CN111138395A - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
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- CN111138395A CN111138395A CN201911065499.3A CN201911065499A CN111138395A CN 111138395 A CN111138395 A CN 111138395A CN 201911065499 A CN201911065499 A CN 201911065499A CN 111138395 A CN111138395 A CN 111138395A
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- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention relates to a novel compound and an organic light emitting device including the same, and the novel compound according to an embodiment of the present invention is suitable for an organic light emitting device and can ensure high efficiency, long life, low driving voltage, and driving stability of the organic light emitting device.
Description
Technical Field
The present invention relates to a novel compound and an organic light emitting device comprising the same.
Background
In the organic light emitting diode, materials used as the organic layer may be broadly classified into a light emitting material, a hole injecting material, a hole transporting material, an electron injecting material, and the like according to functions. The light-emitting materials may be classified into high-molecular and low-molecular materials according to molecular weight, fluorescent materials in a singlet excited state derived from electrons and phosphorescent materials in a triplet excited state derived from electrons according to a light-emitting mechanism, and blue, green and red light-emitting materials and yellow and orange light-emitting materials required for embodying a better natural color may be classified according to light emission colors. Also, in order to increase color purity and increase luminous efficiency by energy transfer, a host/dopant species may be used as a light emitting substance. The principle is that when a small amount of a dopant having a smaller energy band gap and excellent light emission efficiency than a host mainly constituting a light emitting layer is mixed in an auxiliary layer, excitons generated in the host are transported to the dopant, and light with high efficiency is emitted. In this case, since the wavelength of the host is shifted to the wavelength band of the dopant, light having a desired wavelength can be obtained according to the type of the dopant and the host used.
Many compounds have been known as materials used in such organic light emitting devices, but in the case of organic light emitting devices using the materials known so far, development of new materials is continuously required due to high driving voltage, low efficiency and short lifetime. Accordingly, efforts are continuously made to develop an organic light emitting device having low voltage driving, high luminance, and long life using a substance having excellent characteristics.
Documents of the prior art
Patent document
Korean laid-open patent No. 10-2015-0086721
Disclosure of Invention
The present invention provides a novel organic compound and an organic light emitting device including the same.
However, the problems to be solved by the present invention are not limited to the above-described problems, and other problems not described may be clearly understood by those skilled in the art from the following description.
A first embodiment of the present invention provides a compound represented by the following chemical formula 1:
chemical formula 1
In the above-described chemical formula 1,
x is O or S, and X is O or S,
Ar1to Ar3Each independently is substituted or unsubstituted C6～C50But, not fluorene,
R1to R2Each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Or a substituted or unsubstituted C6～C30Can be at a plurality of adjacent R1R is2With or without the formation of a ring therebetween,
R3to R4Each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Or a substituted or unsubstituted C6～C50The aryl group of (a) is,
l and n are each independently 0 or an integer of 1 to 3, and m is 0 or an integer of 1 to 4.
A second embodiment of the present invention provides an organic light-emitting device including an organic layer containing the compound of the present invention between a first electrode and a second electrode.
A diarylamine compound according to an example of the present invention has dibenzothiophene or dibenzofuran as a substituent, and two nitrogens are linked to meta (1, 3-phenylene) or ortho (1, 2-phenylene) through phenylene groups to form the Highest Occupied Molecular Orbital (HOMO) level suitable for a light-emitting auxiliary layer, whereby a low-voltage organic light-emitting device can be realized.
Also, two nitrogens are linked to meta (1, 3-phenylene) or ortho (1, 2-phenylene) through phenylene, and a heterocyclic structure such as dibenzothiophene or dibenzofuran substituent is minimized, a high Lowest Unoccupied Molecular Orbital (LUMO) energy level is formed, and a high T1 is maintained, thereby maximizing electron and exciton blocking effects.
Further, by introducing 1 dibenzothiophene or dibenzofuran substituent into a structure directly bonded to nitrogen, the bulky property of the molecule is minimized, the molecular arrangement is facilitated, the Hole Mobility (Hole Mobility) is improved, and the roll-off phenomenon is suppressed, thereby realizing a long-life organic light emitting device.
In addition, the diarylamine compound has an apolar aryl group, and maintains a deep HOMO level at which holes are easily injected into the light-emitting layer, thereby realizing a high-efficiency organic light-emitting device.
Further, the diarylamine compound has an aryl group with excellent thermal stability, and stability is secured in a deposition process and device driving, whereby a long-life organic light-emitting device can be realized.
Drawings
Fig. 1 shows a schematic view of an organic light emitting device according to an embodiment of the present invention.
Description of reference numerals
100: substrate
200: hole injection layer
300: hole transport layer
400: luminescent layer
500: electron transport layer
600: electron injection layer
1000: a first electrode
2000: second electrode
Detailed Description
Examples and embodiments of the present invention are described in detail below with reference to the accompanying drawings so that those skilled in the art can easily implement the invention.
However, the present invention can be realized in various forms and is not limited to the examples and embodiments described herein. In the drawings, for the purpose of clearly explaining the present invention, portions not related to the explanation are omitted, and like reference numerals are given to like portions throughout the specification.
Throughout the present specification, when an element is "on" another element, it includes not only the case where the element is in contact with the other element, but also the case where the other element is present between the two elements.
Throughout the present specification, when a portion "includes" a structural element, it is meant that other structural elements may be included, but not excluded, unless otherwise stated. The terms "about," "substantially," and the like, as used throughout the specification are used in the sense of their numbers or close to their numbers to indicate inherent preparation and material tolerances, so as to prevent an assiduous intruder from inadvertently making use of the disclosure in which exact or absolute numbers are mentioned to assist in understanding the invention.
Throughout the present specification, the term "combination thereof" contained in an expression of Markush (Markush) means a mixture or combination of one or more kinds selected from the group consisting of a plurality of structural elements described in an expression of Markush, and means including one or more kinds selected from the group consisting of the plurality of structural elements.
Throughout the present specification, the expression "A and/or B" means "A or B, or A and B".
Throughout the present specification, the term "aryl" is meant to encompass C5-30The aromatic hydrocarbon ring group of (2), for example, phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthryl, triphenylalkenyl, phenylalkenyl,
Fluoranthenyl, benzofluorenyl, benzotrichenyl, benzotriphenylenyl, benzo
An aromatic ring such as a phenyl group, an anthracenyl group, a stilbene group, or a pyrenyl group, and a "heteroaryl group" is a group containing at least one hetero element C3-30The aromatic ring of (a) is meant to include, for example, a heterocyclic group formed from pyrrolinyl, pyrazinyl, pyridyl, indolyl, isoindolyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, benzothienyl, dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthryl cry yl, acridinyl, phenanthrolinyl, thienyl, and a heterocyclic group formed from a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, an indole ring, a quinoline ring, an acridine ring, a pyrrolidine ring, a dioxane ring, a piperidine ring, a morpholine ring, a piperazine ring, a carbazole ring, a furan ring, a thiophene ring, an oxazole ring, an oxadiazole ring, a benzoxazole ring, a thiazole ring, a thiadiazole ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring, or a dibenzothiophene ring.
Throughout the present specification, the term "substituted or unsubstituted" may be meant to be selected from the group consisting of deuterium, halogen, amino, nitrile, nitro or C1～C20Alkyl of (C)2～C20Alkenyl of, C1～C20Alkoxy group of (C)3～C20Cycloalkyl of, C3～C20Heterocycloalkyl of (A), C6～C30Aryl and C3～C30One or more groups of the group consisting of heteroaryl groups of (a) are substituted or unsubstituted.
In addition, throughout the present specification, the same reference numerals may have the same meaning unless otherwise specified.
Throughout the description of the present invention, the term "fluorene" may comprise C substituted or unsubstituted by a hydrogen bonded to the carbon at position 91-20Alkyl, substituted or unsubstituted C5-30Aryl of (2), or substituted or unsubstituted C3-30And (3) heteroaryl substituted.
A first embodiment of the present invention provides a compound represented by the following chemical formula 1.
Chemical formula 1
In the above-described chemical formula 1,
x is O or S, and X is O or S,
Ar1to Ar3Each independently is substituted or unsubstituted C6～C50But, not fluorene,
R1to R2Each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Or a substituted or unsubstituted C6～C30Can be at a plurality of adjacent R1R is2With or without the formation of a ring therebetween,
R3to R4Each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Or a substituted or unsubstituted C6～C30The aryl group of (a) is,
l and n are each independently 0 or an integer of 1 to 3, and m is 0 or an integer of 1 to 4.
A diarylamine compound according to an example of the present invention has dibenzothiophene or dibenzofuran as a substituent, and two nitrogens are linked to meta (1, 3-phenylene) or ortho (1, 2-phenylene) through phenylene groups to form the Highest Occupied Molecular Orbital (HOMO) level suitable for a light-emitting auxiliary layer, whereby a low-voltage organic light-emitting device can be realized.
Also, two nitrogens are linked to meta (1, 3-phenylene) or ortho (1, 2-phenylene) through phenylene, and a heterocyclic structure such as dibenzothiophene or dibenzofuran substituent is minimized, a high Lowest Unoccupied Molecular Orbital (LUMO) energy level is formed, and a high T1 is maintained, thereby maximizing electron and exciton blocking effects.
Further, by introducing 1 dibenzothiophene or dibenzofuran substituent into a structure directly bonded to nitrogen, the bulky property of the molecule is minimized, the molecular arrangement is facilitated, the Hole Mobility (Hole Mobility) is improved, and the roll-off phenomenon is suppressed, thereby realizing a long-life organic light emitting device.
In addition, the diarylamine compound has an apolar aryl group, and maintains a deep HOMO level at which holes are easily injected into the light-emitting layer, thereby realizing a high-efficiency organic light-emitting device.
Further, the diarylamine compound has an aryl group with excellent thermal stability, and stability is secured in a deposition process and device driving, whereby a long-life organic light-emitting device can be realized.
In one example of the present invention, the above chemical formula 1 may be represented by the following chemical formula 2.
Chemical formula 2
The compound represented by the above chemical formula 2 is R in the above chemical formula 13In the case of hydrogen, 2 nitrogens are attached to the meta position of the phenylene linker (1, 3-phenylene). In this case, a deep HOMO is present, and thus efficiency can be effectively improved.
In an example of the present invention, the above chemical formula 2 may be represented by the following chemical formula 3 or chemical formula 4.
Chemical formula 3
Chemical formula 4
In the above-mentioned chemical formula 4,
Ar2and Ar3Each independently being a substituted or unsubstituted C other than fluorene6～C50Aryl of (A), however, Ar2And Ar3At least one of them is C14～C50Aryl group of (1).
The compound represented by the above chemical formula 3 is R in the above chemical formula 24In the case of hydrogen, 2 nitrogens are attached to the meta position of the phenylene linker (1, 3-phenylene). In this case, the bulky characteristic between 2 nitrogens is minimized, and thus it may be advantageous to improve the driving voltage.
The compound represented by the above chemical formula 4 is R in the above chemical formula 24Is phenyl, Ar2And Ar3Each independently being a substituted or unsubstituted C other than fluorene6～C50Aryl group of Ar2And Ar3At least one of them is C14～C50Aryl, 2 nitrogens are attached to the meta position of the phenylene linker (1, 3-phenylene). In this case, pi-conjugation between 2 nitrogens is increased, whereby efficiency can be effectively improved.
In one example of the present invention, the above chemical formula 1 may be represented by the following chemical formula 5.
Chemical formula 5
The compound represented by the above chemical formula 5 is R in the above chemical formula 13This is the case for hydrogen, 2 nitrogens attached to the ortho position (1, 2-phenylene) of the phenylene linker. In this case, there is a higher HOMO, and thus, it can be advantageous to improve the driving voltage.
In one example of the present invention, the above chemical formula 5 may be represented by the following chemical formula 6.
Chemical formula 6
The compound represented by the above chemical formula 6 is R in the above chemical formula 54This is the case for hydrogen, 2 nitrogens attached to the ortho position (1, 2-phenylene) of the phenylene linker. In this case, the bulky characteristic between 2 nitrogens is minimized, and thus it may be advantageous to improve the driving voltage.
According to an embodiment of the present invention, in the above chemical formulas 1 to 6, R1And R2Each independently may be hydrogen, deuterium or phenyl. In this case, the bulky characteristic is minimized, whereby the hole fluidity can be effectively improved.
Also, according to an embodiment of the present invention, in the above chemical formula 1, chemical formula 2 and chemical formula 5, R3And R4Each independently may be hydrogen, deuterium, or substituted or unsubstituted C1～C5Alkyl group of (1). In this case, the bulky characteristic is minimized, whereby the hole fluidity can be effectively improved.
According to an embodiment of the present invention, in the chemical formula 1, the chemical formula 2 and the chemical formula 5, the R is4May be a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group, or a substituted or unsubstituted triphenylene group.
According to an example of the present invention, in the above chemical formulas 1 to 6, X may be O. In this case, there is a rapid hole mobility, whereby the driving is effective and the life can be improved.
According to an example of the present invention, in the above chemical formulas 1 to 6, X may be S. In this case, the bond length of the hetero atom becomes long, whereby the efficiency can be effectively improved.
According to an embodiment of the present invention, in the above chemical formulas 1 to 6, Ar1To Ar3Each independently selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene, and combinations thereof. In this case, T1 may be maintained high, thereby effectively blocking unnecessary excitons from moving to an adjacent organic layer.
Also, according to an embodiment of the present invention, in the above chemical formulas 1 to 6, Ar1To Ar3At least one of which may be naphthyl, phenanthrene, terphenyl or triphenylene. In this case, a high Tg can be maintained, whereby stability can be ensured at the time of device driving.
Also, according to an embodiment of the present invention, in the above chemical formulas 1 to 6, Ar1To Ar3At least one of which may be terphenyl or triphenylene. In this case, the thermal stability of the compound can be ensured by a high Td.
According to an embodiment of the present invention, the compound represented by the above chemical formula 1 may be one of the following compounds, but is not limited thereto.
A second embodiment of the present invention provides an organic light-emitting device comprising the compound of the present invention described above. The organic light emitting device described above may include one or more organic layers containing the compound of the present invention between the first electrode and the second electrode.
In an embodiment of the present invention, the organic layer may be a hole injection layer, a hole transport layer, and a light emission auxiliary layer, but is not limited thereto.
In one embodiment of the present invention, the organic layer containing the compound of the present invention may be a light-emitting auxiliary layer disposed between the hole-transporting layer and the light-emitting layer. In the present invention, the light-emission auxiliary layer refers to a layer formed between the hole transport layer and the light-emitting layer, and may also be referred to as a second hole transport layer, a third hole transport layer, or the like, depending on the number of hole transport layers.
Further, when forming an organic layer, the compound of the present invention can be used alone or together with a known compound.
The organic light emitting device according to an embodiment of the present invention may include one or more organic layers, such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL), between a first electrode (anode) and a second electrode (cathode).
For example, the organic light emitting device described above may be prepared according to the structure described in fig. 1. The organic light emitting device may be stacked with a first electrode (hole injection electrode 1000)/hole injection layer 200/hole transport layer 300/light emitting layer 400/electron transport layer 500/electron injection layer 600/second electrode (electron injection electrode 2000) in this order from bottom to top.
In fig. 1, a substrate used for an organic light emitting device may be used as the substrate 100, and in particular, a transparent glass substrate or a bendable plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance may be used.
The hole injection electrode 1000 serves as a first electrode for injecting holes of the organic light emitting device. In order to inject holes, a material having a low work function may be used, and the material may be formed of a transparent material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), or graphene (graphene).
The hole injection layer 200 may be formed by depositing a hole injection layer material on the first electrode by a vacuum deposition method, a spin coating method, a casting method, an LB (Langmuir-Blodgett) method, or the like. In the case of forming the hole injection layer by the above-described vacuum deposition method, the deposition conditions thereof vary depending on the compound used as the material of the hole injection layer 200, the structure and thermal characteristics of the hole injection layer, and the like, but may be generally at a deposition temperature of 50 to 500 ℃, 10 ℃ or the like-8To 10-3Vacuum degree of torr, 0.01 to
A deposition rate of/sec,
The layer thickness range to 5 μm is suitably selected.
Next, a hole transport layer material is deposited on the hole injection layer 200 by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like, thereby forming a hole transport layer 300. In the case of forming the hole transport layer by the above-described vacuum deposition method, the deposition conditions thereof vary depending on the compound used, but in general, it is preferable to select the conditions within the range substantially the same as the conditions for forming the hole injection layer.
The compound of the present invention can be used for the hole transport layer 300, and as described above, the compound of the present invention can be used alone or together with a known compound. In addition, according to an embodiment of the present invention, the hole transport layer 300 may be one or more layers, and may include a hole transport layer formed only of a known material. Also, according to an embodiment of the present invention, a light-emission auxiliary layer may be formed on the hole transport layer 300.
The light-emitting layer 400 can be formed by depositing a light-emitting material on the hole transport layer 300 or the light-emitting auxiliary layer by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like. In the case of forming the light-emitting layer by the above-described vacuum deposition method, the deposition conditions thereof differ depending on the compound used, but in general, it is preferable to select the conditions within the range substantially the same as the conditions for forming the hole injection layer. In addition, the light-emitting layer material may use a known compound as a host or a dopant.
In addition, when the light-emitting layer is used together with a phosphorescent dopant, a hole-inhibiting material (HBL) may be further laminated by a vacuum deposition method or a spin coating method in order to prevent diffusion of triplet excitons or holes into the electron-transporting layer. The hole-inhibiting substance that can be used in this case is not particularly limited, but any substance can be selected from known substances used as hole-inhibiting materials and used. For example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, or the hole-inhibiting materials described in jp 11-329734 a1 a may be mentioned, and Balq (bis (8-hydroxy-2-methylquinoline) -aluminum biphenoxide), phenanthroline (phenanthroline) compounds (e.g., bcp (basocopoline) available from Universal Display (UDC)) and the like can be used as representative examples.
The electron transport layer 500 is formed on the light emitting layer 400 formed as described above, and in this case, the electron transport layer may be formed by a method such as a vacuum deposition method, a spin coating method, or a casting method. The deposition conditions of the electron transport layer vary depending on the compound used, but in general, it is preferable to select the conditions within the range substantially the same as the conditions for forming the hole injection layer.
Thereafter, an electron injection layer material may be deposited on the electron transport layer 500 to form the electron injection layer 600, and at this time, the electron transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like using a conventional electron injection layer material.
The compound of the present invention or the following substances may be used for the hole injection layer 200, the hole transport layer 300, the light-emitting layer 400, and the electron transport layer 500 of the organic light-emitting device, or the compound of the present invention and known substances may be used together.
The second electrode 2000 for injecting electrons is formed on the electron injection layer 600 by a vacuum deposition method, a sputtering method, or the like. As the second electrode, various metals can be used. Specific examples thereof include aluminum, gold, and silver.
The organic light-emitting device of the invention can adopt not only the organic light-emitting device with the structure of the first electrode, the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer, the electron injection layer and the second electrode, but also the structure of the organic light-emitting device with various structures, and one or two intermediate layers can be formed according to the requirement.
As described above, the thickness of each organic layer formed according to the present invention may be adjusted according to a desired degree, specifically, 1 to 1000nm, more specifically, 5 to 200 nm.
In the present invention, the organic layer including the compound represented by chemical formula 1 has an advantage in that the surface is uniform and the morphological stability is excellent because the thickness of the organic layer can be adjusted to a molecular unit.
The organic compound of the present embodiment can be applied to the content described in the first embodiment of the present invention, but is not limited thereto.
Hereinafter, the present invention will be described more specifically with reference to examples, but the scope of the present invention is not limited to these examples.
Examples
Synthesis of Compound represented by chemical formula 1
The compound represented by chemical formula 1 may be synthesized by the following reaction, without being limited thereto.
Synthesis of intermediate IM
For the synthesis of the target compound, the intermediate IM can be synthesized by, but not limited to, the following reaction.
Synthesis of intermediate IM1
Intermediate IM1 was synthesized as follows.
In a round-bottomed flask, 10.0g of 2-bromodibenzo [ b, d ] was charged]Furan, 7.5g of [1,1' -biphenyl ]]-4-amine, 5.8g of t-BuONa, 1.5g of Pd2(dba)31.8ml of (t-Bu)3After dissolving P in 260ml of toluene, the mixture was stirred under reflux. The reaction was confirmed by Thin Layer Chromatography (TLC), and after water was added, the reaction was terminated. The organic layer was extracted with Methylcellulose (MC), and subjected to filtration under reduced pressure followed by column purification and recrystallization to obtain 9.5g (yield 70%) of IM 1.
Synthesis of intermediates IM2 to IM7
IM2 to IM7 were synthesized in the same manner as the above-mentioned IM1, except that the starting materials were changed as shown in Table 1 below.
TABLE 1
Synthesis of Compounds
Using the above intermediates IM1 to IM7, the target compounds were synthesized as follows.
Synthesis of Compound 1
In a round-bottomed flask, 5.0g of IM1, 5.9g of 1-bromo-3-iodobenzene, 2.1g of t-BuONa, 0.6g of Pd2(dba)30.9ml of (t-Bu)3P was dissolved in 160ml of toluene, followed by stirring under reflux. The reaction was confirmed by Thin Layer Chromatography (TLC), and after water was added, the reaction was terminated. The organic layer was extracted with Methylcellulose (MC), filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 4.4g (yield 60%) of IM 1-1.
In a round-bottomed flask, 2.0g of the above IM1-1, 1.8g of N- ([1,1' -biphenylyl) benzene]-4-yl) - [1,1':4', 1' -terphenyl]-4-amine, 0.6g of t-BuONa, 0.15g of Pd2(dba)30.2ml of (t-Bu)3After dissolving P in 60ml of toluene, the mixture was stirred under reflux. The reaction was confirmed by Thin Layer Chromatography (TLC), and after water was added, the reaction was terminated. The organic layer was extracted with Methylcellulose (MC), and subjected to filtration under reduced pressure followed by column purification and recrystallization to obtain 2.4g (yield 73%) of compound 1.
m/z：806.33(100.0％)、807.33(65.7％)、808.34(21.0％)、809.34(4.6％)
Synthesis of Compound 2
Compound 2 was synthesized in the same manner as Compound 1 except that IM1 and N- ([1,1' -biphenyl ] -4-yl) - [1,1':4', 1' -terphenyl ] -4-amine were replaced with IM2 and bis ([1,1' -biphenyl ] -4-yl) amine (yield: 70%).
m/z：806.33(100.0％)、807.33(65.7％)、808.34(21.0％)、809.34(4.6％)
Synthesis of Compound 3
Compound 3 was synthesized in the same manner as Compound 1 except that IM3 and bis ([1,1' -biphenyl ] -4-yl) amine were used instead of IM1 and N- ([1,1' -biphenyl ] -4-yl) - [1,1':4', 1' -terphenyl ] -4-amine (yield 65%).
m/z：806.33(100.0％)、807.33(65.7％)、808.34(21.0％)、809.34(4.6％)
Synthesis of Compound 4
Compound 4 was synthesized in the same manner as Compound 1 except that IM4 and bis ([1,1' -biphenyl ] -4-yl) amine were used instead of IM1 and N- ([1,1' -biphenyl ] -4-yl) - [1,1':4', 1' -terphenyl ] -4-amine (yield 67%).
m/z：780.31(100.0％)、781.32(63.2％)、782.32(19.9％)、783.32(4.2％)
Synthesis of Compound 5
Compound 5 was synthesized in the same manner as Compound 1 except that IM5 and bis ([1,1' -biphenyl ] -4-yl) amine were used instead of IM1 and N- ([1,1' -biphenyl ] -4-yl) - [1,1':4', 1' -terphenyl ] -4-amine (yield 67%).
m/z：830.33(100.0％)、831.33(67.8％)、832.34(22.5％)、833.34(5.0％)
Synthesis of Compound 6
Compound 6 was synthesized in the same manner as Compound 1 using N- ([1,1' -biphenyl ] -4-yl) triphenylene-2-amine instead of N- ([1,1' -biphenyl ] -4-yl) - [1,1':4', 1' -terphenyl ] -4-amine (yield 63%).
m/z：804.31(100.0％)、805.32(65.4％)、806.32(21.2％)、807.32(4.6％)
Synthesis of Compound 7
Compound 7 was synthesized in the same manner as compound 1 using IM2, 3, 5-dichloro-1, 1' -biphenyl and bis ([1,1' -biphenyl ] -4-yl) amine instead of IM1, 1-bromo-3-iodobenzene and N- ([1,1' -biphenyl ] -4-yl) - [1,1':4',1 "-terphenyl ] -4-amine (yield 67%).
m/z：882.36(100.0％)、883.36(72.1％)、884.37(25.7％)、885.37(6.1％)、886.37(1.1％)
Synthesis of Compound 8
Compound 8 was synthesized in the same manner as Compound 1, using 3, 5-dichloro-1, 1':4',1 '-terphenyl and bis ([1,1' -biphenyl ] -4-yl) amine in place of 1-bromo-3-iodobenzene and N- ([1,1 '-biphenyl ] -4-yl) - [1,1':4', 1' -terphenyl ] -4-amine (yield 65%).
m/z：882.36(100.0％)、883.36(72.1％)、884.37(25.7％)、885.37(6.1％)、886.37(1.1％)
Synthesis of Compound 9
Compound 9 (yield 70%) was synthesized in the same manner as Compound 1 using 2- (3, 5-dichlorophenyl) triphenylene and N-phenyl- [1,1 '-biphenyl ] -4-amine instead of 1-bromo-3-iodobenzene and N- ([1,1' -biphenyl ] -4-yl) - [1,1':4',1 "-terphenyl ] -4-amine.
m/z：880.35(100.0％)、881.35(71.9％)、882.35(26.2％)、883.36(5.9％)、884.36(1.1％)
Synthesis of Compound 10
Compound 10 was synthesized in the same manner as compound 1 using IM2, 1-bromo-2-iodobenzene, and bis ([1,1 '-biphenyl ] -4-yl) amine instead of IM1, 1-bromo-3-iodobenzene, and N- ([1,1' -biphenyl ] -4-yl) - [1,1':4',1 "-terphenyl ] -4-amine (yield 43%).
m/z：806.33(100.0％)、807.33(65.7％)、808.34(21.0％)、809.34(4.6％)
Synthesis of Compound 11
Compound 11 was synthesized in the same manner as compound 1 using IM6 instead of IM1 (yield 70%).
m/z：822.31(100.0％)、823.31(66.2％)、824.31(21.7％)、824.30(4.5％)、825.32(4.4％)、825.31(3.3％)
Synthesis of Compound 12
Compound 12 was synthesized in the same manner as compound 1 using IM7, 3, 5-dichloro-1, 1' -biphenyl and bis ([1,1' -biphenyl ] -4-yl) amine instead of IM1, 1-bromo-3-iodobenzene and N- ([1,1' -biphenyl ] -4-yl) - [1,1':4',1 "-terphenyl ] -4-amine (yield 65%).
m/z：898.34(100.0％)、899.34(73.5％)、900.34(26.2％)、901.35(5.9％)、900.33(4.5％)、901.34(3.6％)、902.34(1.2％)、902.35(1.1％)
Synthesis of Compound 13
Compound 13 was synthesized in the same manner as Compound 1, using IM6, 3, 5-dichloro-1, 1':4',1 '-terphenyl and bis ([1,1' -biphenyl ] -4-yl) amine in place of IM1, 1-bromo-3-iodobenzene and N- ([1,1 '-biphenyl ] -4-yl) - [1,1':4', 1' -terphenyl ] -4-amine (yield 65%).
m/z：898.34(100.0％)、899.34(73.5％)、900.34(26.2％)、901.35(5.9％)、900.33(4.5％)、901.34(3.6％)、902.34(1.2％)、902.35(1.1％)
Synthesis of Compound 14
Compound 14 was synthesized in the same manner as Compound 1, using 1M6, 2- (3, 5-dichlorophenyl) triphenylene and N-phenyl- [1,1' -biphenyl ] -4-amine instead of IM1, 1-bromo-3-iodobenzene and N- ([1,1' -biphenyl ] -4-yl) - [1,1':4', 1' -terphenyl ] -4-amine (yield 62%).
m/z：896.32(100.0％)、897.33(71.9％)、898.33(26.0％)、899.33(6.2％)、898.32(5.1％)、899.32(3.3％)、897.32(1.5％)、900.33(1.2％)、900.34(1.0％)
Synthesis of Compound 15
Compound 15 was synthesized in the same manner as compound 1 using IM7, 1-bromo-2-iodobenzene, and bis ([1,1 '-biphenyl ] -4-yl) amine instead of IM1, 1-bromo-3-iodobenzene, and N- ([1,1' -biphenyl ] -4-yl) - [1,1':4',1 "-terphenyl ] -4-amine (yield 45%).
m/z：822.31(100.0％)、823.31(66.2％)、824.31(21.7％)、824.30(4.5％)、825.32(4.4％)、825.31(3.3％)
Preparation of organic light-emitting device
Example 1
By ultrasonic pairing of distilled water
The glass substrate coated with Indium Tin Oxide (ITO) into a thin film was washed. After the completion of the distilled water washing, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a plasma cleaner, cleaned with oxygen plasma for 5 minutes, and then deposited on the indium tin oxide substrate as a hole injection layer by a thermal vacuum deposition apparatus (thermal evaporator)
HI01, preparing a film
The HATCN of (2) is formed as a hole transport layer
HT01 (g) as a light-emitting auxiliary layer
The light-emitting layer was doped with 3% BH 01: BD01, to
Film formation is performed. Then, as an electron transport layer
ET 01: liq (1: 1) is subjected to film formation, and then
LiF, and,
Aluminum (A) of (A)l) film formation and sealing (Encapsulation) of the device in a glove box, thereby producing an organic light-emitting device.
Examples 2 to 15
Compounds 2 to 15 were used in place of compound 1 in the same manner as in example 1, respectively, to prepare organic light-emitting devices.
Comparative example 1 and comparative example 6
Organic light-emitting devices were prepared in the same manner as in example 1, using ref.1 to ref.6, respectively, instead of compound 1 for film formation.
Performance evaluation of organic light-emitting device
The performance of the organic light emitting devices of examples and comparative examples was evaluated by applying a voltage to inject electrons and holes using a gishley 2400source measurement unit (kinetpley 2400source measurement unit), measuring the luminance at the time of light emission using a Konica Minolta (Konica Minolta) spectroradiometer (CS-2000), thereby measuring the current density and luminance with respect to the applied voltage under atmospheric pressure, and the results thereof are shown in the following table 2.
TABLE 2
| Op.V | mA/cm2 | Cd/A | CIEx | CIEy | LT99 | |
| Example 1 | 4.1 | 10 | 34.5 | 0.684 | 0.316 | 158 |
| Example 2 | 4.1 | 10 | 34.0 | 0.685 | 0.315 | 160 |
| Example 3 | 4.1 | 10 | 34.0 | 0.685 | 0.314 | 154 |
| Example 4 | 4.1 | 10 | 34.8 | 0.685 | 0.315 | 152 |
| Example 5 | 4.1 | 10 | 34.5 | 0.685 | 0.315 | 152 |
| Example 6 | 4.1 | 10 | 35.3 | 0.685 | 0.315 | 155 |
| Example 7 | 4.2 | 10 | 36.5 | 0.685 | 0.315 | 152 |
| Example 8 | 4.2 | 10 | 36.2 | 0.685 | 0.315 | 152 |
| Example 9 | 4.2 | 10 | 36.1 | 0.684 | 0.315 | 157 |
| Example 10 | 3.8 | 10 | 30.5 | 0.685 | 0.315 | 127 |
| Example 11 | 4.3 | 10 | 37.5 | 0.683 | 0.316 | 135 |
| Example 12 | 4.4 | 10 | 38.5 | 0.684 | 0.316 | 135 |
| Example 13 | 4.4 | 10 | 38.4 | 0.685 | 0.315 | 135 |
| Example 14 | 4.4 | 10 | 38.5 | 0.685 | 0.315 | 140 |
| Example 15 | 3.8 | 10 | 31.3 | 0.683 | 0.316 | 129 |
| Comparative example 1 | 5.2 | 10 | 18.3 | 0.676 | 0.322 | 35 |
| Comparative example 2 | 4.9 | 10 | 20.5 | 0.680 | 0.320 | 70 |
| Comparative example 3 | 6.2 | 10 | 11.8 | 0.670 | 0.330 | 10 |
| Comparative example 4 | 4.5 | 10 | 29.2 | 0.685 | 0.317 | 65 |
| Comparative example 5 | 4.6 | 10 | 23.0 | 0.682 | 0.315 | 54 |
| Comparative example 6 | 4.7 | 10 | 26.5 | 0.683 | 0.316 | 90 |
As shown in table 2, it was confirmed that examples 1 to 15 using the compound of the present invention as a hole transport layer exhibited higher efficiency and longer life and lower driving voltage than comparative examples 1 to 6.
More specifically, in the examples of the present invention, dibenzofuran or dibenzothiophene is directly bonded to nitrogen, has fast hole mobility and a low driving voltage, compared to comparative examples 1 and 2, and two nitrogens are bonded to meta (1, 3-phenylene) or ortho (1, 2-phenylene) of phenylene, forming a deep HOMO level and having high LUMO and T1, compared to comparative example 3, thereby exhibiting excellent efficiency and lifetime increasing effects.
In addition, the example of the present invention has nonpolar aryl groups and no fluorene, and exhibits an effect of improving efficiency and lifetime due to driving stability while forming a deep HOMO level, as compared to comparative example 4.
Also, the examples of the present invention include only 1 heteroaryl group such as dibenzofuran or dibenzothiophene, minimize bulky characteristics, induce effective pi stacking between molecules, make molecular arrangement excellent, improve hole mobility, suppress roll-off phenomenon, have a low driving voltage, exhibit high efficiency and long life, compared to comparative example 5.
In the examples of the present invention, 2 nitrogens are connected to the meta (1, 3-phenylene) or ortho (1, 2-phenylene) position of the phenylene linker, as compared to comparative example 6, so that electrons can be distributed in a concentrated manner among the 2 nitrogens while maintaining high LUMO and T1, thereby exhibiting low voltage, high efficiency, and long life characteristics.
From the evaluation results as described above, it was judged that the compound of the present invention reduces the driving voltage of the organic light emitting device and is effective in improving the efficiency and lifetime.
The above description of the present invention is intended to be illustrative, and it will be understood by those skilled in the art that the present invention may be easily modified in other specific forms without changing the technical spirit or essential features of the present invention. It is therefore to be understood that the above described embodiments are illustrative in all respects, rather than restrictive. For example, each component described as a single type may be implemented as being dispersed, and similarly, a plurality of components described as being dispersed may be implemented as being combined.
The scope of the present invention is indicated by the appended claims rather than the foregoing detailed description, and all changes and modifications that come within the meaning and range of equivalency of the claims are to be construed as being included in the scope thereof.
Claims (17)
1. A compound represented by the following chemical formula 1,
chemical formula 1
In the chemical formula 1, the first and second organic solvents,
x is O or S, and X is O or S,
Ar1to Ar3Each independently is substituted or unsubstituted C6～C50But, not fluorene,
R1to R2Each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Or a substituted or unsubstituted C6～C30Can be at a plurality of adjacent R1R is2With or without the formation of a ring therebetween,
R3to R4Each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Or a substituted or unsubstituted C6～C30The aryl group of (a) is,
l and n are each independently 0 or an integer of 1 to 3, and m is 0 or an integer of 1 to 4.
2. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2,
chemical formula 2
3. The compound according to claim 2, wherein the chemical formula 2 is represented by the following chemical formula 3 or chemical formula 4,
chemical formula 3
Chemical formula 4
In the chemical formula 4, the first and second organic solvents,
Ar2and Ar3Each independently being a substituted or unsubstituted C other than fluorene6～C50Aryl of (A), however, Ar2And Ar3At least one of them is C14～C50Aryl group of (1).
4. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 5,
chemical formula 5
5. The compound according to claim 4, wherein the chemical formula 5 is represented by the following chemical formula 6,
chemical formula 6
6. A compound according to any one of claims 1 to 5, wherein R is1And R2Each independently hydrogen, deuterium or phenyl.
7. A compound of claim 1,2 or 4 wherein R is3And R4Each independently hydrogen, deuterium, or substituted or unsubstituted C1～C5Alkyl group of (1).
8. A compound of claim 1,2 or 4 wherein R is4Is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group, or a substituted or unsubstituted triphenylene group.
9. A compound according to any one of claims 1 to 5, wherein X is O.
10. A compound according to any one of claims 1 to 5, wherein X is S.
11. A compound according to any one of claims 1 to 5, wherein Ar is Ar1To Ar3Each independently selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene, and combinations thereof.
12. A compound according to any one of claims 1 to 5, wherein Ar is Ar1To Ar3At least one of which is naphthyl, phenanthrene, terphenyl or triphenylene.
13. A compound according to any one of claims 1 to 5, wherein Ar is Ar1To Ar3At least one of which is terphenyl or triphenylene.
14. The compound of claim 1, wherein Compound 1 is one of the following compounds,
15. an organic light-emitting device characterized by comprising an organic layer containing the compound according to any one of claims 1 to 14 between a first electrode and a second electrode.
16. The organic light-emitting device according to claim 15, wherein the organic layer is one or more of a hole injection layer, a hole transport layer, and a light-emission auxiliary layer.
17. The organic light-emitting device according to claim 16, wherein the organic layer is a light-emission auxiliary layer disposed between the hole-transporting layer and the light-emitting layer.
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| CN113121361A (en) * | 2021-03-31 | 2021-07-16 | 吉林奥来德光电材料股份有限公司 | Hole transport material with phenanthrene diarylamine structure and preparation method and application thereof |
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| CN107801393A (en) * | 2016-06-28 | 2018-03-13 | 德山新勒克斯有限公司 | Organic electroluminescence device compound, organic electroluminescence device and its electronic installation using the compound |
| WO2018016786A1 (en) * | 2016-07-22 | 2018-01-25 | 덕산네오룩스 주식회사 | Compound for organic electronic device, organic electronic device using same, and electronic apparatus thereof |
| CN106478566A (en) * | 2016-09-27 | 2017-03-08 | 上海道亦化工科技有限公司 | Organic electroluminescent compounds and its organic electroluminescence device based on dibenzofurans |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113816894A (en) * | 2020-06-19 | 2021-12-21 | 广州华睿光电材料有限公司 | Aromatic amine compound and application thereof in organic electronic device |
| CN113121361A (en) * | 2021-03-31 | 2021-07-16 | 吉林奥来德光电材料股份有限公司 | Hole transport material with phenanthrene diarylamine structure and preparation method and application thereof |
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| Publication number | Publication date |
|---|---|
| KR20230171910A (en) | 2023-12-21 |
| KR20200052174A (en) | 2020-05-14 |
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