CN116854597A - Organic compound and application thereof - Google Patents

Organic compound and application thereof Download PDF

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CN116854597A
CN116854597A CN202210298001.3A CN202210298001A CN116854597A CN 116854597 A CN116854597 A CN 116854597A CN 202210298001 A CN202210298001 A CN 202210298001A CN 116854597 A CN116854597 A CN 116854597A
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organic compound
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黄鑫鑫
曾礼昌
曲忠国
田月娥
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Beijing Eternal Material Technology Co Ltd
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    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
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    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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Abstract

The invention provides an organic compound and application thereof, wherein the compound has a structure shown in a formula (1), and when the compound is used as an organic electroluminescent device, particularly as a sub-barrier layer material, the transmission of carriers in a balance device can be improved, the luminous efficiency can be improved, and the luminous time can be prolonged.

Description

Organic compound and application thereof
Technical Field
The invention provides an organic compound, belongs to the technical field of organic luminescent materials, and also relates to application of the compound in an organic electroluminescent device.
Background
Optoelectronic devices based on organic materials have become increasingly popular in recent years. The inherent flexibility of organic materials makes them very suitable for fabrication on flexible substrates, which can be designed to produce aesthetically pleasing and cool optoelectronic products, as desired, with no comparable advantages over inorganic materials. Examples of such organic optoelectronic devices include Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like. Among them, OLED has been developed particularly rapidly, and has been commercially successful in the field of information display. OLED can provide three colors of red, green and blue with high saturation, and the full-color display device manufactured by the OLED does not need extra backlight source, and has the advantages of colorful, light, thin, soft and the like.
The OLED device core is a thin film structure containing a plurality of organic functional materials. Common functionalized organic materials are: a hole injecting material, a hole transporting material, a hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, a light emitting host material, a light emitting guest (dye), and the like. When energized, electrons and holes are injected, transported to the light emitting region, respectively, and recombined therein, thereby generating excitons and emitting light.
Various organic materials have been developed, and various peculiar device structures are combined, so that carrier mobility can be improved, carrier balance can be regulated, electroluminescent efficiency can be broken through, and device attenuation can be delayed. For quantum mechanical reasons, common fluorescent emitters emit light mainly using singlet excitons generated when electrons and holes are combined, and are still widely used in various OLED products. Some metal complexes, such as iridium complexes, can emit light using both triplet and singlet excitons, known as phosphorescent emitters, and can have energy conversion efficiencies up to four times greater than conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technique can achieve higher luminous efficiency by promoting transition of triplet excitons to singlet excitons, and still effectively utilizing triplet excitons without using a metal complex. The thermal excitation sensitized fluorescence (TASF) technology adopts a material with TADF property to sensitize the luminophor by means of energy transfer, and can also realize higher luminous efficiency.
As OLED products continue to enter the market, there is an increasing demand for the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, lifetime, cost, etc.
Therefore, there is a need in the art to develop an organic electroluminescent material capable of improving the luminous efficiency of the device, reducing the driving voltage, and prolonging the service life.
Disclosure of Invention
It is an object of the present invention to provide an organic compound, and more particularly, to provide an electron blocking layer material, which is applied to an organic electroluminescent device, can improve the luminous efficiency of the device, reduce the driving voltage, and can be used as an electron blocking layer material in the organic electroluminescent device.
The present invention provides an organic compound having a structure represented by formula (1):
Ar 1 、Ar 2 、Ar 3 each independently is one of a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C3-C30 heteroaryl; and when R1 is hydrogen, ar 2 With Ar 3 Not both unsubstituted phenyl;
L 1 、L 2 each independently selected from one of a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene;
R 1 、R 2 、R 3 、R 4 each independently represents a monosubstituted group linked by a single bond to a maximum allowable number of substituents, and R 1 、R 2 、R 3 、R 4 Is not connected with adjacent substituent groups;
R 1 、R 2 、R 3 、R 4 each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstitutedOne of C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
R 5 one selected from the group consisting of a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group;
the above substituted substituents are each independently selected from one or a combination of two of halogen, C1-C20 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl.
Further, the organic compound of the present invention has a structure represented by any one of formula (1-1), formula (1-2), formula (1-3) or formula (1-4):
wherein Ar is 1 、Ar 2 、Ar 3 、L 1 、L 2 、R 1 、R 2 、R 3 、R 4 、R 5 The limiting ranges of (a) are the same as those in the formula (1);
further, the structure is represented by the formula (1-1).
In the above general formula of the compounds of the invention, L 1 、L 2 Each independently selected from one of a single bond, a substituted or unsubstituted phenylene group; further, L 1 Selected from single bonds, and/or L 2 Selected from single bonds.
The above general formula of the compounds of the inventionWherein R is 1 、R 2 、R 3 、R 4 Each independently selected from one of hydrogen, C1-C10 chain alkyl, C6-C30 aryl and C3-C30 heteroaryl;
further, R 1 、R 2 、R 3 、R 4 Each independently selected from one of hydrogen, methyl, ethyl, propyl, tert-butyl, cyclopropyl, phenyl, naphthyl, anthryl, phenanthryl, biphenyl and carbazolyl; further, R 1 、R 2 、R 3 、R 4 Each independently selected from hydrogen or phenyl.
In the above general formula of the compounds of the invention, R 5 Is one of C1-C10 chain alkyl and C3-C20 cycloalkyl;
further, R 5 Is one of methyl, ethyl, propyl, tertiary butyl and cyclopropyl; further, R 5 Is R 5 Is methyl or ethyl.
Ar in the above formula of the compound of the present invention 3 Is phenyl or biphenyl; further, ar 3 Is biphenyl.
Alternatively, in the above formula of the compound of the present invention, ar 1 、Ar 2 、Ar 3 Each independently is any one of the following substituted or unsubstituted: phenyl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, benzofluorenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazinyl, triazolyl, pyridinyl, pyrimidinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzindazolyl, benzocarbazolyl, benzofurocarzolyl, benzothiocarbazolyl, indolocarbazolyl, azadibenzothiophenyl, azadibenzofuranyl, phenylamino, naphthylamino, or biphenylamino; further, ar 3 Is phenyl or biphenyl.
Alternatively, in the above formula of the compound of the present invention, ar 1 、Ar 2 、Ar 3 Each independently is any one of the following substituted or unsubstituted:
wherein the label represents a bond to the group; the substituents on each of the above substituted groups are each independently selected from one or a combination of two of halogen, C1-C10 straight or branched chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, cyano, amino, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl; further, ar3 is phenyl or biphenyl.
More preferably, in the above formula of the compounds of the present invention, ar 2 、Ar 3 Not both phenyl.
In the present specification, the "substituted or unsubstituted" group may be substituted with one substituent or may be substituted with a plurality of substituents, and when the number of substituents is plural, the substituents may be selected from different substituents, and the same meaning is given when the same expression mode is involved in the present invention, and the selection ranges of the substituents are all shown above and are not repeated.
In the present specification, the expression of Ca to Cb means that the group has a carbon number of a to b, and unless otherwise specified, in general, in the present specification, "each independently" means that the group has a plurality of subjects, and they may be the same or different from each other.
Heteroatoms in the present specification generally refer to atoms or groups of atoms selected from N, O, S, P, si and Se, preferably N, O, S.
In the present specification, unless otherwise specified, the expression of a chemical element generally includes the concept of isotopes having the same chemical properties, for example, the expression of "hydrogen (H)", and also includes the expression of isotopes having the same chemical properties 1 H (protium or H), 2 The concept of H (deuterium or D); carbon (C) then comprises 12 C、 13 C, etc., and are not described in detail.
In the present specification, examples of halogen include: fluorine, chlorine, bromine, iodine, and the like.
In the present specification, unless otherwise specified, both aryl and heteroaryl include cases of single rings and condensed rings.
In the present specification, the substituted or unsubstituted C6-C60 aryl group includes monocyclic aryl groups and condensed ring aryl groups, preferably C6-C30 aryl groups, and further preferably C6-C20 aryl groups. By monocyclic aryl is meant that the molecule contains at least one phenyl group, and when the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are linked by a single bond, such as, for example: phenyl, biphenyl, terphenyl, and the like. Specifically, the biphenyl group includes a 2-biphenyl group, a 3-biphenyl group, and a 4-biphenyl group; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl. Condensed ring aryl refers to a group in which at least two aromatic rings are contained in the molecule, and the aromatic rings are not independent of each other but share two adjacent carbon atoms condensed with each other. Exemplary are as follows: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthryl, triphenylenyl, pyrenyl, perylenyl,And a radical, a tetracenyl radical, a derivative thereof, and the like. The naphthyl comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. The derivative group of the fluorene is selected from 9, 9-dimethylfluorenyl, 9-diethyl fluorenyl, 9-dipropyl fluorenyl, 9-dibutyl fluorenyl 9, 9-dipentylfluorenyl, 9-dihexylfluorenyl, 9-diphenylfluorenyl, 9-dinaphthylfluorenyl, 9' -spirobifluorene, and benzofluorenyl.
The C3-C60 heteroaryl group mentioned in the present specification includes monocyclic heteroaryl groups and condensed ring heteroaryl groups, preferably C3-C30 heteroaryl groups, further preferably C4-C20 heteroaryl groups, and further preferably C5-C12 heteroaryl groups. Monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and are linked by a single bond, and examples of the monocyclic heteroaryl group include: furyl, thienyl, pyrrolyl, pyridyl, and the like. Condensed ring heteroaryl means a group in which at least one aromatic heterocyclic ring and one aromatic ring (aromatic heterocyclic ring or aromatic ring) are contained in a molecule and two adjacent atoms are fused together without being independent of each other. Examples of fused ring heteroaryl groups include: benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl, and the like.
Examples of the C6-C30 arylamino group mentioned in the present specification include: phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrylamino, biphenylamino, and the like.
Examples of the C3-C30 heteroarylamino group mentioned in the present specification include: pyridylamino, pyrimidinylamino, dibenzofuranylamino and the like.
In the present specification, the C1 to C36 linear or branched alkyl group, preferably C1 to C20 linear or branched alkyl group, more preferably C1 to C16 linear or branched alkyl group, still more preferably C1 to C10 linear or branched alkyl group, exemplarily includes but is not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl, n-decyl and the like.
In the present specification, the C3-C20 cycloalkyl group includes a monocycloalkyl group and a multicycloalkyl group; wherein, monocycloalkyl refers to an alkyl group having a single cyclic structure; polycycloalkyl refers to a structure in which two or more cycloalkyl groups are formed by sharing one or more ring carbon atoms; examples of the C3-C20 cycloalkyl group include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, and the like.
In the present specification, the C3 to C20 heterocycloalkyl group, further preferably a C3 to C10 heterocycloalkyl group, i.e., a group in which at least 1 carbon atom in the cycloalkyl group listed above is replaced with a heteroatom (e.g., O, S or N, etc.), illustratively includes but is not limited to: tetrahydropyrrolyl, tetrahydrofuranyl, tetrahydrothienyl, piperidinyl, dioxane, and the like.
In the present specification, examples of the C1-C10 alkoxy group which is preferably substituted or unsubstituted C1-C20 alkoxy group, and which is preferably substituted or unsubstituted C1-C10 alkoxy group, may be given as follows: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like are preferred, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy are more preferred.
In the present specification, the aryloxy group is a monovalent group composed of the above aryl group and oxygen, and the heteroaryloxy group is a monovalent group composed of the above heteroaryl group and oxygen. The C6-C30 arylamino groups illustratively include, but are not limited to: phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrylamino, biphenylamino, and the like. The C3-C30 heteroarylamino groups illustratively include, but are not limited to: pyridylamino, pyrimidinylamino, dibenzofuranylamino and the like.
The organic compound of the present invention preferably has any one of the structures shown by the following P1 to P456:
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it is a further object of the present invention to provide the use of a compound according to one of the objects, for use in an organic electroluminescent device, preferably as an electron blocking layer material for said organic electroluminescent device.
When the compound provided by the invention is used as an electron blocking layer material of an organic electroluminescent device, the luminous efficiency can be effectively improved, the driving voltage can be reduced, and the compound is especially suitable for being used as a red light electron blocking layer material.
A third object of the present invention is to provide an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer contains the compound of one of the objects;
preferably, the organic layer includes an electron blocking layer containing the compound of one of the purposes.
The compound of the invention can be applied to not only organic electroluminescent devices, but also other types of organic electronic devices, including organic field effect transistors, organic thin film solar cells, information tags, electronic artificial skin sheets, sheet scanners or electronic papers.
Specifically, another technical scheme of the invention provides an organic electroluminescent device, which comprises a substrate, and an anode layer, a plurality of luminous functional layers and a cathode layer which are sequentially formed on the substrate; the light-emitting functional layer comprises at least one of a hole injection layer, a hole transmission layer, a light-emitting layer, an electron blocking layer and an electron transmission layer, wherein the electron blocking layer contains at least one compound.
The invention also discloses a display screen or a display panel, wherein the display screen or the display panel adopts the organic electroluminescent device; preferably, the display screen or display panel is an OLED display.
The invention also discloses electronic equipment, wherein the electronic equipment is provided with a display screen or a display panel, and the display screen or the display panel adopts the organic electroluminescent device.
The specific reason why the organic compound of the present invention is suitable for use as an electron blocking layer material in an organic electroluminescent device, the excellent performance of such a compound is not clear, presumably the following:
the organic compound provided by the invention has a molecular structure, is a triarylamine compound containing specific groups, and has fluorene groups containing aryl groups and alkyl groups connected to the aromatic amine N, so that compared with a pure phenyl fluorene group or methyl fluorene group, the organic compound has better thermodynamic stability and better tolerance to electrons, and is beneficial to improving the mobility of charges, so that the injection and migration of holes are well balanced. Meanwhile, the compound is connected with aryl or heteroaryl groups at the ortho position of the benzene ring connected with the aromatic amine N, so that molecules have better planarity and aromaticity, the space structure of the compound is more compact, the film stacking morphology is better, and the improvement of the photoelectric property of the device and the extension of the service life of the device are facilitated. In a preferred case, the LUMO/HOMO energy level of the material can be optimized by further adjusting groups at other sites, so that the material with better performance can be obtained. In summary, when the compound is applied to an organic electroluminescent device, particularly as an electron blocking layer material and/or a hole transport layer material, the efficiency and stability of the device can be effectively improved, the service life can be prolonged, the voltage and energy consumption can be reduced, and a better luminescent effect can be achieved.
In addition, the preparation process of the compound is simple and easy to implement, raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
It should be noted that the possible actions of the individual groups/features are described separately in the present invention for convenience of explanation, but this does not mean that the groups/features are acting in isolation. In fact, the reason for obtaining good properties is essentially an optimal combination of the whole molecule, as a result of the synergy between the individual groups, rather than the effect of a single group.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
The representative synthetic routes for the compounds of formula I of the present invention are as follows:
wherein Ar1 to Ar3, L1 to L2 and R1 to R5 have the same meaning as the symbols in the formula I; pd (PPh) 3 ) 4 Represents tetrakis (triphenylphosphine palladium), pd 2 (dba) 3 Represents tris (dibenzyl acetone) dipalladium (0), IPr.HCl represents 1, 3-bis (2, 6-diisopropylphenyl) imidazolyl chloride, naOBu-t represents sodium tert-butoxide, (t-Bu) 3 P represents tri-tert-butylphosphine. The preparation of the compounds of formula I according to the present invention includes, but is not limited to, the above-described methods, and the compounds of formula I synthesized by one skilled in the art using other methods are also within the scope of the present invention.
More specifically, the present invention provides, by way of example, a specific synthetic method for representative compounds, and solvents and reagents used in the following synthetic examples, all of which can be purchased or customized from the domestic chemical product market. In addition, the person skilled in the art can synthesize the compounds by known methods.
Synthesis example 1: synthesis of Compound P1
Synthesis of P1-1
In a 500ml single-necked flask, 10.0g of M1, 10.4g of 2-bromo-9-methyl-9-phenylfluorene, 0.3g of tris (dibenzylideneacetone) dipalladium (i.e. Pd 2 (dba) 3 ) 0.3g of 1, 3-bis (2, 6-diisopropylphenyl) imidazole chloride (i.e. IPr. HCl), 8.97g of sodium tert-butoxide (i.e. NaOBu-t), 200ml of toluene, vacuum-pumping and nitrogen-changing for 3 times, and heating to 90 ℃ for reaction for 8 hours. After the reaction, the reaction was stopped and cooled to room temperature. The organic phase is filtered by a silica gel column, concentrated, added with ethanol for refluxing and stirring for 2 hours, cooled and filtered to obtain yellow powder, and then recrystallized twice by toluene/ethanol to obtain 11.6g of pure product.
M/Z theory: 575; M/Z actual measurement: 575.
synthesis of P1
In a 500ml single port flask, 11.6g of P1-1, 3.8g of bromobenzene, 0.2g of tris (dibenzylideneacetone) dipalladium (i.e., pd) 2 (dba) 3 ) 0.2ml of tri-tert-butylphosphine (i.e., t-Bu) 3 P), 5.8g of sodium tert-butoxide (namely NaOBu-t), 150ml of toluene, vacuumizing and nitrogen exchange are carried out for 3 times, and the reaction temperature is raised to 110 ℃ for reaction for 12 hours. After the reaction, the reaction was stopped and cooled to room temperature. The organic phase is filtered by a silica gel column, concentrated, added with ethanol, refluxed and stirred for 2 hours, cooled and filtered to obtain yellow powder, and then recrystallized twice by toluene/ethanol to obtain 6.3g of pure product.
M/Z theory: 651; M/Z actual measurement: 651.
synthesis example 2 Synthesis example 12
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Device embodiment
Description of the embodiments
The OLED includes a first electrode and a second electrode, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combinations thereof may be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant-containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as the compounds shown below HT-1 to HT-51; or any combination thereof.
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The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-51 described above, or one or more of the compounds HI-1-HI-3 described below; one or more compounds from HT-1 to HT-51 may also be used to dope one or more of HI-1-HI-3 described below.
The luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise Host materials (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light emitting layer may be a single color light emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent host material thereof may be selected from, but is not limited to, one or more combinations of BFH-1 to BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent dopant thereof may be selected from, but is not limited to, one or more combinations of BFD-1 through BFD-24 listed below.
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In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The light-emitting layer host material is selected from, but not limited to, one or more of PH-1 to PH-85.
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In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-47 listed below.
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In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of the RPD-1 through RPD-28 listed below.
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In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant may be selected from, but is not limited to, one or more combinations of YPD-1-YPD-11 listed below.
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single layer structure including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, combinations of one or more of ET-1 through ET-73 listed below.
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In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may employ, but is not limited to, one or more of the compounds ET-1 to ET-73 described above, or one or more of the compounds PH-1 to PH-46; mixtures of one or more compounds of ET-1 to ET-73 with one or more compounds of PH-1 to PH-46 may also be employed, but are not limited to.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following.
LiQ,LiF,NaCl,CsF,Li 2 O,Cs 2 CO 3 ,BaO,Na,Li,Ca，Mg，Yb。
The preparation process of the organic electroluminescent device in this embodiment is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
placing the above glass substrate with anode in vacuum cavity, and vacuumizing to 10 -5 Pa, vacuum thermal evaporation of 10nm HT-4:HI-3 (97/3,w/w) mixture as hole injection layer, 60nm compound HT-4 as hole transport layer, 60nm compound P1 as electron blocking layer, 40nm compound PH-36:RPD-11 (97/3,w/w) binary mixture as light emitting layer, 25nm compound ET-69:ET-57 (50/50, w/w) mixture as electron transport layer, 0.5nm LiF as electron injection layer, 150nm metallic aluminum as electron injection layer on the anode layer filmIs a cathode. The total evaporation rate of all organic layers and LiF was controlled at 0.1 nm/sec, and the evaporation rate of the metal electrode was controlled at 1 nm/sec.
Device examples 2-12 were fabricated in the same manner as in example 1, except that P1 in the electron blocking layer was replaced with P2, P14, P73, P125, P193, P145, P169, P236, P298, P403, P445, etc., respectively.
Device comparative examples 1-5 were fabricated in the same manner as device example 1 except that P1 in the light-emitting layer was replaced with CCP-1, CCP-2, CCP-3, CCP-4 and CCP-5, respectively.
Wherein CCP-1 refers to the synthetic method in CN109075261 a; CCP-2 refers to the synthetic method in CN104487541 a; CCP-3 refers to the synthetic method in CN112125873 a; CCP-4 refers to the synthetic method in CN109485577 a; CCP-5 can be synthesized by referring to CN110317139a, and the above synthesis method is not described here.
The organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in examples 1 to 12 and comparative examples 1 to 5 were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the luminance of the organic electroluminescent device was measured to reach 3000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at that time is the driving voltage; meanwhile, measuring the current density at the moment, wherein the ratio of the brightness to the current density is the current efficiency; lifetime LT98 is the time required for the device to decay to 98% of the original luminance at a constant current density of 50mA/cm 2. The LT98 lifetime of comparative example 1 was set to 1, and the LT98 lifetime of the other compounds were all relative to that of comparative example 1.
Table 1:
the results show that when the organic material provided by the invention is used for an electron blocking layer in an organic electroluminescent device, the brightness of the prepared device is 3000cd/m 2 When the current efficiency is up to 19cd/A, compared with comparative example 1, LT98 can be up to 1.2 times, and the compound of the invention proves that the current efficiency of the device is effectively improved, the service life of the device is prolonged, and the compound is an electron blocking layer material with better performance and suitable for red light devices.
Compared with the comparative examples 1, 2 and 3, the ortho-position and para-position of the benzene ring connected with N of the compound contain aryl or heteroaryl groups, and the aryl or heteroaryl groups are not benzene rings at the same time, so that molecules have better planarity and aromaticity, the mobility of charges is improved, and meanwhile, the compound has a more compact space structure, good film stacking morphology and good film forming property, and the service life of devices is prolonged; compared with comparative example 3, the compound 9-methyl-9-phenylfluorene contains no condensed group, which is more beneficial to hole injection and better blocking of electrons; the compound has better charge mobility and better balance between hole injection and migration compared with comparative example 4 compared with comparative example 5, wherein the 9-position of fluorenyl group connected with N contains both aryl group and alkyl group; compared with the compound 5, the compound has better thermodynamic stability and better tolerance to electrons. In conclusion, compared with the comparative example, the compound provided by the invention has better improvement of photoelectric property.
While the invention has been described in connection with the embodiments, it is not limited to the above embodiments, but it should be understood that various modifications and improvements can be made by those skilled in the art under the guidance of the inventive concept, and the scope of the invention is outlined in the appended claims.

Claims (12)

1. An organic compound, characterized in that the compound has a structure represented by formula (1):
Ar 1 、Ar 2 、Ar 3 each independently is one of a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C3-C30 heteroaryl; and when R1 is hydrogen, ar 2 With Ar 3 Not both unsubstituted phenyl;
L 1 、L 2 each independently selected from one of a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene;
R 1 、R 2 、R 3 、R 4 each independently represents a monosubstituted group linked by a single bond to a maximum allowable number of substituents, and R 1 、R 2 、R 3 、R 4 Is not connected with adjacent substituent groups;
R 1 、R 2 、R 3 、R 4 each independently selected from one of hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
R 5 one selected from the group consisting of a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group;
the above substituted substituents are each independently selected from one or a combination of two of halogen, C1-C20 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl.
2. The organic compound according to claim 1, which has a structure represented by any one of formula (1-1), formula (1-2), formula (1-3) or formula (1-4):
wherein Ar is 1 、Ar 2 、Ar 3 、L 1 、L 2 、R 1 、R 2 、R 3 、R 4 、R 5 The limiting ranges of (a) are the same as those in the formula (1);
further, the structure is represented by formula (1-1).
3. The organic compound according to claim 1 or 2, wherein L 1 、L 2 Each independently selected from one of a single bond, a substituted or unsubstituted phenylene group;
further, L 1 Selected from single bonds, and/or L 2 Selected from single bonds.
4. The organic compound according to claim 1 or 2, wherein R 1 、R 2 、R 3 、R 4 Each independently selected from one of hydrogen, C1-C10 chain alkyl, C6-C30 aryl and C3-C30 heteroaryl;
further, R 1 、R 2 、R 3 、R 4 Each independently selected from one of hydrogen, methyl, ethyl, propyl, tert-butyl, cyclopropyl, phenyl, naphthyl, anthryl, phenanthryl, biphenyl and carbazolyl;
further, R 1 、R 2 、R 3 、R 4 Each independently selected from hydrogen or phenyl.
5. The organic compound according to any one of claim 1, 2 or 4,characterized in that R 5 Is one of C1-C10 chain alkyl and C3-C20 cycloalkyl;
further, R 5 Is one of methyl, ethyl, propyl, tertiary butyl and cyclopropyl;
further, R 5 Is R 5 Is methyl or ethyl.
6. The organic compound according to claim 1 or 2, wherein Ar 3 Is phenyl or biphenyl;
further, ar 3 Is biphenyl.
7. The organic compound according to claim 1 or 2, wherein Ar 1 、Ar 2 、Ar 3 Each independently is any one of the following substituted or unsubstituted:
phenyl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, benzofluorenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazinyl, triazolyl, pyridinyl, pyrimidinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzindazolyl, benzocarbazolyl, benzofurocarzolyl, benzothiocarbazolyl, indolocarbazolyl, azadibenzothiophenyl, azadibenzofuranyl, phenylamino, naphthylamino, or biphenylamino;
further, ar 3 Is phenyl or biphenyl.
8. The organic compound according to claim 1 or 2, wherein Ar 1 、Ar 2 、Ar 3 Each independently is any one of the following substituted or unsubstituted:
wherein the label represents a bond to the group;
the substituents on each of the above substituted groups are each independently selected from one or a combination of two of halogen, C1-C10 straight or branched chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, cyano, amino, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl;
further, ar 3 Is phenyl or biphenyl.
9. The organic compound according to any one of claims 1, 2,6, 7 or 8, wherein Ar 2 、Ar 3 Not both phenyl.
10. The organic compound according to claim 1, having the structure shown below:
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11. use of a compound according to any one of claims 1 to 10 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, an illumination element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet scanner or electronic paper;
further, the application of the organic compound is as an electron blocking layer material in an organic electroluminescent device.
12. An organic electroluminescent device comprises a substrate, and an anode layer, a plurality of luminous functional layers and a cathode layer which are sequentially formed on the substrate; the light-emitting functional layer comprises at least one of an electron blocking layer, a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the electron blocking layer contains at least one compound of any one of 1-10.
CN202210298001.3A 2022-03-25 2022-03-25 Organic compound and application thereof Pending CN116854597A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114685411A (en) * 2020-12-25 2022-07-01 北京鼎材科技有限公司 Organic compound, application thereof and organic electroluminescent device

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114685411A (en) * 2020-12-25 2022-07-01 北京鼎材科技有限公司 Organic compound, application thereof and organic electroluminescent device

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