CN113039183B - Novel compound and organic light emitting device comprising the same - Google Patents

Novel compound and organic light emitting device comprising the same Download PDF

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CN113039183B
CN113039183B CN202080006172.3A CN202080006172A CN113039183B CN 113039183 B CN113039183 B CN 113039183B CN 202080006172 A CN202080006172 A CN 202080006172A CN 113039183 B CN113039183 B CN 113039183B
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compound
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light emitting
organic
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CN113039183A (en
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韩修进
李东勋
张焚在
徐尚德
郑珉祐
李征夏
朴瑟灿
黄晟现
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LG Chem Ltd
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Abstract

The present invention provides novel compounds and organic light emitting devices comprising the same.

Description

Novel compound and organic light emitting device comprising the same
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2019-0077251 at 27 in 6 months and korean patent application No. 10-2020-0069692 at 9 in 6 months in 2020, the entire contents of the disclosures of the korean patent application are incorporated as part of the present specification.
The present invention relates to novel compounds and organic light emitting devices comprising 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 into the organic layer from the anode, electrons are injected into the organic layer from the cathode, 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 1) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention relates to a novel organic light emitting material 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,
l is connected with carbon number 1, carbon number 2 or carbon number 3,
l is a single bond, or substituted or unsubstituted C 6-60 An arylene group,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-60 A heteroaryl group, which is a group,
R 1 each independently is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-60 A heteroaryl group, which is a group,
R 2 each independently is a substituted or unsubstituted C 6-60 Aryl, benzofuranyl, benzothienyl, dibenzofuranyl or phenylbenzothienyl,
p is an integer of 0 to 5,
q is an integer from 1 to 8.
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 may be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, low driving voltage, and/or improvement of lifetime characteristics may be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.
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, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10, 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,or->Represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; a nitrile 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 (Alkyl thio); arylthio (Aryl thio); alkylsulfonyl (Alkyl sulfoxy); 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, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as 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 group 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 group may be a group 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 group 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, or triphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like, A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above fluorenyl group is substituted, it may beEtc. However, the present invention 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. According to one embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to one embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,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-mentioned 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 above-mentioned examples of the alkyl group. 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 examples of alkenyl groups described above. 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 thereto. In this specification, the heteroaryl group is not a 1-valent group, but a combination of 2 substituents, and the above description of the heteroaryl group can be applied.
Preferably, the above chemical formula 1 may be represented by the following chemical formulas 1-1 to 1-3:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
In the above chemical formulas 1-1 to 1-3,
for L, ar 1 、Ar 2 、R 1 、R 2 The descriptions of p and q are the same as those of the above chemical formula 1.
Preferably, L may be a single bond, or a substituted or unsubstituted C 6-20 An arylene group,
more preferably, L may be a single bond, phenylene or naphthylene.
Preferably Ar 1 And Ar is a group 2 May each independently be substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-20 A heteroaryl group, which is a group,
more preferably Ar 1 And Ar is a group 2 Can each independently be phenyl, biphenyl, naphthyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, phenyl substituted with 5 deuterium, carbazolylphenyl or phenylbenzothiophenyl,
most preferably Ar 1 And Ar is a group 2 May each independently be any one selected from the group consisting of:
preferably, R 1 May each independently be hydrogen; deuterium; substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstitutedGeneration C containing any one or more selected from N, O and S 2-20 A heteroaryl group, which is a group,
more preferably, R 1 May each independently be hydrogen, deuterium, phenyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl.
Preferably, R 2 May each independently be substituted or unsubstituted C 6-20 Aryl, benzofuranyl, benzothienyl, dibenzofuranyl or phenylbenzothienyl,
more preferably, R 2 May each independently be any one selected from the group consisting of:
preferably, q may be 1 or 2.
Representative examples of the compounds represented by the above chemical formula 1 are shown below:
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as an example, the compound represented by the above chemical formula 1 may be produced by a production method shown in the following chemical formula 1, and other compounds may be produced by a similar method.
[ reaction type 1]
In the above reaction scheme 1, L, ar 1 、Ar 2 、R 1 、R 2 P and q are as defined in formula 1 above, X 1 And X 2 Each independently is halogen, X 1 And X 2 Preferably fluorine, chlorine or bromine.
Step 1 of the above reaction formula 1 is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used for the suzuki coupling reaction can be changed according to a technique known in the art. In addition, the step 2 of the above reaction formula 1 is preferably carried out in the presence of a palladium catalyst and a base as an amine substitution reaction, and the reactive group used for the amine substitution reaction can be changed according to a technique 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, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as the organic layer, but the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
The organic layer may include a light-emitting layer, and the light-emitting layer may include a compound represented by chemical formula 1. In particular, the compounds according to the invention can be used as hosts for light-emitting layers.
The organic layer may include a hole transporting layer, a hole injecting layer, or a layer that performs hole transport and hole injection at the same time, and the hole transporting layer, the hole injecting layer, or the layer that performs hole transport and hole injection at the same time may include a compound represented by chemical formula 1.
In addition, the electron transport layer, the electron injection layer, or the layer performing both electron transport and electron injection may contain a compound represented by the above chemical formula 1.
The organic layer may include a light-emitting layer and a hole-transporting layer, and the light-emitting layer or the hole-transporting layer may include a compound represented by chemical formula 1.
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, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10, 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, light emitting layer, and electron transport layer.
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, when 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. At this time, it 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 may 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 of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methyl) Thiophene), 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 a hole-transporting substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer is preferable, and 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 above-described electron blocking layer is a layer for preventing electrons injected from the cathode from being recombined in the light emitting layer but transferred to the hole transporting layer, thereby being interposed between the hole transporting layer and the light emitting layer, and is also referred to as an electron blocking layer. In the electron blocking layer, a substance having a smaller electron affinity than the electron transporting layer is preferably used.
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 is preferably a substance having 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, and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material. Examples of the host material include aromatic condensed ring derivatives and heterocyclic compounds. 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, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Preferably, a compound represented by the above chemical formula 1 may be included as a host material.
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, etc., a styrylamine compound in which at least 1 arylvinyl group is substituted in a substituted or unsubstituted arylamine, substituted or unsubstituted with 1 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl and arylamino groups And (3) replacing. 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 hole blocking layer is a layer which is interposed between the electron transport layer and the light emitting layer to prevent holes injected from the anode from being recombined in the light emitting layer and transferred to the electron transport layer, and is also referred to as a hole suppressing layer. A substance having a large ionization energy is preferably used for the hole blocking layer.
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 those having a low work function accompanied by an aluminum layer or a silver layer. Specifically 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, fluorenylmethenes, anthrones, and the like, and derivatives thereofExamples of the nitrogen-containing five-membered ring include, but are not limited to, an aromatic hydrocarbon, a metal complex, and a nitrogen-containing five-membered ring derivative.
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 the 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 illustrated in the following examples. However, the following examples are given for the purpose of illustrating the present invention, and the scope of the present invention is not limited thereto.
Production example 1: production of Compound 1
Step 1) production of Compound 1-a
2-bromo-4-chloro-1-fluorobenzene (50 g,238.7 mmol) and phenylboronic acid (29.1 g,238.7 mmol) were added to 1000ml of tetrahydrofuran under nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (99 g,716.2 mmol) was dissolved in 99ml of water and charged, and tetrakis (triphenylphosphine) palladium (8.3 g,7.2 mmol) was charged after stirring thoroughly. After 2 hours of reaction, the mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was again put into 987ml of chloroform 20 times and dissolved, after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, After stirring, filtration was carried out, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to thereby prepare white solid compound 1-a (34.5 g,70%, MS: [ M+H] + ＝207.6)。
Step 2) production of Compound 1-b
Compound 1-a (30 g,145.2 mmol) and bis (pinacolato) diboron (36.9 g,145.2 mmol) are added to 600ml of diboron under a nitrogen atmosphereIn an alkane (Diox), stirring and refluxing. Then, potassium acetate (92.5 g,435.5 mmol) was added, and after stirring thoroughly, pd (dba) was added 2 (2.5 g,4.4 mmol) and tricyclohexylphosphine (2.4 g,8.7 mmol). After 3 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The obtained product was again poured into 10 times 433ml of chloroform and dissolved, after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to thereby prepare white solid compound 1-b (34.2 g,79%, MS: [ M+H)] + ＝299.2)。
Step 3) production of Compound 1-c
Compound 1-b (50 g,167.7 mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (44.9 g,167.7 mmol) were added to 1000ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (69.5 g,503.1 mmol) was dissolved in 70ml of water and charged, and tetrakis (triphenylphosphine) palladium (5.8 g,5 mmol) was charged after stirring thoroughly. After 3 hours of reaction, the mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting product was again taken up in 20 times 1353ml of chloroform and dissolved, with water After washing 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol, thereby obtaining white solid compound 1-c (47.4 g,70%, MS: [ M+H] + ＝404.5)。
Step 4) production of Compound 1
Compound 1-c (20 g,43.4 mmol) and 3-phenyl-9H-carbazole (10.6 g,43.4 mmol) were added to 400ml of dimethylformamide under nitrogen, stirred and refluxed. Then, cesium carbonate (42.4 g,130.3 mmol) was charged, heated and stirred. After 3 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was poured into 817ml of chloroform and dissolved, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, the filtrate was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate, whereby yellow solid compound 1 (20.1 g,74%, MS: [ M+H) was produced] + ＝627.8)。
Production example 2: production of Compound 2
In production example 1, compound 2 was produced by the same production method as that of compound 1, except that (phenyl-d 5) boric acid was used instead of phenylboric acid. (MS: [ M+H ]] + ＝632.3)。
Production example 3: production of Compound 3
Compound 3 was produced by the same production method as that of compound 1, except that 4- (phenyl-d 5) -9H-carbazole was used instead of 3-phenyl-9H-carbazole in production example 1. (MS [ M+H)] + ＝632)。
Production example 4: production of Compound 4
In production example 1, 4- (dibenzo [ b, d) was used]Compound 4 was produced by the same production method as that of compound 1, except that furan-2-yl) -9H-carbazole was used instead of 3-phenyl-9H-carbazole. (MS [ M+H)] + ＝717)。
Production example 5: production of Compound 5
In production example 1, compound 5 was produced by the same production method as that of compound 1, except that 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 2-phenyl-9H-carbazole were used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 3-phenyl-9H-carbazole. (MS [ M+H)] + ＝716)。
Production example 6: production of Compound 6
In production example 1, 2-chloro-4- (dibenzo [ b, d) was used]Compound 6 was produced by the same production method as that of compound 1, except that thiophen-4-yl) -6-phenyl-1, 3, 5-triazine and 4-phenyl-9H-carbazole were used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 3-phenyl-9H-carbazole. (MS [ M+H)] + ＝733)。
Production example 7: production of Compound 7
In production example 1, 2-chloro-4- (dibenzo [ b, d) was used ]Furan-4-yl) -6- (dibenzo [ b, d)]Thiophen-4-yl) -1,3, 5-triazines instead of 2-chloro-4, 6-diphenyl-1, 3, 5-trisExcept for the oxazine, compound 7 was produced by the same production method as that of compound 1. (MS [ M+H)] + ＝823)。
Production example 8: production of Compound 8
In production example 1, compound 8 was produced by the same production method as that of compound 1, except that (3- (9H-carbazol-9-yl) phenyl) boric acid was used instead of phenylboric acid. (MS [ M+H)] + ＝792)。
Production example 9: production of Compound 9
In production example 1, compound 9 was produced by the same production method as that of compound 1, except that 2- (3-chlorophenyl) -4, 6-diphenyl-1, 3, 5-triazine and 4-phenyl-9H-carbazole were used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 3-phenyl-9H-carbazole. (MS [ M+H)] + ＝703)。
Production example 10: production of Compound 10
In production example 1, 2- (3-chlorophenyl) -4, 6-diphenyl-1, 3, 5-triazine and 2- (9H-carbazol-4-yl) benzo [ d ] were used]Compound 10 was produced by the same production method as that of compound 1, except that thiazole was used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 3-phenyl-9H-carbazole. (MS [ M+H)] + ＝760)。
Production example 11: production of Compound 11
Step 1) production of Compound 11-a
1-bromo-4-chloro-2-fluorobenzene (50 g,238.7 mmol) and phenylboronic acid (29.1 g,238.7 mmol) were added to 1000ml of tetrahydrofuran under nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (99 g,716.2 mmol) was dissolved in 99ml of water and charged, and tetrakis (triphenylphosphine) palladium (8.3 g,7.2 mmol) was charged after stirring thoroughly. After 1 hour of reaction, the mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was again poured into 987ml of chloroform and dissolved, after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to thereby prepare white solid compound 11-a (30.1 g,61%, MS: [ M+H)] + ＝207.6)。
Step 2) production of Compound 11-b
Compound 11-a (30 g,145.2 mmol) and bis (pinacolato) diboron (36.9 g,145.2 mmol) are added to 600ml of diboron under a nitrogen atmosphereIn alkane, stir and reflux. Then, potassium acetate (92.5 g,435.5 mmol) was added, and Pd (dba) was added with sufficient agitation 2 (2.5 g,4.4 mmol) and tricyclohexylphosphine (2.4 g,8.7 mmol). After the reaction for 6 hours, the reaction mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The obtained product was again poured into 10 times 433ml of chloroform and dissolved, after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to thereby prepare white solid compound 11-b (32 g,74%, MS: [ M+H) ] + ＝299.2)。
Step 3) production of Compound 1-c
11-b (50 g,167.7 mmol) and 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine (45.7 g,167.7 mmol) were added to 1000ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (69.5 g,503.1 mmol) was dissolved in 70ml of water and charged, and tetrakis (triphenylphosphine) palladium (5.8 g,5 mmol) was charged after stirring thoroughly. After 1 hour of reaction, the mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resultant product was again put into 1370ml of chloroform 20 times and dissolved, after washing with water 2 times, an organic layer was separated, anhydrous magnesium sulfate was added, filtration was performed after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to thereby prepare white solid compound 11-c (48.6 g,71%, MS: [ M+H)] + ＝409.5)。
Step 4) production of Compound 11
Compound 11-c (20 g,49 mmol) and 4-phenyl-9H-carbazole (11.9 g,49 mmol) were added to 400ml of dimethylformamide under nitrogen atmosphere, stirred and refluxed. Then, cesium carbonate (47.9 g,146.9 mmol) was charged, heated and stirred. After 3 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was poured into 30 times 928ml of chloroform and dissolved, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate, whereby yellow solid compound 11 (21.7 g,70%, MS: [ M+H) was produced ] + ＝632.8)。
Production example 12: production of Compound 12
In production example 11, 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 2-phenyl-9H-carbazole were used instead of 2-chloro-4-benzeneCompound 12 was produced by the same production method as that of compound 11, except for the group-6- (phenyl-d 5) -1,3, 5-triazine and 4-phenyl-9H-carbazole. (MS [ M+H)] + ＝760)。
Production example 13: production of Compound 13
In production example 11, 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 4- (dibenzo [ b, d) were used]Compound 13 was produced by the same production method as that of compound 11, except that furan-2-yl) -9H-carbazole was used instead of 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine and 4-phenyl-9H-carbazole. (MS [ M+H)] + ＝717)。
Production example 14: production of Compound 14
In production example 11, 2- (3-chlorophenyl) -4- (dibenzo [ b, d) was used]Compound 14 was produced by the same production method as that of compound 11, except that thiophen-4-yl) -6-phenyl-1, 3, 5-triazine was used instead of 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine. (MS [ M+H)] + ＝809)。
Production example 15: production of Compound 15
In production example 11, compound 15 was produced by the same production method as that of compound 11, except that 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 3, 6-diphenyl-9H-carbazole were used instead of 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine and 4-phenyl-9H-carbazole. (MS [ M+H) ] + ＝703)。
Production example 16: production of Compound 16
Step 1) production of Compound 16-a
2-bromo-1-chloro-3-fluorobenzene (50 g,238.7 mmol) and phenylboronic acid (29.1 g,238.7 mmol) were added to 1000ml of tetrahydrofuran under nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (99 g,716.2 mmol) was dissolved in 99ml of water and charged, and tetrakis (triphenylphosphine) palladium (8.3 g,7.2 mmol) was charged after stirring thoroughly. After 3 hours of reaction, the mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was again poured into 987ml of chloroform and dissolved, after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to thereby prepare 16-a (29.6 g,60% MS: [ M+H) as a white solid compound] + ＝207.6)。
Step 2) production of Compound 16-b
Compound 16-a (30 g,145.2 mmol) and bis (pinacolato) diboron (36.9 g,145.2 mmol) are added to 600ml of diboron under a nitrogen atmosphereIn alkane, stir and reflux. Then, potassium acetate (92.5 g,435.5 mmol) was added, and after stirring thoroughly, pd (dba) was added 2 (2.5 g,4.4 mmol) and tricyclohexylphosphine (2.4 g,8.7 mmol). After 7 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The obtained product was again poured into 10 times 433ml of chloroform and dissolved, after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to thereby prepare white solid compound 16-b (33.3 g,77%, MS: [ M+H) ] + ＝299.2)。
Step 3) production of Compound 1-c
Compound 16-b (50 g,167.7 mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (44.9 g,167.7 mmol) were added to 1000ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (69.5 g,503.1 mmol) was dissolved in 70ml of water and charged, and after stirring well, tetrakis (triphenylphosphine) palladium (5.8 g,5 mmol) was charged. After 2 hours of reaction, the mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was again poured into 20 times 1353ml of chloroform and dissolved, after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to thereby prepare white solid compound 16-c (52.1 g,77%, MS: [ M+H)] + ＝404.5)。
Step 4) production of Compound 16
Compound 16-c (20 g,49.6 mmol) and 2-phenyl-9H-carbazole (12.1 g,49.6 mmol) were added to 400ml of dimethylformamide under nitrogen, stirred and refluxed. Then, cesium carbonate (48.5 g,148.7 mmol) was charged, heated and stirred. After 3 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was poured into 932ml of chloroform 30 times and dissolved, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate, whereby yellow solid compound 16 (23 g,74%, MS: [ M+H) was produced ] + ＝627.8)。
Production example 17: production of Compound 17
In production example 16, 2-chloro-4- (dibenzo [ b, d) was used]Compound 17 was produced by the same production method as that of compound 16, except that thiophen-4-yl) -6-phenyl-1, 3, 5-triazine and 4-phenyl-9H-carbazole were used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 2-phenyl-9H-carbazole. (MS [ M+H)] + ＝733)。
Production example 18: production of Compound 18
In preparation example 16, compound 18 was produced by the same production method as that of compound 16, except that 2- (3-chlorophenyl) -4, 6-diphenyl-1, 3, 5-triazine and 3-phenyl-9H-carbazole were used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 2-phenyl-9H-carbazole. (MS [ M+H)] + ＝703)。
Production example 19: production of Compound 19
Compound 19 was produced by the same production method as that of compound 16, except that 4- (phenyl-d 5) -9H-carbazole was used instead of 2-phenyl-9H-carbazole in production example 16. (MS [ M+H)] + ＝632)。
Production example 20: production of Compound 20
In production example 16, a (4- (dibenzo [ b, d)]Thiophene-4-yl) phenyl) boronic acid, 2- (4-chlorophenyl) -4, 6-diphenyl-1, 3, 5-triazine, and 4-phenyl-9H-carbazole were produced by the same production method as that of compound 16, except that phenylboronic acid, 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, and 2-phenyl-9H-carbazole were replaced. (MS [ M+H) ] + ＝885)。
Example 1
ITO (Indium Tin Oxide) toThe 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 compound HT-A and the following compound PD were combined in a weight ratio of 95:5Is subjected to thermal vacuum evaporation, and then, only the following compound HT-A is added +.>And vapor deposition is performed to form a hole transport layer. On the hole transport layer, the following compound HT-B was used as +.>And performing thermal vacuum evaporation to form an electron blocking layer. On the above electron blocking layer, the above-produced compound 1 and the following compound GD were combined in a weight ratio of 85:15 +. >And vacuum vapor deposition is performed to the thickness of the substrate to form a light-emitting layer. On the above luminescent layer, the following compound ET-A was used as +.>Vacuum deposition is performed to form a hole blocking layer. On the hole blocking layer, the following is combinedThe weight ratio of the compound ET-B to the following compound Liq is 2:1 and +.>Is subjected to thermal vacuum evaporation, and then LiF and magnesium are added in a weight ratio of 1:1 +.>And vacuum evaporating to form electron transporting and injecting layer. On the above electron injection layer, magnesium and silver are added in a weight ratio of 1:4 and +.>And vapor deposition is performed to form a cathode, thereby manufacturing an organic light-emitting device.
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathodeVapor deposition rate of silver and magnesium is maintained->Is to maintain a vacuum degree of 2 x 10 during vapor deposition -7 To 5 x 10 -6 The support, thereby manufacturing the organic light emitting device.
Examples 2 to 25 and comparative examples 1 to 11
An organic light emitting device was manufactured in the same manner as in example 1, except that the compound described in table 1 below was used instead of the compound 1 in example 1.
For reference, in examples 21 to 25 and comparative examples 9 to 11, the compounds described in the following table 1 were used in a weight ratio of 1:1 instead of the compound 1, thereby producing organic light emitting devices. Example 21 by way of example, in example 1, compound 2 and compound H-2 were used in a weight ratio of 1:1 instead of compound 1. In Table 1 below, compounds H-2, C1 to C8 are shown below, respectively.
Experimental example
The voltage, efficiency, and lifetime (T95) were measured by applying a current to the organic light emitting devices manufactured in the above examples and comparative examples, and the results are shown in table 1 below. At this time, the voltage and the efficiency were such that 10mA/cm was applied 2 Is measured by the current density of the sample. T95 in Table 1 below means that the current density was 20mA/cm 2 The time measured when the initial brightness was reduced to 95%.
TABLE 1
/>
In the compound according to the present invention, aryl groups are substituted in the ortho-position of carbazole, and thus structural warpage occurs, and thus charge transfer (charge transfer) cannot be well achieved. Therefore, it is presumed that the stability of the molecule is high, and the molecule is advantageous for both hole and electron transport. In addition, the precursor of chemical formula 1 of the present invention is further substituted with various aryl and heteroaryl groups, so that the electron transport characteristics can be variously adjusted, and thus it is predicted that it is advantageous to coordinate charge balance according to the change of the general layer.
In table 1 above, examples 1 to 20 and comparative examples 1 to 8 are examples of organic light-emitting devices using a host alone in a light-emitting layer, and examples 21 to 25 and comparative examples 9 to 11 are device examples using 2 hosts in a light-emitting layer. It was confirmed that the organic light emitting device of the example using the compound of the present invention was higher in efficiency and lower in driving voltage than the organic light emitting device of the comparative example, and particularly, the life characteristics were greatly improved in the case of using not only 1 type of host but also 2 types of host in the light emitting layer.
Therefore, as shown in table 1 above, it was confirmed that the compound of chemical formula 1, when used as a host of an organic light-emitting device, exhibited characteristics of low voltage, high efficiency, and long life.
Symbol 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: hole blocking layer
9: electron transport layer 10: an electron injection layer.

Claims (4)

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,
l is connected with carbon number 2 or carbon number 3,
l is a single bond, phenylene or naphthylene,
Ar 1 and Ar is a group 2 Each independently is phenyl, biphenyl, naphthyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, or phenyl substituted with 5 deuterium,
R 1 each independently of the other is hydrogen or deuterium,
R 2 each independently is any one selected from the following groups:
p is an integer of 0 to 5,
q is an integer from 1 to 8.
2. The compound of claim l, wherein q is 1 or 2.
3. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:
/>
/>
4. 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 3.
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