CN111344288B - Novel heterocyclic compound and organic light-emitting device using same - Google Patents
Novel heterocyclic compound and organic light-emitting device using same Download PDFInfo
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Abstract
The present invention provides a novel heterocyclic compound and an organic light-emitting device using the same.
Description
Technical Field
The present application claims priority based on korean patent application No. 10-2018-0054366 at 11 of 5 months of 2018 and korean patent application No. 10-2019-0054491 at 9 of 5 months of 2019, the entire contents of the disclosures of which are incorporated as part of the present specification.
The present invention relates to a novel heterocyclic compound and an organic light-emitting device including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from the anode to the organic layer, electrons are injected from the cathode to the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state.
As for the organic matter used for the organic light emitting device as described above, development of new materials is continuously demanded.
Prior art literature
Patent literature
(patent document 0001) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Problems to be solved
The present invention relates to a novel heterocyclic compound and an organic light-emitting device including the same.
Solution to the problem
The present invention provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
X 1 to X 3 Each independently is N or CR 2 ，X 1 To X 3 More than 1 of them is N,
Y 1 to Y 3 Each independently is N or CR 3 ，Y 1 To Y 3 More than 1 of them is N,
q is O or S, and the total number of the components is O or S,
Ar 1 to Ar 5 Each independently is a substituted or unsubstituted C 6-60 An aryl group; substituted or unsubstituted C comprising more than 1 hetero atom selected from O, N, si and S 1-60 Heteroaryl, or Ar 1 To Ar 5 Are combined with groups adjacent to each other to form condensed rings,
L 1 to L 4 Each independently is a single bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C containing more than 1 hetero atom selected from O, N, si and S 1-60 A heteroarylene group,
R 1 to R 3 Each independently is hydrogen; deuterium; halogen; cyano group; a nitro group; an amino group; substituted or unsubstituted C 1-60 An alkyl group; substituted or unsubstituted C 1-60 A haloalkyl group; substituted or unsubstituted C 1-60 An alkoxy group; substituted or unsubstituted C 1-60 Haloalkoxy groups; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl groups; substituted or unsubstituted C 6-60 An aryl group; substituted or unsubstituted C 6-60 An aryloxy group; or substituted or unsubstituted C containing more than 1 hetero atom selected from N, O and S 1-60 A heteroaryl group, which is a group,
n1 is an integer of 0 to 4,
n2 is an integer of 0 to 3,
n3 is an integer from 0 to 4.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 can be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, lower driving voltage and/or improvement of lifetime characteristics can be achieved.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, an electron transport layer 8, an electron injection layer 9, and a cathode 4.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
The present invention provides a compound represented by the above chemical formula 1.
In the present description of the invention,
refers to a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio group [ ]
Alkylthio) is described; arylthio (/ ->
Aryl thio xy); alkylsulfonyl (+)>
Alkylsulfoxy); arylsulfonyl (+)>
Aryl sulfoxy); a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a substituent containing 1 or more of N, O and 1 or more of the heteroaryl groups of S atoms is substituted or unsubstituted, or a substituent linked with 2 or more of the above-exemplified substituents is substituted or unsubstituted. For example, when "a substituent in which 2 or more substituents are linked" is a biphenyl group, the biphenyl group may be interpreted as an aryl group substituted with 1 phenyl group, or a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but the present invention is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,
A base, etc., but is not limited thereto.
In the present specification, the heteroaryl group is a heteroaryl group containing 1 or more of O, N, si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. As heteroaryl groupsExamples of (C) are thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl,
Azolyl, (-) -and (II) radicals>
Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->
Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the above-described examples of the aryl group. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, or alkylamino group is the same as the examples of the alkyl group described above. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heteroaryl group. In this specification, alkenyl groups in aralkenyl groups are the same as the above-described examples of alkenyl groups. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied in addition to this. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heteroaryl group can be applied thereto. In this specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied. In this specification, a heterocyclic ring is not a 1-valent group but a combination of 2 substituents, and the above description of heteroaryl groups can be applied thereto.
On the other hand, in the above chemical formula 1, ar 1 To Ar 3 May each independently be substituted or unsubstituted C 6-60 Aryl groups.
For example, ar 1 To Ar 3 May be phenyl.
Preferably, in the above chemical formula 1, L 1 To L 3 Each independently may be a single bond, or a substituted or unsubstituted C 6-60 Arylene groups.
For example, L 1 To L 3 May be a single bond.
Preferably, the above chemical formula 1 may be any one of the compounds of the following chemical formulas 2 to 5.
[ chemical formula 2]
[ chemical formula 3]
[ chemical formula 4]
[ chemical formula 5]
In the above, for X 1 To X 3 、Y 1 To Y 3 、Q、L 4 、Ar 4 、Ar 5 The description of n2 and n3 is the same as defined above.
Preferably, in the above chemical formula 1, ar 4 And Ar is a group 5 Each independently is a substituted or unsubstituted C 6-60 Aryl groupOr Ar 4 And Ar is a group 5 May be combined with groups adjacent to each other to form a fused ring.
Preferably, in the above chemical formula 1, L 4 May be a single bond, phenylene, pyridyldiyl, biphenyldiyl, or naphthylene.
For example, the above-mentioned compounds may be selected from the following compounds:
on the other hand, as an example, the compound represented by the above chemical formula 1 can be produced by a production method shown in the following reaction formula 1.
[ reaction type 1]
In the above reaction formula 1, the definitions other than X are the same as those described above, and X is halogen, more preferably bromine or chlorine.
The reaction is a suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the suzuki coupling reaction may be modified as known in the art. The above-described production method can be more specifically described in the production example described later.
In addition, the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. As one example, the present invention provides an organic light emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above light emitting layer.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, an electron transport layer 8, an electron injection layer 9, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in 1 or more layers among the above hole injection layer, hole transport layer, electron blocking layer, light emitting layer, electron transport layer, and electron injection layer.
Specifically, the organic layer may include a light-emitting layer, and the light-emitting layer may contain 2 or more host substances.
In this case, the 2 or more host substances may include a compound represented by the chemical formula 1.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the above organic layers include the compound represented by chemical formula 1. In addition, in the case where the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be manufactured as follows: PVD (physical Vapor Deposition) process such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to vapor-deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, the compound represented by the above chemical formula 1 may be used not only in a vacuum deposition method but also in a solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO: al or SNO 2 : a combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and as a hole-transporting substance, a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, a substance having a large mobility to the holes is preferable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and preferably has high quantum efficiency for fluorescence or phosphorescence. As a specific example, there is 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (E
Azole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene; rubrene, etc., but is not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
Pyrimidine derivatives, etc., but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,
Bisindenopyrene, etcThe styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and is preferably a substance having high mobility for electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,/->
Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and their derivatives, metal complexes, and nitrogen-containing penta-compoundsAnd ring-membered derivatives, but are not limited thereto. />
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically described in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
Production example 1: production of intermediate 1A
After dispersing 2-chloro-4- (4-chlorophenyl) -6-phenyl-1,3,5-triazine (30.0 g,99.7 mmol) and 2,4-diphenyl-6- (2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine (43.4 g,99.7 mmol) in tetrahydrofuran (300 mL), 2M aqueous potassium carbonate (aq.K) 2 CO 3 ) (150 mL) was added tetrakis (triphenylphosphine) palladium [ Pd (PPh) 3 ) 4 ](3.5 g,3 mol%) was followed by stirring and refluxing for 12 hours. The temperature was lowered to room temperature, and the resulting solid was filtered. The filtered solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered and dried, whereby compound 1A (33.7 g, yield 59%) was produced.
MS：[M+H] + ＝575
Production example 2: production of intermediate 1B
After 2-chloro-4- (3-chlorophenyl) -6-phenyl-1,3,5-triazine (30.0 g,99.7 mmol) and 2,4-diphenyl-6- (2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine (2, 4-diphenoyl-6- (2- (4, 5-tetramethy-l-1, 3, 2-dioxabilian-2-yl) phenyl) -1,3, 5-triazine) (43.4 g,99.7 mmol) were dispersed in tetrahydrofuran (300 mL), 2M aqueous potassium carbonate (aq.K) 2 CO 3 ) (150 mL) was added tetrakis (triphenylphosphine) palladium [ Pd (PPh) 3 ) 4 ](3.5 g,3 mol%) was followed by stirring and refluxing for 12 hours. The temperature was lowered to room temperature, and the resulting solid was filtered. The filtered solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered and dried, whereby compound 1B (28.0 g, yield 49%) was produced.
MS：[M+H] + ＝575
Production example 3: production of intermediate 1C
After dispersing 2-chloro-4- (2-chlorophenyl) -6-phenyl-1,3,5-triazine (2-chloro-4- (2-chloropheny l) -6-phenyl-1,3, 5-triazine) (30.0 g,99.7 mmol) and 2,4-diphenyl-6- (2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine (2, 4-diphenoyl-6- (2- (4, 5-tetramethy-l-1, 3, 2-dioxab-orolan-2-yl) -1,3, 5-triazine) (43.4 g,99.7 mmol) in tetrahydrofuran (300 mL), 2M aqueous potassium carbonate solution (aq.K 2 CO 3 ) (150 mL) was added tetrakis (triphenylphosphine) palladium [ Pd (PPh) 3 ) 4 ](3.5 g,3 mol%) was followed by stirring and refluxing for 12 hours. The temperature was lowered to room temperature, and the resulting solid was filtered. The filtered solid was treated with tetrahydrofuran and ethyl acetateThe ester was recrystallized, filtered and dried, whereby compound 1C (30.3 g, yield 53%) was produced.
MS：[M+H] + ＝575
Example 1: production of Compound 1
Compound 1A (20.0 g,34.8 mmol) and dibenzo [ b, d ] were reacted under nitrogen atmosphere]Furan-4-ylboronic acid (11.1 g,52.3 mmol) was added to the bis (O-L)
In alkane (200 mL), stir and reflux. Then, potassium carbonate (14.4 g,104.5 mmol) was dissolved in water (60 mL) and then stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.5 g,1.0 mmol) was added thereto. After 2 hours of reaction, the temperature was lowered to room temperature and filtration was performed. After the filtrate was extracted with chloroform and water, the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, and then recrystallized using a mixed solution of tetrahydrofuran and ethyl acetate. The resultant solid was filtered and dried to produce compound 1 (17.5 g, yield 71%).
MS：[M+H] + ＝707
Example 2: production of Compound 2
The above-mentioned compound 2 (16.1 g, 66%) was produced by the same method as the method for producing compound 1 in example 1, except that dibenzo [ b, d ] furan-3-ylboronic acid was used instead of dibenzo [ b, d ] furan-4-ylboronic acid.
MS：[M+H] + ＝707
Example 3: production of Compound 3
The above-mentioned compound 3 (17.2 g, 70%) was produced by the same method as the method for producing compound 1 in example 1, except that dibenzo [ b, d ] furan-2-ylboronic acid was used instead of dibenzo [ b, d ] furan-4-ylboronic acid.
MS：[M+H] + ＝707
Example 4: production of Compound 4
The above-mentioned compound 4 (10.3 g, 42%) was produced by the same method as the method for producing compound 1 in example 1, except that dibenzo [ b, d ] furan-1-ylboronic acid was used instead of dibenzo [ b, d ] furan-4-ylboronic acid.
MS：[M+H] + ＝707
Example 5: production of Compound 5
The above-mentioned compound 5 (16.6 g, 66%) was produced by the same method as the method for producing compound 1 in example 1, except that dibenzo [ b, d ] thiophen-4-ylboronic acid was used instead of dibenzo [ b, d ] furan-4-ylboronic acid.
MS：[M+H] + ＝723
Example 6: production of Compound 6
The above-mentioned compound 6 (19.6 g, 78%) was produced by the same method as the method for producing compound 1 in example 1, except that dibenzo [ b, d ] thiophen-3-ylboronic acid was used instead of dibenzo [ b, d ] furan-4-ylboronic acid.
MS：[M+H] + ＝723
Example 7: production of Compound 7
The above-mentioned compound 7 (7.3 g, 29%) was produced by the same method as the method for producing compound 1 in example 1, except that dibenzo [ b, d ] thiophen-2-ylboronic acid was used instead of dibenzo [ b, d ] furan-4-ylboronic acid.
MS：[M+H] + ＝723
Example 8: production of Compound 8
The above-mentioned compound 8 (11.0 g, 44%) was produced by the same method as the method for producing compound 1 in example 1, except that dibenzo [ b, d ] thiophen-1-ylboronic acid was used instead of dibenzo [ b, d ] furan-4-ylboronic acid.
MS：[M+H] + ＝723
Example 9: production of Compound 9
Compound 1B (20.0 g,34.8 mmol) and dibenzo [ B, d ] were reacted under nitrogen atmosphere]Furan-4-ylboronic acid (11.1 g,52.3 mmol) was added to the bis (O-L)
In alkane (200 mL), stir and reflux. Then, potassium carbonate (14.4 g,104.5 mmol) was dissolved in water (60 mL) and added thereto, followed by stirring thoroughly, and bis (tri-t-butylphosphine) palladium (0) (0.5 g,1.0 mmol) was added thereto. After 2 hours of reaction, the temperature was lowered to room temperature and filtered. After the filtrate was extracted with chloroform and water, the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, and then recrystallized using a mixed solution of tetrahydrofuran and ethyl acetate. To be generatedThe solid was filtered and dried to produce compound 9 (16.2 g, yield 66%).
MS：[M+H] + ＝707
Example 10: production of Compound 10
The above-mentioned compound 10 (9.3 g, 38%) was produced by the same method as the method for producing compound 9 in example 9, except that dibenzo [ b, d ] furan-3-ylboronic acid was used instead of dibenzo [ b, d ] furan-4-ylboronic acid.
MS：[M+H] + ＝707
Example 11: production of Compound 11
The above-mentioned compound 11 (14.8 g, 60%) was produced by the same method as the method for producing compound 9 in example 9, except that dibenzo [ b, d ] furan-1-ylboronic acid was used instead of dibenzo [ b, d ] furan-4-ylboronic acid.
MS：[M+H] + ＝707
Example 12: production of Compound 12
The above-mentioned compound 12 (17.4 g, 69%) was produced by the same method as the method for producing compound 9 in example 9, except that dibenzo [ b, d ] thiophen-4-ylboronic acid was used instead of dibenzo [ b, d ] furan-4-ylboronic acid.
Example 13: production of Compound 13
Compound 1C (20.0 g,34.8 mmol) and dibenzo [ b, d ] were reacted under nitrogen atmosphere]Furan-4-ylboronic acid (11.1 g,52.3 mmol) was added to the bis (O-L)
In alkane (200 mL), stir and reflux. Then, potassium carbonate (14.4 g,104.5 mmol) was dissolved in water (60 mL) and then stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.5 g,1.0 mmol) was added thereto. After 2 hours of reaction, the temperature was lowered to room temperature and filtered. After the filtrate was extracted with chloroform and water, the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, and then recrystallized using a mixed solution of tetrahydrofuran and ethyl acetate. The resultant solid was filtered and dried, whereby compound 13 was produced (17.2 g, yield 70%).
MS：[M+H] + ＝707
Example 14: production of Compound 14
The above-mentioned compound 14 (16.2 g, 66%) was produced by the same method as the method for producing compound 13 in example 13, except that dibenzo [ b, d ] furan-3-ylboronic acid was used instead of dibenzo [ b, d ] furan-4-ylboronic acid.
MS：[M+H] + ＝707
Example 15: production of Compound 15
The above-mentioned compound 15 (5.9 g, 24%) was produced by the same method as the method for producing compound 13 in example 13, except that dibenzo [ b, d ] furan-1-ylboronic acid was used instead of dibenzo [ b, d ] furan-4-ylboronic acid.
Example 16: production of Compound 16
The above-mentioned compound 16 (4.7 g, 19%) was produced by the same method as the method for producing compound 13 in example 13, except that dibenzo [ b, d ] thiophen-4-ylboronic acid was used instead of dibenzo [ b, d ] furan-4-ylboronic acid.
Experimental example 1
To ITO (indium tin oxide)
The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following HI-1 compound was used
And performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, the following HT-1 compound was used as a catalyst>
Forming a hole transport layer by thermal vacuum vapor deposition, wherein the HT-2 compound is added to the hole transport layer>
And vacuum evaporation is performed to form an electron blocking layer. On the electron blocking layer, as a light emitting layer, the above-mentioned solid state light emitting layer is formedThe compound 1 produced in example 1, the YGH-1 compound described below, and the phosphorescent dopant YGD-1 were co-evaporated at a weight ratio of 44:44:12 to form
A light emitting layer of thickness. On the above luminescent layer, the following ET-1 compound was used as +.>
An electron transport layer is formed by vacuum vapor deposition, and the following ET-2 compound and Li are formed on the electron transport layer by vacuum vapor deposition at a weight of 98:2>
An electron injection layer of thickness. On the electron injection layer, aluminum is added with +.>
The thickness was evaporated to form a cathode. />
In the above process, the vapor deposition rate of the organic matter is maintained
Aluminum maintenance>
Vapor deposition rate per sec, vacuum degree was maintained at 1×10 during vapor deposition -7 ～5×10 -8 And (5) a bracket.
Experimental examples 2 to 16
An organic light emitting device was manufactured in the same manner as in experimental example 1 above, except that the compound 1 described in table 1 below was used instead of the compound 1 of example 1 in experimental example 1 above.
Comparative examples 1 to 5
An organic light emitting device was manufactured in the same manner as in experimental example 1 above, except that the compound 1 described in table 1 below was used instead of the compound 1 of example 1 above.
The compounds of CE1 to CE5 of table 1 below are shown below.
In the above experimental examples and comparative experimental examples, the organic light emitting device was used at 10mA/cm 2 Voltage and efficiency were measured at a current density of 50mA/cm 2 The lifetime was measured at the current density of (2), and the results are shown in table 1 below. At this time, LT 95 Refers to the time required to reach 95% relative to the initial brightness.
[ Table 1]
As shown in table 1 above, it was confirmed that when the compound of the present invention was used as a light-emitting layer substance, the compound exhibited characteristics of low voltage, excellent efficiency, and excellent lifetime, as compared with comparative examples 1 to 5. It is thus predicted that in the compound of the present invention, 2 triazine units affect each other by being located in the ortho position (ortho) to the phenyl group, and that the stability of an electron transporting unit and a substance is excellent by directly or indirectly substituting 1 or more triazine units with dibenzofuran or thiophene, and further that the voltage of the device is low, the efficiency, the lifetime, and the like are excellent.
[ symbolic description ]
1: substrate 2: anode
3: light emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron blocking layer 8: electron transport layer
9: an electron injection layer.
Claims (12)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
X 1 to X 3 Each independently is N or CR 2 ，X 1 To X 3 More than 1 of them is N,
Y 1 to Y 3 Each independently is N or CR 3 ，Y 1 To Y 3 More than 1 of them is N,
q is O or S, and the total number of the components is O or S,
Ar 1 to Ar 5 Each independently is C 6-60 An aryl group,
L 1 to L 4 Each independently is a single bond; or C 6-60 An arylene group,
R 1 to R 3 Each independently is hydrogen; deuterium; halogen; cyano group; a nitro group; or an amino group,
n1 is an integer of 0 to 4,
n2 is an integer of 0 to 3,
n3 is an integer from 0 to 4.
2. The compound of claim 1, wherein Ar 1 To Ar 3 Each independently is C 6-30 Aryl groups.
3. The compound of claim 1, wherein Ar 1 To Ar 3 Is phenyl.
4. The compound of claim 1, wherein L 1 To L 3 Each independently is a single bond, or C 6-30 Arylene groups.
5. The compound of claim 1, wherein L 1 To L 3 Is a single bond.
6. The compound according to claim 1, wherein the chemical formula 1 is any one of the following chemical formulas 2 to 5:
chemical formula 2
Chemical formula 3
Chemical formula 4
Chemical formula 5
In the chemical formulas 2 to 5, for X 1 To X 3 、Y 1 To Y 3 、Q、L 4 、Ar 4 、Ar 5 The description of n2 and n3 is the same as defined in claim 1.
7. The compound of claim 1, wherein Ar 4 And Ar is a group 5 Each independently is C 6-30 Aryl groups.
8. The compound of claim 1, wherein L 4 Is a single bond, phenylene, biphenyldiyl, or naphthylene.
9. The compound of claim 1, wherein the compound is any one selected from the group consisting of:
10. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 9.
11. An organic light-emitting device according to claim 10 wherein the organic layer may comprise a light-emitting layer comprising more than 2 host species.
12. The organic light-emitting device according to claim 11, wherein the 2 or more host substances include a compound represented by the chemical formula 1.
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