FIG. 3, it can be seen that the organic light emitting device according to an embodiment of the present invention exhibits a maximum peak at about 460 nm and exhibits a blue emission spectrum characteristic. In addition, the emission spectrum characteristics of the organic light emitting device according to the present invention are almost overlapped with the emission spectrum of FiR6, which is a blue phosphorescent dopant shown in FIG. As a result, it can be seen that when the organic luminescent compound according to the present invention is used as a host material, energy transfer is effectively performed by the dopant material.
4, the maximum current efficiency of the organic light emitting diode according to an embodiment of the present invention is 14 cd / A, which is about 2.5 times higher than that of the device of Comparative Example 1 manufactured through the vapor deposition process Value. Accordingly, when the organic luminescent compound according to the present invention is applied to an organic luminescent device, a solution process can be performed, and a stable multi-layered organic luminescent device can be fabricated without dissolving adjacent layers through a solution process.
It will be understood by those skilled in the art that the foregoing description of the present invention is for illustrative purposes only and that those of ordinary skill in the art can readily understand that various changes and modifications may be made without departing from the spirit or essential characteristics of the present invention. will be. 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, and all changes or modifications derived from the meaning and scope of the claims and their equivalents should be construed as being included within the scope of the present invention.
Claims (20)
A carbazole-based compound comprising at least two functional groups including a pyrimidine ring at the end of the carbazole-based compound, wherein the functional group containing the pyrimidine ring is capable of hydrogen bonding,
The organic luminescent compound having at least two functional groups including the pyrimidine ring is characterized by forming an organic thin film by hydrogen bonding during the functional period including the pyrimidine ring,
Wherein the organic luminescent compound having at least two functional groups including the pyrimidine ring is a compound represented by the following formula 2:
(2)
(Wherein R 1 to R 5 may be the same or different from each other, and at least two of R 1 to R 5 are functional groups containing a pyrimidine ring, and the remainder are hydrogen).
Wherein the functional group containing the pyrimidine ring is selected from a purine functional group and a pyrimidine functional group.
Wherein the pyrimidine functional group is formed from a compound represented by the following formula (3a) or (3b).
(Wherein R6 to R11 in the formulas (3a) and (3b) may be the same or different from each other and each independently represents H, D, F, Cl, Br, I, amino group, straight chain alkyl having 1 to 12 carbon atoms, An acid, an alcohol having 1 to 10 carbon atoms, and a halogenated alkyl having 1 to 10 carbon atoms.
Wherein the purine functional group is formed from a compound represented by the following Chemical Formula 3c to 3h.
Wherein R 12 to R 25 may be the same or different from each other and each independently represents H, D, F, Cl, Br, I, an amino group, a straight chain alkyl having 1 to 12 carbon atoms, a carboxyl group having 1 to 10 carbon atoms An acid, an alcohol having 1 to 10 carbon atoms, and a halogenated alkyl having 1 to 10 carbon atoms.
i) dissolving the organic luminescent compound in a solvent to prepare a solution;
ii) preparing a substrate;
iii) applying the solution of step i) to one side of the substrate;
iv) heat treating the substrate coated with the solution for a predetermined time to form a thin film;
Wherein the organic thin film layer is formed on the substrate.
Wherein the organic light emitting compound is soluble in the solvent at room temperature in step i).
Further comprising the step of adding a luminescent dopant to the solution between the step i) and the step ii).
The solvent in step i) may be one or more selected from the group consisting of 1,2,3-Trichlorobenzene, 1,2,4-Trichlorobenzene, 1,3,5-Trichlorobenzene, chloroform, tetrahydrofuran, Wherein the organic solvent is a mixed solvent containing at least two organic solvents.
Wherein the step iv) comprises forming a thin film by hydrogen bonding in a functional period including the pyrimidine ring provided in the organic light emitting compound.
And the step iv) is performed at a temperature of 70 to 170 ° C.
The step iii) may be carried out by any one method selected from the group consisting of spin coating, gravure offset printing, reverse offset printing, screen printing, roll-to-roll printing, slot die coating, dip coating, spray coating, doctor blade coating, Wherein the organic thin film layer is formed on the substrate.
Wherein the organic device is selected from organic light emitting devices, organic photoconductors, organic transistors, organic solar cells, and organic image sensors.
Preparing a substrate;
ii) forming an anode on the substrate;
iii) forming a hole injection layer on the anode;
iv) forming a hole transport layer on the hole injection layer;
v) forming a light emitting layer on the hole transport layer;
vi) forming an electron transport layer on the light emitting layer;
vii) forming a cathode on the electron transport layer; , ≪ / RTI >
Wherein the light emitting layer in step vi) is formed by the method of manufacturing the organic thin film layer according to claim 10.
Wherein the step iii), the step iv), and the step v) are performed through a solution process.
Further comprising the step of forming a hole blocking layer between the step v) and the step vi).
And forming an electron injection layer between the step vi) and the step vii).
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| PCT/KR2016/010717 WO2017052308A2 (en) | 2015-09-25 | 2016-09-23 | Organic compound to be used in organic device, and method for manufacturing organic device by using same |
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| KR20190087853A (en) | 2018-01-17 | 2019-07-25 | 한국생산기술연구원 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20190102586A (en) | 2018-02-26 | 2019-09-04 | 한국생산기술연구원 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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| KR20190087853A (en) | 2018-01-17 | 2019-07-25 | 한국생산기술연구원 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20190102586A (en) | 2018-02-26 | 2019-09-04 | 한국생산기술연구원 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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| KR20200094399A (en) | 2019-01-30 | 2020-08-07 | 한국생산기술연구원 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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| KR20210097497A (en) | 2020-01-30 | 2021-08-09 | 한국생산기술연구원 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR102289502B1 (en) | 2020-02-04 | 2021-08-13 | 한국생산기술연구원 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20220143516A (en) | 2021-04-16 | 2022-10-25 | 한국생산기술연구원 | Compound for organic electronic element having benzenesulfonate functional group, organic electronic element using the same, and an electronic device thereof |
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