CN110551087A - 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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- CN110551087A CN110551087A CN201910461939.0A CN201910461939A CN110551087A CN 110551087 A CN110551087 A CN 110551087A CN 201910461939 A CN201910461939 A CN 201910461939A CN 110551087 A CN110551087 A CN 110551087A
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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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. At this time, 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.
One 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,
R1To R11Each 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～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30heteroaryl of (a), adjacent multiple R3r is4R is7R is8R is10R is11And R1And R2May or may not combine to form a ring,
R12And R13Each 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～C30The thioether group of (a) is,
L1to L4Each independently is a direct bond, substituted or unsubstituted C6～C30Or substituted or unsubstituted C5～C30The heteroarylene group of (a) is,
l, p and q are each independently 0 or an integer of 1 to 4, m, n and o are each independently 0 or an integer of 1 to 3, and r is 0 or an integer of 1 to 2.
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.
The arylamine compound of one embodiment of the present invention has 2 fluorenyl groups, one fluorenyl group having the 2 nd position as a linking position and the other fluorenyl group having the 1 st, 3 rd or 4 th position as a linking position, and is bonded to a linking group which is linked at a meta-position or an ortho-position. By having such benzofuran or dibenzothiophene, a deep Highest Occupied Molecular Orbital (HOMO) level suitable for the light-emitting auxiliary layer can be formed. Thus, an organic light emitting device with low voltage and high efficiency can be realized.
Also, the compound according to an embodiment of the present invention can maintain high Lowest Unoccupied Molecular Orbital (LUMO) and T1, which easily block electrons, from dibenzofuran or dibenzothiophene having excellent electron tolerance by combining a linking group attached at an ortho-or meta-position with nitrogen of arylamine. Thus, the exciton confinement effect in the light-emitting layer can be maximized, and a high-efficiency organic light-emitting device can be realized.
Also, the compound of an example of the present invention increases pi-conjugation by 2 fluorenyl groups and dibenzofuran or dibenzothiophene, and improves Hole Mobility (Hole Mobility), and can realize a long-life organic light emitting device by suppressing a roll-off phenomenon.
Further, the compound according to an embodiment of the present invention can form a high Tg by introducing dibenzofuran or dibenzothiophene together with 2 fluorene groups, and can prevent recrystallization of a thin film and ensure driving stability of an organic light emitting device, thereby realizing a long-life organic light emitting device.
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: anode
2000: cathode 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. The term "step(s)" or "step(s)" used throughout the present specification does not mean "step(s) used for.
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, benzoAromatic rings of a base, an anthryl, a stilbene group, a pyrenyl group and the like, "heteroaryl" as C containing at least one hetero element3-30The aromatic ring of (a) is, for example, meant to include a ring selected from the group consisting of pyrrolinyl, pyrazinyl, pyridyl, indolyl, isoindolyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, benzothienyl, dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthryl cry yl, acridinyl, phenanthrolinyl, thienyl, and a ring selected from the group consisting of pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazolyl ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, thiadiazo ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, dibenzo ringFuran ring and dibenzothiophene ring.
Throughout the present specification, the term "substituted or unsubstituted" may mean that the substituent is 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 a hydrogen bonded to the carbon at position 9 and substituted or unsubstituted C1-20Alkyl, 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,
R1To R11Each 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～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30Heteroaryl of (a), adjacent multiple R3R is4R is7R is8R is10R is11And R1And R2May or may not combine to form a ring,
R12And R13Each 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～C30The thioether group of (a) is,
L1To L4Each independently is a direct bond, substituted or unsubstituted C6～C30Or substituted or unsubstituted C5～C30The heteroarylene group of (a) is,
l, p and q are each independently 0 or an integer of 1 to 4, m, n and o are each independently 0 or an integer of 1 to 3, and r is 0 or an integer of 1 to 2.
The arylamine compound of one embodiment of the present invention has 2 fluorenyl groups, one of which has the 2 nd position as a connecting position and the other of which has the 1 st, 3 rd or 4 th position as a connecting position, and by having dibenzofuran or dibenzothiophene combined with a connecting group connected in a meta-position or an ortho-position, a deep HOMO level suitable for a light-emission auxiliary layer can be formed. Thus, an organic light emitting device with low voltage and high efficiency can be realized.
Further, the compound of one embodiment of the present invention can maintain high LUMO and T1, which easily block electrons, from dibenzofuran or dibenzothiophene having excellent electron tolerance by combining a linking group attached at an ortho-or meta-position with the nitrogen of arylamine. Thus, the exciton confinement effect in the light-emitting layer can be maximized, and a high-efficiency organic light-emitting device can be realized.
Also, the compound of an example of the present invention increases pi-conjugation by 2 fluorenyl groups and dibenzofuran or dibenzothiophene, and improves Hole Mobility (Hole Mobility), and can realize a long-life organic light emitting device by suppressing a roll-off phenomenon.
Further, the compound according to an embodiment of the present invention can form a high Tg by introducing dibenzofuran or dibenzothiophene together with 2 fluorene groups, and can prevent recrystallization of a thin film and ensure driving stability of an organic light emitting device, thereby realizing a long-life organic light emitting device.
In one embodiment of the present invention, the above compound may be represented by the following chemical formula 2.
Chemical formula 2
In the above-described chemical formula 2,
X、R1To R13、L2To L4L, m, n, o, p, q and r are as defined above in chemical formula 1.
The compound represented by the above chemical formula 2 is L in the above chemical formula 11In the case of direct bonding. In this case, the 2 nd position of the fluorenyl group can be directly bonded with nitrogen to lower the driving voltage.
In one embodiment of the present invention, the above compound may be represented by the following chemical formula 3.
Chemical formula 3
In the above-mentioned chemical formula 3,
X、R1To R13、L2、L3L, m, n, o, p, q and r are as defined above in chemical formula 1.
The compound represented by the above chemical formula 3 is L in the above chemical formula 11And L4In the case of direct bonding. In this case, the 2 nd position in one fluorenyl group is directly bonded to nitrogen, and the 1 st, 3 rd or 4 th position in the other fluorenyl group is directly bonded to nitrogen, whereby a faster hole mobility can be achieved, whereby a roll-off phenomenon can be suppressed and a long life can be achieved.
In one embodiment of the present invention, the above compound may be represented by the following chemical formula 4 or chemical formula 5.
Chemical formula 4
Chemical formula 5
In the above chemical formulas 4 and 5,
X、R1To R13、L2L, m, n, o, p, q and r are as defined above in chemical formula 1.
the compound represented by the above chemical formula 4 or chemical formula 5 is L in the above chemical formula 11、L3And L4Is a direct bonding structure. In this case, one fluorenyl group is directly bonded to nitrogen at the 2 nd position, and the other fluorenyl group is directly bonded to nitrogen at the 1 st, 3 rd or 4 th position, and a tricyclic fused ring including X may be directly bonded to a phenylene linking group to maintain high T1, so that exciton blocking effect may be excellent.
In the chemical formulas 1 to 5, l, m, n, o, p, q, and r may all be 0 according to an embodiment of the present invention.
Alternatively, according to an embodiment of the present invention, in the chemical formulas 1 to 5, the R is1To R11Each independently hydrogen, deuterium, substituted or unsubstituted C1～C10Alkyl or phenyl groups.
According to an embodiment of the present invention, in the chemical formulas 1 to 5, the L is2may be a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenyl group.
Also, according to an embodiment of the present invention, in the chemical formulas 1 to 5, the R is1And R2Can each independently be hydrogen, deuterium, methyl or phenyl, R12And R13Each independently may be hydrogen, heavy hydrogen or methyl.
Also, according to an embodiment of the present invention, in the above chemical formulas 1 to chemicalIn the formula 5, R is as defined above1And R2May be phenyl, R12And R13May be a methyl group.
Also, according to an embodiment of the present invention, in the chemical formulas 1 to 5, the L is1To L4Each may be independently selected from the group consisting of a direct bond, phenylene, biphenyl, and combinations thereof.
according to an example of the present invention, in the above chemical formulas 1 to 5, the tricyclic fused ring including the above X may have the 2 nd or 4 th position as a connection position.
The number of the connecting position of the above-mentioned tricyclic fused ring may be as follows.
According to an example of the present invention, the compound represented by the above chemical formula 1 may be any one of the following compounds, specifically, may be any one of 337 th to 1120 th compounds, and may not be limited thereto. The following 337 th to 1120 th compounds contain diarylfluorene and are excellent in molecular arrangement, thereby being effective in improving lifespan.
A second embodiment of the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. The organic light emitting device described above may include 1 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 may not be limited thereto. When the compound of the present invention is used to form an organic layer, it may be used alone or in combination with a known compound.
In an example of the present invention, the organic light emitting device may include an organic layer containing a hole transport material and an organic layer containing a compound represented by the above chemical formula 1, but may not be limited thereto.
The organic light emitting device may include 1 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 an anode (anode) and a cathode (cathode).
For example, the organic light emitting device may be prepared according to the structure described in fig. 1. The organic light emitting device may be stacked with an anode (hole injection electrode 1000)/a hole injection layer 200/a hole transport layer 300/a light emitting layer 400/an electron transport layer 500/an electron injection layer 600/a cathode (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 an anode 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 anode 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 toThe deposition rate of,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, whereby the hole transport layer 300 can be formed. 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. The hole transport layer 300 according to an embodiment of the present invention may be 1 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 (basso coupoline) 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 of a conventional electron injection layer material by a vacuum deposition method, a spin coating method, a casting method, or the like.
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 cathode 2000 for injecting electrons is formed on the electron injection layer 600 by a method such as a vacuum deposition method or a sputtering method. As the cathode, 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 an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and an organic light-emitting device with a cathode structure, but also structures of organic light-emitting devices with various structures, and can also form 1 layer or 2 layers of intermediate layers according to requirements.
As described above, the thickness of each organic layer formed according to the present invention may be adjusted according to a desired degree, preferably, 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 light-emitting compound of the present embodiment can be applied to the content described in the first embodiment of the present invention, but may not be 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, but is not limited thereto.
Synthesis of intermediate IM
For the synthesis of the target compound, the intermediate IM can be synthesized by the following reaction without being limited thereto.
Synthesis of intermediate IM1
intermediate IM1 was synthesized as follows.
In a round-bottomed flask, 30.0g of dibenzo [ b, d ] was charged]Furan-4-ylboronic acid (dibenzo [ b, d ]]furan-4-ylboronic acid), 55.8g of 4 '-bromo-3-iodo-1, 1' -biphenyl (4 '-bromo-3-iodo-1, 1' -biphenyl) were dissolved in 1000ml of 1, 4-dioxane (1, 4-dioxane), and 210ml (2M) of K was placed2CO3And 4.9g of Pd (PPh)3)4thereafter, the mixture was stirred under reflux. After the reaction was confirmed by Thin Layer Chromatography (TLC), water was added to complete the reaction. The organic layer was extracted with Methylcellulose (MC), filtered under reduced pressure and recrystallized to obtain 40.7g (yield 72%) of intermediate IM 1.
Synthesis of intermediate IM2 to intermediate IM7
The following IM2 to IM10 were synthesized in the same manner as the above IM1, with changing the starting materials as shown in Table 1 below.
TABLE 1
Synthesis of intermediate OP1
Intermediate OP1 was synthesized as follows.
In a round-bottomed flask, 20.0g of the above-mentioned 3-bromo-9,9-dimethyl-9H-fluorene (3-bromo-9,9-dimethyl-9H-fluorene), 16.9g of 9, 9-dimethyl-9H-fluoren-2-amine, 10.5g of t-Buona, 2.7g of Pd2(dba)33.3ml of (t-Bu)3After P was dissolved in 400ml of toluene, the mixture was stirred under reflux. The reaction was confirmed by thin layer chromatography, and water was added to complete the reaction. The organic layer was extracted with methylcellulose, filtered under reduced pressure, and recrystallized to obtain 18.5g (yield: 63%) of OP 1.
Synthesis of intermediate OP2 to intermediate OP4
as shown in table 2 below, the following OP2 to OP4 were synthesized in the same manner as the above-described OP1, with changing the starting materials.
TABLE 2
Synthesis of Compounds
The target compounds 1 to 20 were synthesized using the above intermediates IM1 to IM10 and OP1 to OP 4.
Synthesis of Compound 1
In a round-bottomed flask, 3.0g of IM1, 3.3g of OP1, 1.1g of t-BuONa, 0.3g of Pd2(dba)30.3ml of (t-Bu)3P was dissolved in 100ml of toluene, followed by stirring under reflux. The reaction was confirmed by thin layer chromatography, and water was added to complete the reaction. The organic layer was extracted with methylcellulose, and after filtration under reduced pressure, column purification and recrystallization were performed to obtain 3.5g (yield 65%) of compound 1.
m/z：719.32(100.0％)、720.32(58.8％)、721.33(17.0％)、722.33(3.3％)
Synthesis of Compound 2
Compound 2 was synthesized in the same manner as compound 1 using IM2 instead of IM1 (yield 60%).
m/z：719.32(100.0％)、720.32(58.8％)、721.33(17.0％)、722.33(3.3％)
Synthesis of Compound 3
Compound 3 was synthesized in the same manner as compound 1 using IM3 and OP2 instead of IM1 and OP1 (yield 63%).
m/z：767.32(100.0％)、768.32(63.1％)、769.33(19.7％)、770.33(4.1％)
Synthesis of Compound 4
Compound 4 was synthesized in the same manner as compound 1 using IM4 and OP2 instead of IM1 and OP1 (yield 70%).
m/z：767.32(100.0％)、768.32(63.1％)、769.33(19.7％)、770.33(4.1％)
Synthesis of Compound 5
Compound 5 was synthesized in the same manner as compound 1 using IM5 and OP2 instead of IM1 and OP1 (yield 67%).
m/z：783.30(100.0％)、784.30(64.0％)、785.30(20.1％)、785.29(4.5％)、786.31(4.0％)、786.30(3.1％)
Synthesis of Compound 6
Compound 6 was synthesized in the same manner as compound 1 using IM6 and OP2 instead of IM1 and OP1 (yield 65%).
m/z：783.30(100.0％)、784.30(64.0％)、785.30(20.1％)、785.29(4.5％)、786.31(4.0％)、786.30(3.1％)
Synthesis of Compound 7
Compound 7 was synthesized in the same manner as compound 1 using OP2 instead of OP1 (yield 70%).
m/z：843.35(100.0％)、844.35(69.6％)、845.36(24.0％)、846.36(5.5％)
Synthesis of Compound 8
Compound 8 was synthesized in the same manner as compound 1 using IM2 and OP2 instead of IM1 and OP1 (yield 65%).
m/z：843.35(100.0％)、844.35(69.6％)、845.36(24.0％)、846.36(5.5％)
Synthesis of Compound 9
Compound 9 was synthesized in the same manner as compound 1, using OP3 instead of OP1 (yield 65%).
m/z：719.32(100.0％)、720.32(58.8％)、721.33(17.0％)、722.33(3.3％)
Synthesis of Compound 10
compound 10 was synthesized in the same manner as compound 1 using IM2 and OP3 instead of IM1 and OP1 (yield 65%).
m/z：719.32(100.0％)、720.32(58.8％)、721.33(17.0％)、722.33(3.3％)
Synthesis of Compound 11
Compound 11 was synthesized in the same manner as compound 1 using IM3 and OP4 instead of IM1 and OP1 (yield 70%).
m/z：767.32(100.0％)、768.32(63.1％)、769.33(19.7％)、770.33(4.1％)
Synthesis of Compound 12
Compound 12 was synthesized in the same manner as compound 1 using IM4 and OP4 instead of IM1 and OP1 (yield 68%).
m/z：767.32(100.0％)、768.32(63.1％)、769.33(19.7％)、770.33(4.1％)
synthesis of Compound 13
Compound 13 was synthesized in the same manner as compound 1 using IM5 and OP4 instead of IM1 and OP1 (yield 63%).
m/z：783.30(100.0％)、784.30(64.0％)、785.30(20.1％)、785.29(4.5％)、786.31(4.0％)、786.30(3.1％)
Synthesis of Compound 14
Compound 14 was synthesized in the same manner as compound 1 using IM6 and OP4 instead of IM1 and OP1 (yield 60%).
m/z：783.30(100.0％)、784.30(64.0％)、785.30(20.1％)、785.29(4.5％)、786.31(4.0％)、786.30(3.1％)
Synthesis of Compound 15
Compound 15 was synthesized in the same manner as compound 1, using OP4 instead of OP1 (yield 71%).
m/z：843.35(100.0％)、844.35(69.6％)、845.36(24.0％)、846.36(5.5％)
Synthesis of Compound 16
compound 16 was synthesized in the same manner as compound 1, using IM2 and OP4 instead of IM1 and OP1 (yield 67%).
m/z：843.35(100.0％)、844.35(69.6％)、845.36(24.0％)、846.36(5.5％)
Synthesis of Compound 17
compound 17 was synthesized in the same manner as compound 1 using IM7 and OP4 instead of IM1 and OP1 (yield 65%).
m/z：843.35(100.0％)、844.35(69.6％)、845.36(24.0％)、846.36(5.5％)
Synthesis of Compound 18
Compound 18 was synthesized in the same manner as compound 1 using IM8 and OP4 instead of IM1 and OP1 (yield 65%).
m/z：843.35(100.0％)、844.35(69.6％)、845.36(24.0％)、846.36(5.5％)
Synthesis of Compound 19
compound 19 was synthesized in the same manner as compound 1 using IM9 and OP4 instead of IM1 and OP1 (yield 60%).
m/z：859.33(100.0％)、860.33(70.5％)、861.33(24.4％)、862.34(5.4％)、861.32(4.5％)、862.33(3.4％)、863.33(1.1％)
synthesis of Compound 20
Compound 20 was synthesized in the same manner as compound 1 using IM10 and OP4 instead of IM1 and OP1 (yield 62%).
m/z：859.33(100.0％)、860.33(70.5％)、861.33(24.4％)、862.34(5.4％)、861.32(4.5％)、862.33(3.4％)、863.33(1.1％)
Preparation of organic light-emitting device
Example 1
By ultrasonic pairing of distilled waterThe 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 (cvd) apparatusHI01, preparing a filmThe HATCN of (2) is formed as a hole transport layerHT01 (g) as a light-emitting auxiliary layerThe light-emitting layer was doped with 3% BH 01: BD01, toFilm formation is performed. Then, as an electron transport layerET 01: liq (1: 1) is subjected to film formation, and thenL ofiF、The device was sealed in a glove box (Encapsulation) to prepare an organic light emitting device.
Examples 2 to 20
In the same manner as in example 1, compound 2 to compound 20 were used instead of compound 1, thereby preparing an organic light-emitting device.
Comparative examples 1 to 9
In the same manner as in example 1, ref.1 to ref.9 were used instead of compound 1, thereby preparing an organic light-emitting device.
Performance evaluation of organic light-emitting device
The organic light emitting devices of examples and comparative examples were evaluated for performance by applying a voltage to inject electrons and holes using a gishley 2400source measurement unit (kinetey 2400source measurement unit), measuring brightness at the time of light emission using a Konica Minolta (Konica Minolta) spectroradiometer (CS-2000), and thus measuring current density and brightness with respect to the applied voltage under atmospheric pressure conditions, and the results thereof are shown in the following table 3.
TABLE 3
| Op.V | mA/cm2 | Cd/A | CIEx | CIEy | LT95 | |
| Example 1 | 4.0 | 10 | 64.4 | 0.334 | 0.612 | 208 |
| Example 2 | 4.0 | 10 | 64.0 | 0.335 | 0.611 | 202 |
| Example 3 | 4.0 | 10 | 68.8 | 0.334 | 0.610 | 235 |
| Example 4 | 4.0 | 10 | 68.1 | 0.335 | 0.610 | 235 |
| Example 5 | 4.0 | 10 | 68.0 | 0.335 | 0.610 | 232 |
| Example 6 | 4.0 | 10 | 68.2 | 0.333 | 0.611 | 230 |
| Example 7 | 4.0 | 10 | 68.0 | 0.335 | 0.610 | 242 |
| Example 8 | 4.0 | 10 | 68.5 | 0.335 | 0.611 | 240 |
| Example 9 | 4.0 | 10 | 68.2 | 0.335 | 0.612 | 220 |
| Example 10 | 4.1 | 10 | 70.1 | 0.336 | 0.610 | 215 |
| Example 11 | 4.1 | 10 | 72.0 | 0.335 | 0.610 | 258 |
| example 12 | 4.1 | 10 | 71.9 | 0.335 | 0.612 | 255 |
| Example 13 | 4.1 | 10 | 73.4 | 0.335 | 0.610 | 250 |
| Example 14 | 4.1 | 10 | 73.0 | 0.333 | 0.610 | 250 |
| Example 15 | 4.1 | 10 | 76.0 | 0.335 | 0.611 | 282 |
| Example 16 | 4.1 | 10 | 75.5 | 0.334 | 0.611 | 278 |
| Example 17 | 4.1 | 10 | 74.5 | 0.334 | 0.612 | 280 |
| example 18 | 4.1 | 10 | 74.9 | 0.334 | 0.610 | 277 |
| Example 19 | 4.1 | 10 | 76.4 | 0.334 | 0.610 | 270 |
| Example 20 | 4.1 | 10 | 76.0 | 0.334 | 0.611 | 270 |
| comparative example 1 | 4.3 | 10 | 54.0 | 0.335 | 0.612 | 74 |
| Comparative example 2 | 4.7 | 10 | 61.7 | 0.336 | 0.610 | 105 |
| Comparative example 3 | 4.3 | 10 | 60.5 | 0.335 | 0.611 | 120 |
| Comparative example 4 | 4.3 | 10 | 58.1 | 0.337 | 0.610 | 133 |
| Comparative example 5 | 4.7 | 10 | 61.4 | 0.334 | 0.612 | 115 |
| comparative example 6 | 4.4 | 10 | 60.8 | 0.335 | 0.610 | 110 |
| Comparative example 7 | 4.2 | 10 | 61.5 | 0.335 | 0.610 | 170 |
| Comparative example 8 | 4.3 | 10 | 61.8 | 0.335 | 0.610 | 162 |
| Comparative example 9 | 4.4 | 10 | 61.0 | 0.335 | 0.610 | 152 |
As shown in table 3, it was confirmed that examples 1 to 20 using the compound of the present invention as a hole transport layer had higher efficiency and longer life than comparative examples 1 to 9.
More specifically, examples 1 to 20 can introduce two fluorenes to have HOMO suitable for Hole transport and fast Hole Mobility (Hole Mobility) compared to comparative examples 1 and 2.
In addition, in many examples, the deep HOMO suitable for the light-emitting auxiliary layer can be formed using the 2 nd and 1, 3 rd or 4 th positions of the diarylfluorene as the connecting positions, as compared with comparative examples 3, 4 and 5, thereby realizing an organic light-emitting device having excellent efficiency.
In addition, in many examples, compared to comparative examples 6, 7, and 8, the organic el element can have a high LUMO and T1 with a connecting group connected at an intermediate position or an ortho position, thereby easily blocking electrons and maximizing the exciton confinement effect in the light emitting layer.
Also, in many examples, compared to comparative example 9, bulk characteristics can be minimized with the 1 st, 3 rd or 4 th position of the dialkylfluorene as a position to maintain fast hole mobility, and at the same time, pi stacking between molecules becomes easy, thin film arrangement of molecules is excellent, and roll-off phenomenon is suppressed, thereby realizing an organic light emitting device having a greatly improved 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 can be easily modified in other specific ways without changing the technical idea 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 a dispersion, and similarly, a plurality of components described as a dispersion may be implemented as a combination.
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 (12)
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,
R1to R11Each 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～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30Heteroaryl of (a), adjacent multiple R3R is4R is7R is8R is10R is11And R1And R2Can combine to form a ring or not form a ring,
R12And R13Each 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～C30The thioether group of (a) is,
L1To L4Each independently is a direct bond, substituted or unsubstituted C6～C30Or substituted or unsubstituted C5～C30the heteroarylene group of (a) is,
l, p and q are each independently 0 or an integer of 1 to 4, m, n and o are each independently 0 or an integer of 1 to 3, and r is 0 or an integer of 1 to 2.
2. The compound according to claim 1, wherein the compound is represented by the following chemical formula 2,
Chemical formula 2
In the chemical formula 2,
X、R1To R13、L2To L4L, m, n, o, p, q and r are as defined in said chemical formula 1.
3. The compound according to claim 1, wherein the compound is represented by the following chemical formula 3,
Chemical formula 3
In the chemical formula 3, the first and second organic solvents,
X、R1To R13、L2、L3L, m, n, o, p, q and r are as defined in said chemical formula 1.
4. The compound according to claim 1, wherein the compound is represented by the following chemical formula 4 or chemical formula 5,
Chemical formula 4
Chemical formula 5
In the chemical formulas 4 and 5,
X、R1To R13、L2L, m, n, o, p, q and r are as defined in said chemical formula 1.
5. A compound according to any one of claims 1 to 4, wherein L is2Is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenyl group.
6. A compound according to any one of claims 1 to 4, wherein R is1And R2each independently of the other being hydrogen, deuterium, methyl or phenyl, R12And R13Each independently hydrogen, heavy hydrogen or methyl.
7. A compound according to any one of claims 1 to 4, wherein R is1And R2Is phenyl, R12And R13Is methyl.
8. A compound according to any one of claims 1 to 4, wherein L is1To L4Each independently selected from the group consisting of direct bond, phenylenePhenyl, biphenyl, and combinations thereof.
9. A compound according to any one of claims 1 to 4, wherein the tricyclic fused ring containing X has the 2 or 4 position as the attachment position.
10. The compound of claim 1, wherein the compound is one of the following compounds,
11. An organic light-emitting device characterized by comprising an organic layer containing the compound according to any one of claims 1 to 10 between a first electrode and a second electrode.
12. The organic light-emitting device according to claim 11, wherein the organic layer is one or more of a hole injection layer, a hole transport layer, and a light-emission auxiliary layer.
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