CN1802053A - Organic luminescent device based on cyanate compound - Google Patents
Organic luminescent device based on cyanate compound Download PDFInfo
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Abstract
Said invention provides an Organic Light Emitting Display (OLED) to solve luminescent material service life problem. It features functional layer containing cyanate compound held between anode and cathode, said invention also includes Organic Light Emitting Display (OLED) manufacturing method.
Description
Technical Field
The present invention relates to cyanate ester compounds, and more particularly, to a device for emitting light by applying an electric field to a functional layer containing the cyanate ester compounds.
Background
Since Organic Light Emitting Diodes (OLEDs) have many advantages of self-luminescence, thin thickness, fast response speed, wide viewing angle, good resolution, high brightness, etc., they are considered as a new generation of flat panel display technology that can replace liquid crystal displays in the future. In the organic light-emitting device, a thin film containing a fluorescent organic compound is sandwiched between an anode and a cathode, electrons or holes are injected from the respective electrodes, the electrons and holes are combined with each other in a light-emitting layer, and the resulting energy generates an exciton of a fluorescent compound molecule, and the exciton emits light when returning to a ground state, and the organic light-emitting device utilizes the emitted light.
Since various fluorescent organic compounds emit light from ultraviolet to infrared by changing the kind thereof, various luminescent compounds have been actively studied. Patent applications in various countries are also disclosed in, for example, U.S. Pat. No. 5151629, U.S. Pat. No. 5409783, Japanese patent application laid-open No. Hei 2-247278, and Japanese patent application laid-open No. Hei 3-255190.
In addition to the organic light emitting devices using the above-described small molecule materials, an organic light emitting device using a conjugated polymer has been reported by a group of Cambridge university (Cambridge university) (nature, 347, 539 (1990)). The report has disclosed that a polyphenylene vinylene (PPv) film is formed by a coating method and confirmed that the film is a single layer light emitting film. Examples of patents relating to organic light-emitting devices using conjugated polymers include U.S. Pat. No. 5247190, U.S. Pat. No. 5514878, JP-A-4-145192, and JP-A-5-247460.
At present, organic light emitting devices have been remarkably developed, and have been widely used because of their characteristics such as high luminance, high-speed response, and various emission wavelengths, compared with current display technologies. However, problems in durability such as deterioration due to aging after long-term use, poor thermal stability, or deterioration due to an atmospheric gas containing oxygen, moisture, and the like have not been solved. Therefore, if the organic light emitting device display technology is applied in a large scale, the problem of the lifetime of the light emitting material must be solved.
Disclosure of Invention
The invention aims to provide an organic electroluminescent device with good stability of an organic luminescent material, and solve the problem of service life of the existing luminescent material.
The functional layer material of the organic light-emitting device contains cyanate compounds.
In a general sense, cyanate ester monomers are defined as compounds containing two or more cyanate ester functional groups, and we define cyanate ester monomers herein as two classes: monofunctional cyanate monomer (chemical formula is expressed as: monofunctional monomer R-O-C.ident.N) and multifunctional cyanate monomer (containing bifunctional monomer N.ident.C-O-R-O-C.ident.N and cyanate monomer R- (O-C.ident.N) containing more than two functional groups)n(n is a constant, n.gtoreq.3)). For polyfunctional cyanate monomersThe two or more cyanate groups may be on the same carbon atom or on a plurality of carbon atoms. Here, the cyanate ester compound is defined as a compound obtained by a reaction between at least two different cyanate ester monomers belonging to the above two classes.
Wherein R independently represents a substituted or unsubstituted alkyl group, and may, for example, be a difluoromethyl group, an isopropyl group or the like; the alkenyl group may be a substituted or unsubstituted alkenyl group, a conjugated alkenyl group or an alkynyl group, and may, for example, be a vinyl group, an isopropenyl group, a butadienyl group, an octatetraenyl group or the like; substituted or unsubstituted amino, nitro, cyano, alkoxy, thioether, sulfur, silicon, and the like; examples of the substituted or unsubstituted aralkyl group include benzyl and phenethyl; examples of the substituted or unsubstituted aryl group include phenyl, dry-toluene, and tri-dry-toluene; examples of the heterocyclic group which may be substituted orunsubstituted (containing a heteroaromatic group) include a pyrrolyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a trithiolyl group, an imidazolyl group, a pyridyl group, a furyl group, a piperidyl group, a benzoxazolyl group, a thienyl group, a triazolyl group and a carbazolyl group; examples of the substituted or unsubstituted condensed polycyclic aromatic group include fluorenyl, naphthyl, fluoranthenyl, anthryl, phenanthryl, pyrenyl, tetracenyl, pentacenyl, benzophenanthryl and perylenyl; examples of the substituted or unsubstituted condensed polycyclic heterocyclic group include acridine group, phenanthroline group and the like.
The cyanate ester monomer of the present invention can be synthesized and obtained by a known method, for example, a synthesis method:
stroh and Gerber gave cyanate esters with ortho-substituted phenols in 1960. Martin in the same year found that pyrolysis of 1, 2, 3, 4-thiotriazole can also be used to synthesize cyanate ester, but the cost is too high.
Most alkyl cyanates will isomerize quickly to the more stable isocyanate form, but the cyanates of the bicyclic alcohols with the hydroxyl group in the bridgehead position and the acidic alcohols containing electronegative substituents (e.g., halogens) will not isomerize.
Grigat and Putter used the above reaction to prepare a series of aromatic cyanate ester resins in 1963. The invention is the basis for the commercial application of cyanate ester.
Martin, Jensen and Holm simultaneously obtain a series of aliphatic and simple aromatic cyanate in 1964.
Cyanate ester was commercialized by Bayer corporation in germany in 1967.
Since the eighties, new cyanate ester resins such as fluorine substituted, multifunctional cyanate ester resins were synthesized.
The synthesis of cyanate ester resin monomers has been extensively discussed in many documents and can be carried out in a variety of ways. However, only one method for preparing high temperature resistant thermosetting resin is really promising for industrialization, namely, cyanogen halide reacts with phenolic compound in the presence of alkali to prepare cyanate ester resin monomer. The reaction is as follows, taking Br as an example:
the synthesis process can be divided into a one-step method and a two-step method: a one-step method: refers to a method for preparing cyanate by directly using cyanide (such as potassium cyanide, sodium cyanide and the like) to react with phenolic compounds. The synthesis process comprises the following steps: firstly, cooling the water solution of bromine or chlorine to low temperature by using refrigerants such as solid alcohol and the like, then slowly adding the water solution of potassium cyanide or sodium cyanide while stirring, and then adding a phenol solution and an alkali liquor to obtain a mixture containing cyanate. After a series of complicated separation and purification processes, the cyanate ester monomer product is obtained. The method has the advantages of low cost, long reaction time, complex purification process, low yield and purity, and difficult treatment of more cyanides in waste liquid, so that the method is rarely used for synthesizing the cyanate monomer at present. The two-step method comprises the following steps: refers to a method of first preparing cyanogen halide and then synthesizing cyanate ester in another reaction system. The technological process includes cooling phenol solution to low temperature, adding prepared cyanogen bromide or cyanogen chloride solution slowly into the reaction system, stirring vigorously, adding alkali solution while controlling the dropping speed of alkali solution and maintaining the dosage less than cyanogen halide, and reaction at-30-0 deg.c. After the reaction is finished, the product is separated and purified, and the yield is 70-80%. The method has the advantages of high reaction speed, easy separation and purification of products, high purity of prepared cyanate, high cost, easy generation of virulent hydrocyanic acid in the reaction, high operational risk and need of careful protective measures.
Some cyanate ester monomers which have been industrially produced at present:
in the aspect of home-made: bisphenol A cyanate ester resin (melting point 79 ℃, molecular weight 278, purity ≦ 70%);
in foreign aspects: the corresponding molecular structures of the common seven brands of cyanate ester commercial products are shown in the following figures:
The Structure of Cyanate Ester Resins
whereinEtc. may be used as monomers for the organic material in the device of the present invention.
Most of cyanate monomers are solid or semi-solid substances at normal temperature, and can be dissolved in common solvents such as acetone, butanone, chloroform, tetrahydrofuran, dichloromethane and the like. After the cyanate monomer is heated and melted, the viscosity of the cyanate monomer is only 0.15-0.5Pa.s, and the cyanate monomer has good wettability and adhesiveness, so that a proper molding process and equipment can be selected according to actual requirements in application.
The cyanate estermonomer has a relatively simple curing behavior (curing may be considered as a chemical reaction including a reaction between monofunctional monomers and polyfunctional monomers, and also including a polymerization reaction between polyfunctional monomers), in the presence of active hydrogen (e.g., water (HOH), hydrohalic acid (HX), alcohol (ROH), ammonia NH, etc.)3) Phenol (ArOH), etc.) or metal ions (e.g. Zn)2+、Al3+Ionic compounds of nickel (Ni), cobalt (Co), etc., including transition metal ionic compounds) in the presence of or in a high-temperature environment, a cyclotrimerization reaction (cyclotrimerization) is likely to occur to form a triazine ring-containing high-crosslinking-degree network structure macromolecule, and the curing reaction temperature ranges are as follows: -20 ℃ C-300 ℃. The reaction formula is as follows:
the functional group structure of the cyanate resin is-O-C [ identical to]N, one sigma bond and two pi bonds are arranged in a triple bond, and the binding force of an atomic nucleus to pi electrons is small, so that the pi electrons are high in mobility and easy to break, and therefore the reaction is easy to occur.
The cyanate compound obtained after the curing reaction of the monofunctional cyanate monomer and the multifunctional cyanate monomer has the following structure:
wherein R is1-R6，R1、R2And R3Independently represent a substituted or unsubstituted alkyl group, and may, for example, be difluoromethyl, isopropyl, etc.; the alkenyl group may be a substituted or unsubstituted alkenyl group, a conjugated alkenyl group or an alkynyl group,and may, for example, be a vinyl group, an isopropenyl group, a butadienyl group, an octatetraenyl group or the like; substituted or unsubstituted amino, nitro, cyano, alkoxy, thioether, sulfur, silicon, and the like; examples of the substituted or unsubstituted aralkyl group include benzyl and phenethyl; examples of the substituted or unsubstituted aryl group include phenyl, dry-toluene, and tri-dry-toluene; examples of the heterocyclic group which may be substituted or unsubstituted (containing a heteroaromatic group) include a pyrrolyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a trithiolyl group, an imidazolyl group, a pyridyl group, a furyl group, a piperidyl group, a benzoxazolyl group, a thienyl group, a triazolyl group and a carbazolyl group; examples of the substituted or unsubstituted condensed polycyclic aromatic group include fluorenyl, naphthyl, fluoranthenyl, anthracenyl, phenanthrenyl, pyrenyl, tetracenyl, pentacenyl, benzophenanthrenyl and anthryl; examples of the substituted or unsubstituted condensed polycyclic heterocyclic group include acridine group, phenanthroline group and the like. Wherein the monofunctional group monomer can be used as a blocking group for the reaction of the multifunctional cyanate monomer. Of course, the cyanate ester compound in the functional layer may be directly generated by the curing reaction of the cyanate ester monomer in the production process of the light-emitting device, or may be a compound (or a compound) having the same structureObtained by also not by a curing reaction of the monomers) to form the functional layer directly from the compound (without the monomers) under appropriate conditions (melt, solution, etc.), provided of course that the resulting compound must have an appropriate melting point, solubility, etc. for processing.
The cyanate monomer is cyclized and trimerized to form a network structure consisting of triazine rings, so that the whole macromolecule is a resonance system and has some excellent mechanical and thermal properties. Such as: under the action of an electromagnetic field, the cyanate ester compound has a very low dielectric loss factor, and is insensitive to polarization relaxation and the like when the frequency is changed, so that the cyanate ester compound has broadband dielectric characteristics. The dielectric constant of the cyanate ester compound is between 2.6 and 3.2. The dielectric constant of the cyanate ester compound can be further reduced by using a dicyclopentadiene spacer (spacer) to increase the length of the bisphenol main chain. The dielectric loss factor of the cyanate ester compound is between 0.002 and 0.008. Moreover, the cyanate ester compound can better keep lower dielectric constant and dielectric loss factor than other thermosetting resins under high temperature and humid conditions and in a wider frequency range. The excellent dielectric property enables the cyanate ester resin to have great advantages in the fields of circuit design and microwave transmission. Thermal properties: the glass transition temperature of the bisphenol A cyanate ester compound is between 250 ℃ and 290 ℃. Increasing the length of the bisphenol backbone reduces the dielectric constant of the cyanate ester resin, but also increases TgAnd (4) descending. The initial weight loss temperature of the cyanate compound is within the range of 385-431 ℃, and the service life of the cyanate compound is 25,000h at the temperature of 162-180 ℃. Moisture resistance and chemical stability: the moisture resistance of the polymer depends on the chemical structure of the polymer, and cyanate compounds do not contain easily hydrolyzable groups such as ester groups, amide groups and the like, so the moisture resistance of the polymer is better. High pressure steam testing at 121 ℃ showed that ortho-methylation of the bisphenol precursor (precorsor) increased the initial hydrolysis time of the fully converted cyanate compound from 200h to>600h, probably due to steric hindrance, which prevented the water molecule from attacking the triazine nucleus. The cyanate ester compound has good chemical resistance. P-benzene, dimethyl formamide, formaldehyde, fuel oil, petroleum, concentrated acetic acid, trichloroacetic acid and sodium phosphate concentrated solutionAnd 30% H2SO4And (4) stabilizing. But is easily attacked by 25% ammonia, 4% aqueous NaOH, 50% nitric acid and concentrated sulfuric acid, and the hydrolysis is accompanied by surface passivation and corrosion.
In addition, the cyanate compound contains a large amount of nitrogen atoms, and the nitrogen atoms can be connected with the metal through interaction between electrons and holes due to the self structural factor of the cyanate compound, so the cyanate compound can be tightly combined with the cathode and the anode with the metal and the metal oxide, and the transmission of the electrons and the holes is more convenient and rapid.
In addition, the molecular weight and the film thickness of the cyanate ester compound obtained after the reaction of the cyanate ester monomer can be regulated and controlled by adjusting the concentration of the cyanate ester monomer solution, the coating thickness of the cyanate ester monomer melt, the curing temperature, the curing agent and the like in different coating processes; the mono-cyanate functional monomer can be used as a terminal blocking group of the multifunctional monomer, and with the increase of the number of the mono-cyanate functional monomers, the reaction between the multifunctional cyanate monomers or between the multifunctional cyanate monomers is reduced, so that the reaction tends to be terminated, and the molecular weight of the cured compound is reduced, therefore, the proper molecular weight compound can be obtained by controlling the proportion of the mono-cyanate functional monomer to the multifunctional cyanate monomer; meanwhile, the purpose of designing the chemical structure of the final product can be achieved by adopting the mixture of cyanate monomers with different structures. It can be said that the mixture of cyanate monomers with different structures in a certain proportion can meet the requirements of variable molecular weight and designable chemical structure of the final product. And the relevant ones of the process are melt coating thickness, curing temperature, curing agent, etc.; the coating process herein refers to a process method including a vacuum evaporation method, a solution coating method (including printing), a melt coating method (including printing), and the like, that is, a method of forming a functional layer.
The compound of the present invention is superior to conventional compounds in durability, and is used for layers containing an organic compound, particularly an electron transporting layer, a hole transporting layer and a light emitting layer, of an organic light emitting device, and layers formed by a vacuum evaporation method, a solution coating method, a melt coating method, or the like, is not crystallized, and has excellent stability with time.
Hereinafter, the organic light emitting device of the present invention is described in detail.
The organic light-emitting device of the present invention comprises at least one pair of electrodes (comprising an anode and a cathode) and one or more layers containing an organic compound sandwiched between the pair of electrodes, wherein at least one layer containing an organic compound contains at least one of the compounds represented by the present invention described above.
In the organic light-emitting device of the present invention, it is preferable that at least one of the electron-transporting layer, the hole-transporting layer, and the light-emitting layer contains at least one of the compounds in the layer containing an organic compound. That is, the cyanate ester monomer or compound of the present invention can be doped with other functional materials or metal ion compounds.
In the organic light-emitting device of the present invention, the above-mentioned cyanate ester-based monomer is formed between the anode and the cathode by a vacuum evaporation method, a printing method, or a solution or melt coating method, and then cured to produce a compound. The compound organic layer is preferably formed into a thin film having a thickness of less than 10 μm, more preferably 0.5 μm or less, particularly preferably 0.01 to 0.5. mu.m. The molecular weight and the film thickness of the compound can be regulated and controlled by adjusting the concentration of a cyanate monomer solution, the proportion of the cyanate monomer, the melt coating thickness of the cyanate monomer, the curing temperature, the curing agent and the like.
In the organic light emitting device of the present invention, the anode material can have as large a work function as possible. For example, a single metal material such as gold, platinum, nickel, palladium, cobalt, selenium, and vanadium or an alloy thereof; metal oxides such as tin oxide, zinc oxide, indium-tin oxide (ITO), and indium-zinc oxide. In addition, conductive polymers such as polyaniline, polypyrrole, polythiophene, or poly (phenylene sulfide) can also be used. Any of these electrode materials may be used alone, or a plurality of electrode materials may be used in combination.
On the other hand, it is preferable that the cathode material has a small work function. For example, a single metal material such as lithium, sodium, potassium, cesium, calcium, magnesium, aluminum, indium, silver, lead, tin, and chromium may be used, or an alloy using a plurality of substances may be used. Metal oxides such as Indium Tin Oxide (ITO) may also be used. In addition, the cathode may have a single-layer structure or a multi-layer structure.
Drawings
A more complete appreciation of the invention and many of the attendant advantages thereof will be readily apparent as the same becomes better understood by reference to the following detailed description of exemplary embodiments thereof when considered in connection with the accompanying drawings. Fig. is a sectional view of an organic electroluminescent display according to an embodiment of the present invention; in the pattern, the device consists of an anode 2, an organic functional layer 3 and a cathode 4, which are formed in sequence on a substrate 1, the uppermost of which is covered with a substrate 5.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
In the drawings, preferred embodiments of the organic light emitting device of the present invention are shown. As shown in the drawing, the material of the anode 2 may have as large a work function as possible. For example, a single metal material such as gold, platinum, nickel, palladium, cobalt, selenium, and vanadium or an alloy thereof; metal oxides such as tin oxide, zinc oxide, indium-tin oxide (ITO), and indium-zinc oxide. Any of these electrode materials may be used alone, or a plurality of electrode materials may be used in combination. It is preferable that the material of the cathode 4 has a small work function. For example, a single metal material such as lithium, sodium, potassium, cesium, calcium, magnesium, aluminum, indium, silver, lead, tin, and chromium may be used, or an alloy using a plurality of substances may be used. Metal oxides such as Indium Tin Oxide (ITO) may also be used. In addition, the cathode 4 may be a single-layer structure or a multi-layer structure. Wherein, the organic functional layer 3 comprises a cyanate ester based compound: preparing a cyanate monomer solution with a certain proportion by using solvents such as acetone and the like, and coating the solution on the surface of the anode; the cyanate ester monomer can be heated to the melting temperature and coated on the surface of the anode through the melt, such as bisphenol A cyanate ester resin (the melting point is 79 ℃, and the viscosity is 0.29Pa&s); in the presence of active hydrogen (e.g. water (HOH), hydrohalic acid (HX), alcohol (ROH), ammonia (NH)3) Phenol (ArOH), etc.) or metal ions (e.g. Zn)2+、Al3+Nickel (N)i) Cobalt (Co) ionic compounds, etc., containingTransition metal ion compound) (in the presence of active hydrogen or metal ions, the curing temperature range of the cyanate monomer is as follows: -20 ℃ to 300 ℃) or at high temperature (>250 ℃), a curing reaction:
wherein the compound of the cured monofunctional cyanate monomer and the multifunctional cyanate monomer has the following structures:
wherein R is1-R6，R1、R2And R3Independently represent a substituted or unsubstituted alkyl group, and may, for example, be difluoromethyl, isopropyl, etc.; the alkenyl group may be a substituted or unsubstituted alkenyl group, a conjugated alkenyl group or an alkynyl group, and may, for example, be a vinyl group, an isopropenyl group, a butadienyl group, an octatetraenyl group or the like; substituted or unsubstituted amino, nitro, cyano, alkoxy, thioether, sulfur, silicon, and the like; examples of the substituted or unsubstituted aralkyl group include benzyl and phenethyl; examples of the substituted or unsubstituted aryl group include phenyl, dry-toluene, and tri-dry-toluene; examples of the heterocyclic groupwhich may be substituted or unsubstituted (containing a heteroaromatic group) include a pyrrolyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a trithiolyl group, an imidazolyl group, a pyridyl group, a furyl group, a piperidyl group, a benzoxazolyl group, a thienyl group, a triazolyl group and a carbazolyl group; examples of the substituted or unsubstituted condensed polycyclic aromatic group include fluorenyl, naphthyl, fluoranthenyl, anthryl, phenanthryl, pyrenyl, tetracenyl, pentacenyl, benzophenanthryl and perylenyl; examples of the substituted or unsubstituted condensed polycyclic heterocyclic group include acridine group, phenanthroline group and the like.
The present invention may, of course, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the invention to those skilled in the art. In the drawings, the thickness of layers and regions are exaggerated for clarity.
The above examples are given solely for the purpose of illustration and are not to be construed as limitations of the present invention, the scope of which is defined by the claims, and which are intended to encompass variations and modifications that will be apparent to those skilled in the art.
Claims (6)
1. An organic light-emitting device having a functional layer sandwiched between an anode and a cathode, wherein the functional layer contains a cyanate ester compound.
2. The organic light emitting device of claim 1, wherein the cyanate ester compound has the structure:
wherein R is1-R6，R1、R2And R3Independently represent a substituted or unsubstituted alkyl group, and may, for example, be difluoromethyl, isopropyl, etc.; the alkenyl group may be a substituted or unsubstituted alkenyl group, a conjugated alkenyl group or an alkynyl group, and may, for example, be a vinyl group, an isopropenyl group, a butadienyl group, an octatetraenyl group or the like; substituted or unsubstituted amino, nitro, cyano, alkoxy, thioether, sulfur, silicon, and the like; examples of the substituted or unsubstituted aralkyl group include benzyl and phenethyl; examples of the substituted or unsubstituted aryl group include phenyl, dry-toluene, and tri-dry-toluene; examples of the heterocyclic group which may be substituted or unsubstituted (containing a heteroaromatic group) include a pyrrolyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a trithiolyl group, an imidazolyl group, a pyridyl group, a furyl group, a piperidyl group, a benzoxazolyl group, a thienyl group, a triazolyl group and a carbazolyl group; examples of the substituted or unsubstituted condensed polycyclic aromatic group include fluorenyl, naphthyl, fluoranthenyl, anthryl, phenanthryl, pyrenyl, tetracenyl, pentacenyl, benzophenanthryl and perylenyl; examples of the substituted or unsubstituted condensed polycyclic heterocyclic group include acridine group, phenanthroline group and the like.
3. An organic light-emitting device according to claim 1, comprising at least one pair of electrodes (comprising an anode and a cathode) and one or more layers containing an organic compound sandwiched between the pair of electrodes, wherein at least one layer containing an organic compound contains at least one compound represented by claim 2.
4. The organic light emitting device of claim 1, wherein the cyanate ester compound has a certain molecular weight and a certain thickness, and the cyanate ester compound can be coated by proper solution concentration of the cyanate ester monomer, proper ratio of monomers (mono-cyanate ester functional group and poly-cyanate ester functional group monomers), proper melt coating thickness of the cyanate ester monomer, proper curing temperature, and proper curing agent according to different coating processes.
5. The organic light emitting device of claim 4, wherein the coating process may employ a vacuum evaporation method, a melt coating method, a solution coating method, or the like.
6. An organic light-emitting device according to claim 4, wherein the curing agent for the cyanate ester monomer is selected from metal ion compounds, such as Zn2+、Al3+Metal ion compounds such as nickel (Ni) and cobalt (Co) or active hydrogen-containing compounds such as water (HOH), hydrohalic acid (HX), alcohol (ROH), and ammonia (NH)3) Phenol (ArOH), and the like.
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