CN106883205B - Novel compound and organic light-emitting device comprising same - Google Patents

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

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CN106883205B
CN106883205B CN201610812843.0A CN201610812843A CN106883205B CN 106883205 B CN106883205 B CN 106883205B CN 201610812843 A CN201610812843 A CN 201610812843A CN 106883205 B CN106883205 B CN 106883205B
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organic light
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咸昊完
安贤哲
金成勋
裴惟珍
金东骏
闵丙哲
韩政佑
李萤振
林东焕
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Dongjin Semichem Co Ltd
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Abstract

The present invention relates to a novel compound, and more particularly, to a novel compound which has excellent hole injection and hole transport characteristics when applied to an organic light emitting device, enables low voltage driving, has excellent electromagnetic shielding characteristics, improves hole mobility (hole mobility), realizes low voltage, high efficiency, and long life, prevents recrystallization of a thin film due to high Tg, and enables excellent driving stability.

Description

Novel compound and organic light-emitting device comprising same
Technical Field
The present invention relates to a novel compound and an organic light emitting device including the same, and more particularly, to a novel compound which has excellent hole injection and hole transport properties to enable low voltage driving, has excellent electromagnetic shielding properties, improves hole mobility (hole mobility), realizes low voltage, high efficiency and long life, prevents recrystallization of a thin film due to high Tg, and enables excellent driving stability when applied to an organic light emitting device.
Background
Recently, a self-luminous organic light emitting element which can be driven at a low voltage is more excellent in viewing angle, contrast, and the like than a Liquid Crystal Display (LCD) which is a mainstream of a flat panel display element, does not require a backlight, can be light and thin, is advantageous in power consumption, and has a wide color reproduction range, and thus has attracted attention as a next generation display element.
Materials used as an organic layer in an organic light emitting element are broadly classified by function into a light emitting material, a hole injecting material, a hole transporting material, an electron injecting material, and the like. The light-emitting materials may be classified into high-molecular and low-molecular materials according to molecular weight, fluorescent materials derived from a singlet excited state of electrons and phosphorescent materials derived from a triplet excited state of electrons according to a light-emitting mechanism, and the light-emitting materials may be classified into blue, green and red light-emitting materials according to light emission colors and yellow and orange light-emitting materials required for exhibiting better natural colors. In addition, in order to increase the light emitting efficiency by an increase in color purity and energy transfer, a host/dopant system may be used as a light emitting substance. The principle is as follows: when a small amount of a dopant having a smaller energy band gap and superior light emission efficiency than that of a host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transferred to the dopant to emit light with high efficiency. In this case, since the wavelength of the host shifts 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 for such organic light emitting elements, but in the case of organic light emitting elements using conventionally known materials, there are many difficulties in practical use due to high driving voltage, low efficiency, and short lifetime. Therefore, efforts have been made to develop an organic light-emitting element having low-voltage driving, high luminance, and long lifetime by using a substance having excellent characteristics.
Disclosure of Invention
In order to solve the above problems, an object of the present invention is to provide a novel compound which has excellent hole injection and hole transport characteristics to enable low voltage driving, has excellent electromagnetic shielding characteristics, improves hole mobility (hole mobility), realizes low voltage, high efficiency and long life, prevents recrystallization of a thin film due to high Tg, and enables excellent driving stability when applied to an organic light emitting device.
Another object of the present invention is to provide an organic light emitting device including the novel compound, having excellent hole injection and hole transport characteristics, thereby enabling low voltage driving, having excellent electromagnetic shielding characteristics, improving hole mobility (hole mobility), achieving low voltage, high efficiency, a long lifetime, preventing recrystallization of a thin film due to high Tg, and enabling driving stability.
In order to achieve the above object, the present invention provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
Figure GDA0003636234680000021
In the above-mentioned formula, the compound of formula,
x is O or S, and the compound is shown in the specification,
l isA single bond; by deuterium, halogen, amino, cyano, nitro, C 1-30 Alkyl radical, C 1-30 Alkoxy radical, C 2-30 Alkenyl, silyl substituted or unsubstituted C 6-50 An arylene group; or by deuterium, halogen, amino, cyano, nitro, C 1-30 Alkyl radical, C 1-30 Alkoxy radical, C 2-30 Alkenyl, silyl substituted or unsubstituted C 2-50 A heteroarylene group, a heteroaryl group,
Ar 1 and Ar 2 Each independently is deuterium, halogen, amino, cyano, nitro, C 1-30 Alkyl radical, C 1-30 Alkoxy radical, C 2-30 Alkenyl, silyl substituted or unsubstituted C 6-50 An aryl group; or by deuterium, halogen, amino, cyano, nitro, C 1-30 Alkyl radical, C 1-30 Alkoxy radical, C 2-30 Alkenyl, silyl substituted or unsubstituted C 2-50 (ii) a heteroaryl group, wherein,
R 1 、R 2 、R 3 、R 4 and R 5 Each independently is hydrogen; deuterium; halogen; an amino group; a cyano group; a nitro group; a silane group; c substituted or unsubstituted by deuterium, halogen, amino, cyano, nitro 1-30 An alkyl group; c substituted or unsubstituted by deuterium, halogen, amino, cyano, nitro 2-30 An alkenyl group; c substituted or unsubstituted by deuterium, halogen, amino, cyano, nitro 2-30 An alkynyl group; c substituted or unsubstituted by deuterium, halogen, amino, cyano, nitro 1-30 An alkoxy group; c substituted or unsubstituted by deuterium, halogen, amino, cyano, nitro 6-30 An aryloxy group; by deuterium, halogen, amino, cyano, nitro, C 1-30 Alkyl radical, C 1-30 Alkoxy radical, C 2-30 Alkenyl, silyl substituted or unsubstituted C 6-50 An aryl group; or by deuterium, halogen, amino, cyano, nitro, C 1-30 Alkyl radical, C 1-30 Alkoxy radical, C 2-30 Alkenyl, silyl substituted or unsubstituted C 2-50 A heteroaryl group.
In addition, the present invention provides an organic light emitting element comprising the compound represented by the above chemical formula 1.
When the novel compound according to the present invention is applied to an organic light emitting device, the novel compound is excellent in hole injection and hole transport properties, thereby enabling low voltage driving, is excellent in electromagnetic shielding properties, improves hole mobility (hole mobility), realizes low voltage, high efficiency and long life, prevents recrystallization of a thin film due to high Tg, and enables excellent driving stability.
Drawings
FIG. 1 is a diagram schematically showing a cross-section of an OLED according to an embodiment of the present invention.
Description of the symbols
10: substrate
11: anode
12: hole injection layer
13: hole transport layer
14: luminescent layer
15: electron transport layer
16: cathode electrode
Detailed Description
The compound of the present invention is represented by the following chemical formula 1.
[ chemical formula 1]
Figure GDA0003636234680000041
In the above-mentioned formula, the compound of formula,
x is O or S, and X is O or S,
l is a single bond; by deuterium, halogen, amino, cyano, nitro, C 1-30 Alkyl radical, C 1-30 Alkoxy radical, C 2-30 Alkenyl, silyl substituted or unsubstituted C 6-50 An arylene group; or by deuterium, halogen, amino, cyano, nitro, C 1-30 Alkyl radical, C 1-30 Alkoxy radical, C 2-30 Alkenyl, silyl substituted or unsubstituted C 2-50 A heteroarylene group, a heteroaryl group,
Ar 1 and Ar 2 Each independently of the others being deuterium, halogen, amino, cyano, nitro, C 1-30 Alkyl radical, C 1-30 Alkoxy radical, C 2-30 Alkenyl, silyl substituted or unsubstituted C 6-50 An aryl group; or by deuterium, halogen, amino groupsCyano, nitro, C 1-30 Alkyl radical, C 1-30 Alkoxy radical, C 2-30 Alkenyl, silyl substituted or unsubstituted C 2-50 (ii) a heteroaryl group, wherein,
R 1 、R 2 、R 3 、R 4 and R 5 Each independently is hydrogen; deuterium; a halogen; an amino group; a cyano group; a nitro group; a silane group; c substituted or unsubstituted by deuterium, halogen, amino, cyano, nitro 1-30 An alkyl group; c substituted or unsubstituted by deuterium, halogen, amino, cyano, nitro 2-30 An alkenyl group; c substituted or unsubstituted by deuterium, halogen, amino, cyano, nitro 2-30 An alkynyl group; c substituted or unsubstituted by deuterium, halogen, amino, cyano, nitro 1-30 An alkoxy group; c substituted or unsubstituted by deuterium, halogen, amino, cyano, nitro 6-30 An aryloxy group; by deuterium, halogen, amino, cyano, nitro, C 1-30 Alkyl radical, C 1-30 Alkoxy radical, C 2-30 Alkenyl, silyl substituted or unsubstituted C 6-50 An aryl group; or by deuterium, halogen, amino, cyano, nitro, C 1-30 Alkyl radical, C 1-30 Alkoxy radical, C 2-30 Alkenyl, silyl substituted or unsubstituted C 2-50 A heteroaryl group.
Specifically, L, Ar 1 And Ar 2 Aromatic amines may not be included; more specifically, Ar 1 And Ar 2 At least one of which may comprise fluorene. In this case, a low-voltage drive and a high-efficiency organic light-emitting element having more excellent hole mobility can be realized.
In the present invention, specific examples of the compound represented by the above chemical formula 1 are as follows:
Figure GDA0003636234680000051
Figure GDA0003636234680000061
Figure GDA0003636234680000071
Figure GDA0003636234680000081
Figure GDA0003636234680000091
Figure GDA0003636234680000101
Figure GDA0003636234680000111
Figure GDA0003636234680000121
Figure GDA0003636234680000131
Figure GDA0003636234680000141
Figure GDA0003636234680000151
Figure GDA0003636234680000161
Figure GDA0003636234680000171
Figure GDA0003636234680000181
Figure GDA0003636234680000191
Figure GDA0003636234680000201
Figure GDA0003636234680000211
Figure GDA0003636234680000221
Figure GDA0003636234680000231
Figure GDA0003636234680000241
Figure GDA0003636234680000251
Figure GDA0003636234680000261
Figure GDA0003636234680000271
Figure GDA0003636234680000281
Figure GDA0003636234680000291
Figure GDA0003636234680000301
Figure GDA0003636234680000311
Figure GDA0003636234680000321
Figure GDA0003636234680000331
Figure GDA0003636234680000341
Figure GDA0003636234680000351
Figure GDA0003636234680000361
Figure GDA0003636234680000371
Figure GDA0003636234680000381
Figure GDA0003636234680000391
Figure GDA0003636234680000401
Figure GDA0003636234680000411
Figure GDA0003636234680000421
Figure GDA0003636234680000431
Figure GDA0003636234680000441
Figure GDA0003636234680000451
Figure GDA0003636234680000461
Figure GDA0003636234680000471
Figure GDA0003636234680000481
Figure GDA0003636234680000491
the compound represented by chemical formula 1 according to the present invention has the following advantages when applied to an organic light emitting element:
1. the benzofuran/benzothiophene combines with an arylamine to form a HOMO suitable for hole injection and hole transport. Low voltage driving is possible.
2. The benzofuran/benzothiophene is combined with an arylamine to form a LUMO that is easily electromagnetically shielded. High efficiency can be achieved.
3. The hole mobility is increased by the substitution of the 3-position of benzofuran/thiophene. Low voltage, high efficiency and long service life can be realized.
4. Preventing recrystallization of the film due to high Tg. The driving stability is improved.
Further, the compound of the present invention can be produced by the following reaction formula 1.
[ reaction formula 1]
Figure GDA0003636234680000492
L, Ar in the above reaction scheme 1 1 、Ar 2 、R 1 、R 2 、R 3 、R 4 、R 5 Is as defined in chemical formula 1.
In addition, the present invention provides an organic light emitting element including the compound represented by the above chemical formula 1 in an organic layer. Specifically, a hole injecting substance or a hole transporting substance, more specifically, a hole transporting substance is contained, and in this case, the compound of the present invention may be used alone or together with a known organic light emitting compound. In particular, L, Ar in chemical formula 1 1 And Ar 2 Not containing aromatic amines, Ar 1 Or Ar 2 When fluorene is included, an organic light-emitting element which is driven at a low voltage and has high efficiency due to more excellent hole mobility (electroluminescence) can be realized.
Further, the organic light emitting device of the present invention includes 1 or more organic layers containing the compound represented by the above chemical formula 1, and the method for manufacturing the organic light emitting device is explained as follows:
the organic light emitting device may include at least 1 organic layer 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).
First, an anode electrode substance having a high work function is deposited on the substrate to form an anode. In this case, the substrate used in a general organic light-emitting element can be used, and a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, workability, and water repellency is particularly preferably used. As the material for the anode electrode, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), or tin oxide (SnO) which is transparent and excellent in conductivity can be used 2 ) Zinc oxide (ZnO), and the like. The material for the anode electrode may be deposited by a common anode formation method, specifically, by a deposition method or a sputtering method.
Next, a substance for forming a hole injection layer may be formed on the anode electrode by a method such as vacuum deposition, spin coating, casting, or LB (Langmuir-Blodgett). When the hole injection layer is formed by the vacuum deposition method, the deposition conditions may vary depending on the compound used as the material of the hole injection layer, the structure and thermodynamic characteristics of the target hole injection layer, and the like, but in general, the deposition temperature may be 50 to 500 ℃ or 10 -8 To 10 -3 Vacuum degree of torr, 0.01 to
Figure GDA0003636234680000501
The vapor deposition rate is set to be in the range of sec,
Figure GDA0003636234680000502
the layer thickness is suitably selected within the range of 5 μm.
The compound represented by chemical formula 1 of the present invention may be used as the hole injection layer material, or may be used together with a known material. The known substance is not particularly limited, and a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429 or a starburst amine derivative, i.e., TCTA (4,4' -tris (N-carbazolyl) triphenylamine, can be used) m-MTDATA (4,4 '-tris (3-methylphenylamino) triphenylamine), m-MTDAPB (4,4' -tris (3-methylphenylamino) phenoxybenzene), HI-406 (N) 1 ,N 1 '- (biphenyl-4, 4' -diyl) bis (N) 1 - (Naphthalen-1-yl) -N 4 ,N 4 Diphenylbenzene-1, 4-diamine), etc. as a hole injection layer material.
Then, a substance for forming a hole transport layer may be formed on the hole injection layer by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like. When the hole transport layer is formed by the vacuum deposition method, the deposition conditions may vary depending on the compound used, but in general, the conditions are preferably selected within a range substantially equivalent to the conditions for forming the hole injection layer.
The compound represented by chemical formula 1 of the present invention can be used as the hole transport layer material, or can be used together with a known material. The known substance is not particularly limited, and can be arbitrarily selected from among conventional known substances used for a hole transport layer. Specifically, as the hole transport layer material, a carbazole derivative such as N-phenylcarbazole or polyvinylcarbazole, or a general amine derivative having an aromatic condensed ring such as N, N ' -bis (3-methylphenyl) -N, N ' -diphenyl- [1, 1-biphenyl ] -4,4' -diamine (TPD) or N, N ' -bis (naphthalene-1-yl) -N, N ' -diphenylbenzidine (α -NPD) can be used.
Then, a light-emitting layer material may be formed on the hole-transporting layer by a method such as vacuum deposition, spin coating, casting, or LB. When the light-emitting layer is formed by the vacuum deposition method, the deposition conditions may vary depending on the compound used, but in general, the conditions are preferably selected within a range substantially equivalent to those of the hole-injecting layer. The light-emitting layer material may use a known compound as a host or a dopant.
In addition, as an example, IDE102 or IDE105, or BD142 (N) available from the yohimoto corporation (Idemitsu corporation) may be used as the fluorescent dopant for the material of the light emitting layer described above 6 ,N 12 -bis (3, 4-dimethylphenyl) -N 6 ,N 12 -two
Figure GDA0003636234680000511
Base of
Figure GDA0003636234680000512
6, 12-diamines) as phosphorescent dopants, which can be co-vacuum evaporated (doped) with the green phosphorescent dopant Ir (ppy) 3 (tris (2-phenylpyridinato) iridium), F2Irpic (bis [4, 6-difluorophenylpyridin-N, C2 'as blue phosphorescent dopant']Iridium (III) picolinate, iridium (III) bis [4, 6-di-fluorophenyl-pyrindinato-N, C2']picolinate), UDC corporation red phosphorescent dopant No. 7 RD61, and the like.
In the case where a phosphorescent dopant is used in combination in the light-emitting layer, a hole-blocking material (HBL) may be further laminated by a vacuum evaporation method or a spin coating method in order to prevent diffusion of triplet excitons or holes into the electron-transporting layer. The hole-blocking substance that can be used in this case is not particularly limited, and any one selected from known materials used as a hole-blocking material can be used. For example, there may be mentioned
Figure GDA0003636234680000521
Examples of the oxadiazole derivative, the triazole derivative, the phenanthroline derivative, and the hole-blocking material described in jp 11-329734 a1 a include Balq (bis (8-hydroxy-2-methylquinoline) -diphenoylaluminum), and phenanthroline (phenanthroline) compounds (e.g., BCP (Bathocuproine, UDC)).
In the case where an electron transport layer is formed on the light-emitting layer formed as described above, the electron transport layer may be formed by a method such as vacuum deposition, spin coating, or casting.
The electron transport layer material plays a role of stably transporting electrons injected from the electron injection electrode, and the kind thereof is not particularly limited, and for example, a quinoline derivative, particularly tris (8-hydroxyquinoline) aluminum (Alq), can be used 3 ) Or ET4(6,6' - (3, 4-bis)
Figure GDA0003636234680000522
Radical-1, 1-dimethyl-1H-silole-2, 5-diyl) di-2, 2' -bipyridine). Further, an Electron Injection Layer (EIL) which is a substance having a function of easily injecting electrons from the cathode may be stacked on the electron transport layer, and LiF, NaCl, CsF, or Li may be used as the electron injection layer substance 2 O, BaO, etc.
The conditions for vapor deposition of the electron transport layer may vary depending on the compound used, but in general, it is preferable to select the conditions within a range substantially equivalent to the conditions for formation of the hole injection layer.
Thereafter, an electron injection layer material may be formed on the electron transport layer, and in this case, a general electron injection layer material may be formed on the electron transport layer by a method such as vacuum deposition, spin coating, or casting.
Finally, a metal for forming a cathode is formed on the electron injection layer by a method such as vacuum deposition or sputtering, and the metal is used as a cathode. Here, as the metal for forming the cathode, a metal having a low work function, an alloy, a conductive compound, and a mixture thereof can be used. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. In order to obtain a top-emission device, a transmissive cathode using ITO or IZO may be used.
The organic light-emitting device of the present invention can realize not only an organic light-emitting device having an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode structure, but also structures of organic light-emitting devices having various structures, and if necessary, one or two intermediate layers may be further formed.
As described above, the thickness of each organic layer formed according to the present invention may be adjusted according to a required degree, and specifically, may be 10 to 1000nm, and more specifically, is preferably 20 to 150 nm.
In addition, the organic layer including the compound represented by chemical formula 1 according to the present invention has advantages of uniform surface and excellent morphological stability since the thickness of the organic layer can be adjusted in a molecular unit.
The organic light emitting device of the present invention, which includes the compound represented by the above chemical formula 1, has excellent hole injection and hole transport properties, thereby enabling low voltage driving, has excellent electromagnetic shielding properties, improves hole mobility (hole mobility), realizes low voltage, high efficiency, and long lifetime, can prevent recrystallization of a thin film due to high Tg, and can enable excellent driving stability.
Hereinafter, specific examples are given to help understanding of the present invention, but the following examples are only for illustrating the present invention, and the scope of the present invention is not limited to the following examples.
Synthesis of OP
Figure GDA0003636234680000531
To synthesize the target compound, OP was prepared by the above procedure.
The following synthesis method of OP1 is as follows.
Figure GDA0003636234680000532
In a round-bottom flask, 10g of N- ([1,1' -biphenyl ] was charged]-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (N- ([1,1' -biphenyl)]-4-yl) -9, 9-dimethyl-9H-fluoron-2-amine), 11.0g of 1-bromo-4-iodobenzene (1-bromo-4-iodobenze), 4.0g of t-BuONa, 1.0g of Pd 2 (dba) 3 1.6ml of (t-Bu) 3 P was dissolved in 200ml of toluene and stirred at 50 ℃. The reaction was confirmed by TLC, and after addition of water, the reaction was terminated. The organic layer was extracted with EA, which was filtered under reduced pressure and purified by column chromatography to obtain 6.72g of OP1 (yield: 47%).
The following OP2 to OP11 were synthesized in the same manner as the above OP 1.
Figure GDA0003636234680000541
Synthesis of Compound 1
Figure GDA0003636234680000542
In a round-bottomed flask, 1.13g of benzofuran-3-boronic acid (benzofuran-3-ylboronic acid), 3.0g of OP1 were dissolved in 40ml of 1, 4-bis
Figure GDA0003636234680000543
Alkane (1,4-dioxan), to which 8.5ml of K was added 2 CO 3 (2M) and 0.20g of Pd (PPh) 3 ) 4 Then, the mixture was stirred under reflux. The reaction was confirmed by TLC, and after addition of water, the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and purified on a column to obtain 12.03g of a compound (yield 63%).
m/z：553.24(100.0％)，554.24(44.8％)，555.25(9.8％)，556.25(1.5％)
Synthesis of Compound 2
Figure GDA0003636234680000551
Compound 2 was synthesized in the same manner as compound 1, using OP2 instead of OP 1. (yield 58%)
m/z：677.27(100.0％)，678.28(55.6％)，679.28(15.4％)，680.28(2.9％)
Synthesis of Compound 3
Figure GDA0003636234680000552
Compound 3 was synthesized in the same manner as compound 1, using OP3 instead of OP 1. (yield 55%)
m/z：629.27(100.0％)，630.28(51.3％)，631.28(13.1％)，632.28(2.3％)
Synthesis of Compound 4
Figure GDA0003636234680000553
Compound 4 was synthesized in the same manner as compound 1, using OP4 instead of OP 1. (yield 57%)
m/z：669.30(100.0％)，670.31(54.6％)，671.31(14.8％)，672.31(2.7％)
Synthesis of Compound 5
Figure GDA0003636234680000561
Compound 5 was synthesized in the same manner as compound 1 using OP5 instead of OP 1. (yield 50%)
m/z：629.27(100.0％)，630.28(51.3％)，631.28(13.1％)，632.28(2.3％)
Synthesis of Compound 6
Figure GDA0003636234680000562
Compound 6 was synthesized in the same manner as compound 1 using OP6 instead of OP 1. (yield 52%)
m/z：669.30(100.0％)，670.31(54.6％)，671.31(14.8％)，672.31(2.7％)
Synthesis of Compound 7
Figure GDA0003636234680000563
Compound 7 was synthesized in the same manner as compound 1 using OP7 instead of OP 1. (yield 55%)
m/z：629.27(100.0％)，630.28(51.3％)，631.28(13.1％)，632.28(2.3％)
Synthesis of Compound 8
Figure GDA0003636234680000571
Compound 8 was synthesized in the same manner as compound 1 using OP8 instead of OP 1. (yield 60%)
m/z：669.30(100.0％)，670.31(54.6％)，671.31(14.8％)，672.31(2.7％)
Synthesis of Compound 9
Figure GDA0003636234680000572
Compound 9 was synthesized in the same manner as compound 1 using OP9 instead of OP 1. (yield 48%)
m/z：629.27(100.0％)，630.28(51.3％)，631.28(13.1％)，632.28(2.3％)
Synthesis of Compound 10
Figure GDA0003636234680000573
Compound 10 was synthesized in the same manner as compound 1, using OP10 instead of OP 1. (yield 44%)
m/z：669.30(100.0％)，670.31(54.6％)，671.31(14.8％)，672.31(2.7％)
Synthesis of Compound 11
Figure GDA0003636234680000581
In a round-bottomed flask, 1.45g of benzothiophene-3-boronic acid (benzothiophene-3-ylboronic acid), 3.5g of OP1 were dissolved in 50ml of 1, 4-bis
Figure GDA0003636234680000582
Alkane (1,4-dioxan), 10.2ml of K was added 2 CO 3 (2M) and 0.23g of Pd (PPh) 3 ) 4 Then, the mixture was stirred under reflux. The reaction was confirmed by TLC, and after addition of water, the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and purified on a column to obtain 2.32g of Compound 11 (yield 60%).
m/z：569.22(100.0％)，570.22(45.5％)，571.22(10.1％)，571.21(4.5％)，572.22(2.1％)，572.23(1.4％)
Synthesis of Compound 12
Figure GDA0003636234680000583
Compound 12 was synthesized in the same manner as compound 11 using OP2 instead of OP 1. (yield 58%)
m/z：693.25(100.0％)，694.25(56.3％)，695.26(15.1％)，695.24(4.5％)，696.26(2.8％)，696.25(2.6％)
Synthesis of Compound 13
Figure GDA0003636234680000584
Compound 13 was synthesized in the same manner as compound 11 using OP3 instead of OP 1. (yield 63%)
m/z：645.25(100.0％)，646.25(52.0％)，647.26(12.9％)，647.24(4.5％)，648.25(2.4％)，648.26(2.2％)
Synthesis of Compound 14
Figure GDA0003636234680000591
Compound 14 was synthesized in the same manner as compound 11, using OP4 instead of OP 1. (yield 60%)
m/z：685.28(100.0％)，686.28(55.2％)，687.29(14.6％)，687.28(5.2％)，688.29(2.7％)，688.28(2.5％)
Synthesis of Compound 15
Figure GDA0003636234680000592
Compound 15 was synthesized in the same manner as compound 11 using OP5 instead of OP 1. (yield 55%)
m/z：645.25(100.0％)，646.25(52.0％)，647.26(12.9％)，647.24(4.5％)，648.25(2.4％)，648.26(2.2％)
Synthesis of Compound 16
Figure GDA0003636234680000593
Compound 16 was synthesized in the same manner as compound 11 using OP6 instead of OP 1. (yield 58%)
m/z：685.28(100.0％)，686.28(55.2％)，687.29(14.6％)，687.28(5.2％)，688.29(2.7％)，688.28(2.5％)
Synthesis of Compound 17
Figure GDA0003636234680000601
Compound 17 was synthesized in the same manner as compound 11 using OP7 instead of OP 1. (yield 54%)
m/z：645.25(100.0％)，646.25(52.0％)，647.26(12.9％)，647.24(4.5％)，648.25(2.4％)，648.26(2.2％)
Synthesis of Compound 18
Figure GDA0003636234680000602
Compound 18 was synthesized in the same manner as compound 11 using OP8 instead of OP 1. (yield 54%)
m/z：685.28(100.0％)，686.28(55.2％)，687.29(14.6％)，687.28(5.2％)，688.29(2.7％)，688.28(2.5％)
Synthesis of Compound 19
Figure GDA0003636234680000603
Compound 19 was synthesized in the same manner as compound 11 using OP9 instead of OP 1. (yield 50%)
m/z：645.25(100.0％)，646.25(52.0％)，647.26(12.9％)，647.24(4.5％)，648.25(2.4％)，648.26(2.2％)
Synthesis of Compound 20
Figure GDA0003636234680000611
Compound 20 was synthesized in the same manner as compound 11 using OP10 instead of OP 1. (yield 48%)
m/z：685.28(100.0％)，686.28(55.2％)，687.29(14.6％)，687.28(5.2％)，688.29(2.7％)，688.28(2.5％)
Synthesis of Compound 21
Figure GDA0003636234680000612
Compound 21 was synthesized in the same manner as compound 1 using OP11 instead of OP 1. (yield 63%)
m/z：717.30(100.0％)，718.31(58.9％)，719.31(17.2％)，720.31(3.3％)
Synthesis of Compound 22
Figure GDA0003636234680000613
Compound 22 was synthesized in the same manner as compound 11 using OP11 instead of OP 1. (yield 67%)
m/z：733.28(100.0％)，734.28(59.6％)，735.29(17.0％)，735.28(5.2％)，736.29(3.4％)，736.28(2.7％)
Synthesis of Compound 23
Figure GDA0003636234680000621
In a round-bottomed flask, 8.8g of N- (9,9-dimethyl-9H-fluoren-2-yl) -9,9-diphenyl-9H-fluoren-2-amine (N- (9, 9-dimethyl-9H-fluoro-2-yl) -9, 9-diphenyl-9H-fluoro-2-amine), 3.0g of 3-bromobenzofuran (F: (R) (R))3-bromobenzofuran)、2.2g t-BuONa、0.6g Pd 2 (dba) 3 0.7ml of (t-Bu) 3 P was dissolved in 120ml of toluene, followed by stirring under reflux. The reaction was confirmed by TLC, and after addition of water, the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and recrystallized to obtain 6.84g of compound 23 (yield 70%).
m/z：641.27(100.0％)，642.28(52.4％)，643.28(13.6％)，644.28(2.4％)
Synthesis of Compound 24
Figure GDA0003636234680000622
Compound 24 was synthesized in the same manner as compound 23 using 3-bromobenzo [ b ] thiophene (3-bromobenzo [ b ] thiophene) in place of 3-bromobenzofuran (3-bromobenzofuran).
m/z：657.25(100.0％)，658.25(53.1％)，659.26(13.4％)，659.24(4.5％)，660.25(2.4％)，660.26(2.3％)
Manufacture of organic light-emitting element
An organic light emitting element was manufactured according to the structure described in fig. 1. The organic light-emitting element is formed by stacking an anode (hole injection electrode 11)/a hole injection layer 12/a hole transport layer 13/a light-emitting layer 14/an electron transport layer 15/a cathode (electron injection electrode 16) in this order from below.
The following materials were used for the hole injection layer 12, the hole transport layer 13, the light-emitting layer 14, and the electron transport layer 15 in the following examples and comparative examples.
Figure GDA0003636234680000631
Manufacture of organic light-emitting element
Example 1
Will be provided with
Figure GDA0003636234680000632
A glass substrate coated with Indium Tin Oxide (ITO) in a thick film was ultrasonically cleaned with distilled water. After the cleaning with the distilled water is finished,ultrasonic cleaning with solvent such as isopropanol, acetone, and methanol, drying, transferring to plasma cleaning machine, cleaning the substrate with oxygen plasma for 5 min, and making DNTPD as hole injection layer on the ITO substrate by thermal vacuum coater
Figure GDA0003636234680000633
Film of (2), Compound 1 as hole transport layer
Figure GDA0003636234680000634
The film of (1). Then, as the light-emitting layer, 3% of a dopant BD01 was doped into a host BH01 to produce
Figure GDA0003636234680000635
The film of (4). Then, as an electron transport layer, a film with ET 01: liq (1: 1) manufacture
Figure GDA0003636234680000636
After the film of (2), LiF is produced
Figure GDA0003636234680000637
Film of (2), aluminum (Al)
Figure GDA0003636234680000638
Sealing (Encapsulation) the element in a glove box to produce an organic light-emitting element.
Examples 2 to 24
An organic light-emitting element was fabricated by forming a hole-transporting layer using compounds 2 to 24, respectively, in the same manner as in example 1.
Comparative example 1
An element was produced in the same manner as in example 1 except that NPB was used instead of compound 1 to produce the hole transport layer.
Comparative examples 2 to 6
The same method was used to manufacture the element except that ref.1 to ref.5 were used instead of compound 1 to manufacture the hole transport layer of example 1.
Evaluation of organic light-emitting element Performance
The organic light emitting elements of examples and comparative examples were evaluated for their performance by measuring the luminance at the time of light emission using a konishii 2400 digital source meter (kiethly 2400 source measurement unit) after injecting electrons and holes and measuring the current density and luminance against the applied voltage under atmospheric conditions using a konica minolta (konica minolta) spectroradiometer (CS-2000), and the results are shown in table 1.
[ Table 1]
Figure GDA0003636234680000651
As shown in table 1, it was confirmed that the compound of the present invention has excellent physical properties in all respects as compared with comparative examples 1 to 6 when used as a hole transport layer. In particular, the same Ar was found in comparison with comparative examples 3 to 4 1 And Ar 2 It is found that, when the arylamine is substituted at the 3-position of benzofuran or benzothiophene, the arylamine can maintain LUMO which is easy for electromagnetic shielding, and has excellent molecular alignment and hole mobility in a thin film state, thereby greatly affecting the improvement of efficiency and lifetime, as compared with comparative examples 5 to 6.

Claims (5)

1. A compound represented by the following chemical formula 1:
chemical formula 1
Figure FDF0000016508670000011
In the above-mentioned formula, the compound of formula,
x is O or S, and X is O or S,
l is phenyl, biphenyl or terphenyl,
Ar 1 and Ar 2 Each independently is substituted or unsubstituted biphenyl, fluorene, dimethylfluorene, diphenylfluorene or spirobifluorene, and said Ar 1 And Ar 2 Is substituted or notA substituted fluorene having a group consisting of (a) and (b),
R 1 、R 2 、R 3 、R 4 and R 5 Each independently is hydrogen; deuterium; by deuterium, halogen, amino, cyano, nitro, C 1-30 Alkyl radical, C 1-30 Alkoxy radical, C 2-30 Alkenyl, silyl substituted or unsubstituted C 6-50 And (4) an aryl group.
2. The compound of claim 1, wherein said L, Ar 1 And Ar 2 No aromatic amine is included.
3. The compound according to claim 1, which is represented by any one of the following chemical formulas,
Figure FDF0000016508670000012
Figure FDF0000016508670000021
Figure FDF0000016508670000031
Figure FDF0000016508670000041
Figure FDF0000016508670000051
Figure FDF0000016508670000061
Figure FDF0000016508670000071
Figure FDF0000016508670000081
Figure FDF0000016508670000091
Figure FDF0000016508670000101
Figure FDF0000016508670000111
4. an organic light-emitting element comprising an anode, a cathode, and 1 or more organic layers between the two electrodes, wherein the organic layers contain the compound according to any one of claims 1 to 3.
5. The organic light-emitting element according to claim 4, wherein the organic layer contains the compound according to claim 1 as a hole-injecting substance or a hole-transporting substance.
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