CN115340551A - Amino cyclic compound, organic electroluminescent material, and organic electroluminescent device - Google Patents

Abstract

The present invention relates to an amino cyclic compound, an organic electroluminescent material and an organic electroluminescent device. In particular, the structure of the amino cyclic compound is shown in formula 1, which provides a novel anti-triplet The hole-transporting material of dissociation energy has a triplet dissociation energy (TN-BDE) greater than 0.2eV hole-transporting material, and has good hole-transporting characteristics and electron tolerance; A hole transport material with state dissociation energy TN‑BDE>=0.4eV.

Description

Aminocyclic compound, organic electroluminescent material and organic electroluminescent device

technical field

The invention relates to the technical field of electroluminescent device materials, in particular to an amino cyclic compound with a specific arrangement of triplet stable groups, an organic electroluminescent material and an organic electroluminescent device containing the amino cyclic compound.

Background technique

Electronic devices containing organic, organometallic and/or polymeric semiconductors are becoming increasingly important and are used in many commercial products due to cost considerations and due to their performance. Examples here include organic-based charge-transport materials (e.g. triarylamine-based hole transporters) in copiers, organic or polymer light-emitting diodes (OLEDs or PLEDs) and in readout and display devices, or organic photoreceptors in copiers . Organic solar cell (O-SC), organic field effect transistor (O-FET), organic thin film transistor (O-TFT), organic integrated circuit (O-IC), organic optical amplifier and organic laser diode (O-laser) In a later stage of development and could be of great future significance.

In general, an OLED includes an anode, a cathode, and an organic light emitting unit. The last one contains several functional layers, such as hole or electron injection layers, hole or electron transport layers and organic light-emitting layers. Evaporation technology is the most commonly used technology for fabricating OLED devices. However, it presents a significant cost disadvantage, especially for large area devices, since the multi-stage vacuum process in a variety of different chambers is very expensive and must be controlled very precisely. In particular, the process should be able to be manufactured at low cost. At the same time, the process should be suitable for making very small cell structures, so that high-resolution screens can be obtained through this process.

Another problem is in particular the energy efficiency of organic electroluminescent devices to achieve the intended purpose. In the case of organic light-emitting diodes based on one or more OLED materials, their external quantum efficiency should be sufficiently high. In addition, the lowest possible voltage should be required to achieve the specified luminous density. More specifically, the direct connection to the emitting layer, especially the hole transport layer and the transition layer, has a great influence on the properties of the adjacent emitting layer. The quality of the hole injection layer directly connected to the hole transport layer also plays an important role in the performance of the OLED.

At present, in order to further improve the life and efficiency of the device, an auxiliary layer is added between the hole transport layer and the light-emitting layer, so that the holes transferred from the anode can move smoothly to the light-emitting layer, and can block the electrons transferred from the cathode. , to confine electrons in the light-emitting layer, reduce the potential barrier between the hole transport layer and the light-emitting layer, reduce the driving voltage of the organic electroluminescent device, and further increase the utilization rate of holes, thereby improving the luminous efficiency and life of the device . At present, the materials used as the luminescence auxiliary layer are limited, and the parameter requirements of the luminescence auxiliary layer have not yet been clarified. At the same time, the existing biscarbazole monomers have problems such as low synthesis yield and poor solubility during synthesis and use.

Contents of the invention

In order to solve the deficiencies in the prior art, the present invention proposes the concept of the triplet-state stability matrix of TSM-triplet state, which improves the anti-triplet state damage ability of the whole molecule, and simultaneously stabilizes the charge carriers in the excited state (Triplet-states Bond dissociation energy (TN-BDE)>0.2ev), and the addition of the triplet stabilizer significantly improves the physical and chemical properties of the compound, which is conducive to improving device efficiency and prolonging device life.

An object of the present invention is to provide a novel amine-containing compound. In particular, a novel hole transport material with very high resistance to triplet dissociation energy is provided. Furthermore, a hole-transporting material with a triplet dissociation energy (TN-BDE) greater than 0.2 eV is provided, and has good hole-transporting properties and electron tolerance. Furthermore, it is preferred to provide a hole transport material having a triplet dissociation energy TN-BDE>=0.4 eV.

Specifically, the present invention relates to an amino cyclic compound, the structure of which can be represented by Formula 1:

In the above formula 1,

N1 and N2 are the same or different from each other and represent nitrogen-containing ring structures;

o/q independently represent 0, 1, 2, 3 or 4;

p represents 0, 1 or 2;

R ₁ , R ₂ and R ₃ independently represent H, D, F, Cl, Br, I, N(R) ₂ , CN, NO ₂ , Si(R) ₃ , B(OR) ₂ , C(= O)R, P(=O)(R) ₂ , S(=O)R, S(=O) ₂ R, OSO ₂ R, straight-chain alkyl, alkoxy or Thioalkoxy groups, straight-chain alkenyl or alkynyl groups having 2 to 40 C atoms, branched or cyclic alkyl, alkenyl, alkynyl, alkane groups having 3 to 40 C atoms Oxy, alkylalkoxy or thioalkoxy groups, aryl or heteroaryl groups having 5 to 60 C atoms, each hydrogen of which may be replaced by one or more radicals R , where one or more non-adjacent CH2 groups can be represented by RC=CR, C≡C, Si(R) ₂ , Ge(R) ₂ , Sn(R) ₂ , C=O, C=S, C =Se, C=NR, P(=O)(R), SO, SO ₂ , NR, O, S or CONR instead;

L ₁ and L ₂ that are the same or different from each other represent a single bond or a divalent group, wherein the divalent group is selected from linear alkylene groups having 1 to 10 carbon atoms, linear alkylene groups having 3 to 10 A branched or cyclic alkylene group of carbon atoms, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may be substituted by one or more non-aromatic groups, NR, O or S;

Ar is selected from _a C6-C60 aryl group, a C3-C60 alicyclic group or a C1-C50 alkyl group, wherein each hydrogen in the above-mentioned groups can be replaced by one or more groups R, wherein One or more non-adjacent CH ₂ groups can be represented by RC=CR, C≡C, Si(R) ₂ , Ge(R) ₂ , Sn(R) ₂ , C=O, C=S, C= Se, C=NR, P(=O)(R), SO, SO ₂ , NR, O, S or CONR instead;

Ar ₂ is selected from a C6-C60 aryl group, a C5-C60 aromatic heterocyclic group containing at least one heteroatom, a C3-C60 alicyclic group or a C1-C50 alkyl group, wherein the above-mentioned groups Each hydrogen can be replaced by one or more groups R, where one or more non-adjacent CH ₂ groups can be replaced by RC=CR, C≡C, Si(R) ₂ , Ge(R) ₂ , Sn (R) ₂ , C=O, C=S, C=Se, C=NR, P(=O)(R), SO, SO ₂ , NR, O, S or CONR instead;

Wherein the rings A, B, C identically or differently represent an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, said aromatic or heteroaromatic ring system can be surrounded by one or more groups R replaces;

The radical R identifies H, D, F identically or differently, an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, wherein one or more H atoms may be replaced by F;

Two or more radicals R may form with one another a monocyclic or polycyclic aliphatic or aromatic ring system.

Further, the amino cyclic compound with the structure shown in Formula 1 can be represented by any one of the following formulas 1-1 to 1-19:

Ar ₁ and Ar ₂ are each selected from the structures represented by formula 3-1 to formula 3-9;

Among them, the rings F, G, H, and I each independently represent a condensed ring aryl group with a carbon number of C6 to C60, a condensed ring aryl group with a carbon number of C6 to C60 substituted by R, and a condensed ring aryl group with a carbon number of C5 to C60 Heterocondensed ring aryl group, heterofused ring aryl group with carbon atoms of C5-C60 substituted by R, cycloalkyl group with carbon atoms of C3-C30 or cycloalkyl group with carbon atoms of C3-C30 substituted by R , any one or more unconnected -CH2- in the cycloalkyl group is optionally replaced by -RC=CR-, -C≡C-, -Si(R)2-, -Ge(R)2-, - Sn(R)2-, -C=O-, -C=S-, -C=Se-, -C=NR-, -P(=O)(R)-, -SO-, -SO2-, -NR-, -O-, S- or -CONR-substitution;

R _c and R _d independently represent H, D, F, Cl, Br, I, N(R)2, CN, NO2, Si(R)3, B(OR)2, C(=O)R, P(=O)(R)2, S(=O)R, S(=O)2R, OSO2R, C1-C40 alkyl, R-substituted C1-C40 alkyl , an alkoxy group with C1-C40 carbon atoms, an alkoxy group with C1-C40 carbon atoms substituted by R, an alkoxy group with C1-C40 carbon atoms substituted by sulfur, and a C2-C40 carbon atom group Alkenyl, R-substituted alkenyl with C2-C40 carbons, C2-C40 alkynyl, R-substituted C2-C40 alkynyl, C6-C60 carbons fused ring aryl group, R-substituted fused ring aryl group with carbon atoms of C6-C60, hetero-fused ring aryl group with carbon atoms of C5-C60, or hetero-fused ring with carbon atoms of C5-C60 substituted by R Aryl, wherein any one or more unconnected -CH2- is optionally replaced by -RC=CR-, -C≡C-, -Si(R)2-, -Ge(R)2-, -Sn(R )2-, -C=O-, -C=S-, -C=Se-, -C=NR-, -P(=O)(R)-, -SO-, -SO2-, -NR- , -O-, S-, or -CONR-substitution.

Further, Ar ₁ is selected from groups represented by the following formula 31-1 to formula 31-88:

Ar ₂ is selected from groups represented by formula 32-1 to formula 32-178:

Further, the amino cyclic compound is represented by any one of the following formulas P1 to P9:

Wherein, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14 are independently selected from any of the following substituent Q1 to Q30 structures:

Further, the structure of the amino cyclic compound is formed by the combination of the following table:

Another object of the present invention is to provide a light-emitting element with high resistance to triplet dissociation energy and long life, and to provide a light-emitting element with high resistance to triplet dissociation energy and good luminous efficiency, and to provide A light-emitting element with a low driving voltage.

Yet another object of the present invention is to provide a light emitting element, a light emitting device, and an electronic device with high reliability, respectively, and to provide a light emitting element, a light emitting device, and an electronic device with low power consumption.

Suitable organic semiconductors according to the invention may preferably be hole-transport materials (HTM) and/or hole-injection materials (HIM). The hole injection material simplifies or facilitates the transfer of holes (ie, positive charges) from the anode into the organic layer. Hole transport materials are capable of transporting holes, ie positive charges, which are typically injected from the anode or an adjacent layer such as a hole injection layer.

Commonly preferred hole injection and/or hole transport materials include, for example, triarylamines, benzidines, tetraaryl-p-phenylenediamines, triarylphosphines, phenothiazines, thiophenes, pyrrole and furan derivatives and others with High HOMO (HOMO=highest occupied molecular orbital) O-, S- or N-containing heterocycle. Introduce a kind of electron-rich hole-transporting moieties into the material structure, which has better hole-transporting ability, can improve the overall HOMO and LUMO energy levels of the material, and has better hole-transporting efficiency or electron blocking ability.

According to the present invention, we are surprised to find that the main structure we designed is used as the core, and after connecting different substituents, it can have both the functions of a triplet stabilizer and a hole-transporting group. Use of the obtained compounds in organic electroluminescent devices results in them exhibiting various improved properties in terms of efficiency, operating voltage, lifetime, color coordinates and/or color purity, ie width of the emission band. In addition, the compounds have better solubility properties, can be processed in a very simple manner and have better thermal stability than existing materials. At the same time, due to the lower molecular weight, the compound has a lower sublimation temperature and is easier to produce on a large scale.

Description of drawings

FIG. 1 is a schematic diagram of a first embodiment of bottom emission of an organic electroluminescence device of the present invention.

Fig. 2 is a schematic diagram of the second embodiment of the top emission of the organic electroluminescence device of the present invention

Description of the accompanying drawings: 1-substrate, 2-first electrode, 3-hole injection, 41-hole transport, 42-electron blocking layer, 5-light-emitting layer, 6-electron transport layer, 7-electron injection layer, 8 - second electrode, 9 - light extraction layer.

Detailed ways

In order to understand the content of the present invention more clearly, the organic electroluminescent compound, the preparation method of the compound and the light-emitting characteristics of the device will be explained in detail with reference to examples. Various chemical reactions can be applied to the synthesis method of the compound of one embodiment of the present invention. The final target compound was obtained by two-step Hartwig-Buchwald coupling through the central compound SM-a. It should be noted, however, that the synthesis method of the compound of one embodiment of the present invention is not limited to the synthesis method described below. Subsequent syntheses were carried out in anhydrous solvents under a protective gas atmosphere unless otherwise stated. Solvents and reagents can be purchased from conventional reagent suppliers. The synthetic formula of the target compound is shown below:

Embodiment 1 prepares compound

SM-1 (25.38 g; 90 mmol), SM-2 (25.60 g; 100.0 mmol) and sodium tert-butoxide (10.1 g; 105 mmol) were first added to toluene (200 mL). Afterwards, palladium bisdibenzylideneacetone (57.5 mg; 0.1 mmol) and tri-tert-butylphosphine (40.4 mg; 0.2 mmol) were introduced, and the reaction mixture was stirred at reflux for 10 hours under nitrogen atmosphere. After cooling the mixture, it was adjusted to pH 7 with 1 mol/L dilute hydrochloric acid, and the organic phase was separated in a separatory funnel. Subsequently, the organic phase is filtered through column chromatography on silica gel as a solution in dichloromethane. The silica gel was washed twice with dichloromethane (100ml each), and the filtrate was dried _{over Na2SO4} , then concentrated to dryness. The crude product was recrystallized from ethyl acetate. The product obtained: 28.85g (63mmol); purity>98%.

Sub-1 (28.85 g; 63 mmol), SM-3 (9.8 g; 63 mmol) and sodium tert-butoxide (6.05 g; 63 mmol) were added to toluene (200 mL). Afterwards, palladium bisdibenzylideneacetone (36.22 mg; 0.063 mmol) and tri-tert-butylphosphine (25.45 mg; 0.126 mmol) were introduced, and the reaction mixture was stirred at reflux for 10 hours. After cooling the mixture, it was adjusted to pH 7 with 1 mol/L dilute hydrochloric acid, and the organic phase was separated in a separatory funnel. Subsequently, the organic phase was filtered through column chromatography on silica gel in the form of an ethyl acetate slurry. The silica gel was washed twice with ethyl acetate (100 ml each), and the filtrate was dried _{over Na2SO4} , then concentrated to dryness. The crude product was recrystallized from ethyl acetate. Product obtained: 25.3 g (47.37 mmol); purity >99%.

Example 2

SM-2 (25.38 g; 90 mmol), SM-5 (30.60 g; 100.0 mmol) and sodium tert-butoxide (10.1 g; 105 mmol) were first added to toluene (200 mL). Afterwards, palladium bisdibenzylideneacetone (57.5 mg; 0.1 mmol) and tri-tert-butylphosphine (40.4 mg; 0.2 mmol) were introduced, and the reaction mixture was stirred at reflux for 10 hours. After cooling the mixture, it was adjusted to pH 7 with 1 mol/L dilute hydrochloric acid, and the organic phase was separated in a separatory funnel. Subsequently, the organic phase was filtered through column chromatography on silica gel in the form of a toluene slurry. The silica gel was washed twice with toluene (100 ml each), and the filtrate was dried _{over Na2SO4} , then concentrated to dryness. The crude product was recrystallized from ethyl acetate. The product obtained: 35.56g (70.3mmol); purity>98%.

Sub-7 (35.56 g; 70.3 mmol), SM-5 (17.29 g; 70.3 mmol) and sodium tert-butoxide (7.0 g; 75.0 mmol) were first added to toluene (300 mL). Afterwards, palladium bisdibenzylideneacetone (40.25 mg; 0.07 mmol) and tri-tert-butylphosphine (28.28 mg; 0.14 mmol) were introduced, and the reaction mixture was stirred at reflux for 10 hours. After cooling the mixture, it was adjusted to pH 7 with 1 mol/L dilute hydrochloric acid, and the organic phase was separated in a separatory funnel. Subsequently, the organic phase was filtered through column chromatography on silica gel in the form of an ethyl acetate slurry. The silica gel was washed twice with ethyl acetate (150 ml each), and the filtrate was dried _{over Na2SO4} , then concentrated to dryness. The crude product was recrystallized from petroleum ether. Product obtained: 33.70 g (49.8 mmol); purity >99%.

Subsequent compounds can be prepared in an analogous manner. In this case, column chromatography can also be used; or other standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate ester, 1,4-dioxane recrystallization or thermal extraction; or use high boiling point substances such as dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N- Purify by recrystallization such as methylpyrrolidone. Yields typically range between 40% and 90%.

Synthesis of intermediate Sub:

Synthesis of the target compound:

Comparative example 1

Comparative compound 1 and comparative compound 2 were used as comparative examples of the present invention.

Device embodiment 1

The specific arrangement of the amino cyclic compound of the triplet stabilizing group according to the present invention makes an OLED device.

As shown in FIG. 1 and FIG. 2 , an organic electroluminescence device has a substrate 1 , an anode 2 , a cathode 8 , and a layer 3 - 7 arranged between the anode 2 and the cathode 8 . Among them, the electron transport layer 6 and the electron injection layer 7 are arranged between the cathode 8 and the light emitting layer 5 , and the hole injection layer 3 and the hole transport/luminescence auxiliary layer 4 are arranged between the light emitting layer 5 and the anode 2 . FIG. 2 is a schematic diagram of a second embodiment of the organic electroluminescence device of the present invention, which corresponds to the arrangement of top emission. Structurally, on the basis of the bottom emission arrangement in the first embodiment, a light extraction layer 9 is additionally provided on the top layer.

OLED Fabrication and Test Characterization

Device Comparison

The organic light-emitting device includes an anode, an organic material functional layer, a cathode, and an encapsulation layer sequentially arranged on a substrate; in the organic material functional layer, the hole injection layer formed on the anode, the A hole transport layer formed on the hole injection layer, a light emitting layer formed on the hole transport layer, an electron transport layer formed on the light emitting layer, a cathode formed on the electron transport layer.

The hole transport layer can be one or more layers, the light-emitting layer is composed of a host and a doped guest, and the host of the light-emitting layer can be composed of one molecular material or multiple molecular materials.

The molecular structure described in the present invention can be used in one or more layers of the above-mentioned organic electroluminescence device. More preferred hole injection layer, hole transport layer, luminescence assisting layer or host material for devices.

The anode in the embodiment adopts the anode material commonly used in this field, such as ITO, Ag or its multilayer structure. The hole injection unit adopts hole injection materials commonly used in this field, such as F4TCNQ, HATCN, NDP-9, etc. or doping thereof. The hole transport unit adopts hole transport materials commonly used in this field, such as PBPBA, TCTA and the like. The light-emitting unit adopts commonly used light-emitting materials in the field, for example, it can be composed of a host material and an emitting guest material, and the emitting guest material can be an organic material or a metal complex (such as metal Ir, Pt, etc.). The electron injection unit adopts electron injection materials commonly used in this field, such as Liq, LiF, Yb and the like. The cathode adopts common materials in this field, such as metal Al, Ag or metal mixture (Ag-doped Mg, Ag-doped Ca, etc.).

The electrode preparation method and the deposition method of each functional layer in this embodiment are conventional methods in the field, such as vacuum thermal evaporation or inkjet printing, etc., and will not be repeated here, only some process details and test methods in the preparation process The supplementary description of the method is as follows: the compound of the present invention uses the substance of the hole transport layer and adopts the usual method to produce an organic electroluminescent device. First, N1-(naphthalen-2-yl)-N4, N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl )-N1-phenylbenzene-1,4-diamine (hereinafter referred to as "2-TNATA") to form a hole injection layer, and then vacuum-deposit Comparative Compound 1 to a thickness of 60 nm on the hole injection layer to form a hole transport layer or transition layer. Next, on the above-mentioned hole transport layer or transition layer, the comparative compound 2 was vacuum-deposited with a thickness of 30 nm as the main body and tris(2-phenylpyridine)-iridium (hereinafter referred to as "Ir(ppy)3") or Bis( 2-methyldibenzo[f,h]quinoxaline)(acetylacetonate)iridium (hereinafter referred to as "Ir(MDQ)2acac") was used as a dopant, and a mixture doped at a weight ratio of 90:10 was vacuum-deposited to a thickness of 30nm. luminous layer. Next, ((1,1'-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato) aluminum (hereinafter referred to as "BAlq") was vacuum-deposited to a thickness of 10 nm on the above-mentioned light-emitting layer to form a void. As for the hole blocking layer, tris(8-quinolinol)aluminum (hereinafter, abbreviated as "Alq 3") was vacuum-deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Then, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then aluminum (Al) was deposited to a thickness of 150 nm to form a cathode, thereby producing an organic electroluminescent element.

The compound described in the example was prepared into an organic electroluminescent device by the above method.

Use as hole transport layer or luminescence auxiliary layer

Except that the inventive compound was used instead of the comparative compound 1 as the hole transport layer or other materials in the examples, the organic electroluminescent device was prepared in the same way as the above comparative example.

It is also possible to vacuum-deposit the compound invented in the example between the comparative compound 1 and the host material to partially replace the comparative compound 1 as a hole transport layer or a luminescence auxiliary layer, and other materials can be prepared in the same way as the above comparative example. Made of organic electroluminescent devices.

Used as the main material

An organic electroluminescent device was fabricated in the same manner as in the comparative example above, except that the inventive compound was used instead of the comparative compound 2 as the host material in the examples.

The device structures of various OLEDs are summarized in Table 1. The embodiment is compared with the device structures of Comparative Example 1 and Comparative Example 2 in the prior art.

Table 1 comparative example and embodiment device structure

The OLEDs were tested by standard methods. For this reason, the driving voltage, brightness, electroluminescent current efficiency (measured in cd/A) and external quantum efficiency (EQE, measured in percentage) of the electroluminescent device ^were determined at a current density of J=10mA/cm , which is calculated as a function of luminous density from the current/voltage/luminous density characteristic line (IVL characteristic line) exhibiting Lambertian emission characteristics, the luminous spectrum, and the CIE1931x and y color coordinates are calculated therefrom. The lifetime LT is defined as the time after which, when operating at a constant current J, the luminance drops from the initial luminous luminance L ₀ to a certain ratio L ₁ ; the expression J=50mA/cm ² and L ₁ =90% It means that when working at 50mA/cm ² , the luminous brightness drops to 90% of its initial value L ₀ after time LT, similarly, J=20mA/cm ² , L ₁ =80% means that at 20mA/cm ² , the luminous brightness drops to 80% of its initial value _L0 after time LT.

The data for various OLEDs are summarized in Table 2. The embodiment is compared with the parameters of the prior art Comparative Example 1 and Comparative Example 2, and the data of various OLEDs are shown.

Described embodiment carries out the test instrument and the method that OLED material and element are tested for performance as follows:

OLED component performance testing conditions:

Luminance and chromaticity coordinates: Tested using spectral scanner PhotoResearch PR-635;

Current density and lighting voltage: Tested with a digital source meter Keithley 2400;

Life test: life test device.

The performance test results of the obtained components are listed in Table 2.

Table 2 Component performance test results

As can be seen from the component performance test results in Table 2, the aminocyclic compound of the present invention can be used to prepare organic materials, and the luminous efficiency and service life of the devices prepared by using the organic materials have obvious advantages compared with the prior art Comparative Example 1 and Comparative Example 2. Improve, when the device works at 50mA/cm , the luminous brightness drops to 95% of its initial value _L0 , the time improves, and the ^compound of the present invention is used as the green light or red light hole transport layer, the device of the luminescence auxiliary layer Lifespan decay greatly slowed.

The above description is only a preferred embodiment of the present invention, but the scope of protection of the present invention is not limited thereto, any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope disclosed in the present invention etc. should be covered within the protection scope of the present invention. Therefore, the protection scope of the present invention should be determined by the protection scope of the claims.

Claims (9)

1. An aminocyclic compound, the structure of which is represented by formula 1:

in the above-mentioned formula 1, the,

n1 and N2, which may be the same or different from each other, represent a nitrogen-containing cyclic structure;

o/q independently represent 0, 1, 2, 3 or 4;

p represents 0, 1 or 2;

R ₁ 、R ₂ and R ₃ Independently of one another, represent H, D, F, cl, br, I, N (R) ₂ 、CN、NO ₂ 、Si(R) ₃ 、B(OR) ₂ 、C(＝O)R、P(＝O)(R) ₂ 、S(＝O)R、S(＝O) ₂ R、OSO ₂ R, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40C atoms, a linear alkenyl or alkynyl group having 2 to 40C atoms, a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40C atoms, an aryl or heteroaryl group having 5 to 60C atoms, each hydrogen of which may be substituted by one or more radicals R, wherein one or more non-adjacent CH2 groups may be substituted by RC = CR, C.ident.C, si (R) ₂ 、Ge(R) ₂ 、Sn(R) ₂ 、C＝O、C＝S、C＝Se、C＝NR、P(＝O)(R)、SO、SO ₂ NR, O, S or CONR;

L ₁ and L ₂ Are identical to or different from one another and are represented by a single bond or a divalent group, where the divalent group is selected from the group consisting of linear alkylene groups having from 1 to 10 carbon atoms, branched or cyclic alkylene groups having from 3 to 10 carbon atoms, aromatic or heteroaromatic ring systems having from 5 to 60 aromatic ring atoms and which may be substituted by one or more nonaromatic groups, NR, O or S;

Ar ₁ selected from a C6-C60 aryl group, a C3-C60 cycloaliphatic group or a C1-C50 alkyl group, wherein each hydrogen in the above groups may be substituted by one or more radicals R, wherein one or more non-adjacent CH groups ₂ The radicals may be substituted by RC = CR, C ≡ C, si (R) ₂ 、Ge(R) ₂ 、Sn(R) ₂ 、C＝O、C＝S、C＝Se、C＝NR、P(＝O)(R)、SO、SO ₂ NR, O, S or CONR;

Ar ₂ selected from a C6-C60 aryl group, a C5-C60 heteroaromatic group comprising at least one heteroatom, a C3-C60 alicyclic group or a C1-C50 alkyl group, wherein each hydrogen of the above groups may be substituted by one or more groups R, wherein one or more non-adjacent CH groups ₂ The radicals may be substituted by RC = CR, C ≡ C, si (R) ₂ 、Ge(R) ₂ 、Sn(R) ₂ 、C＝O、C＝S、C＝Se、C＝NR、P(＝O)(R)、SO、SO ₂ NR, O, S or CONR;

wherein rings a, B, C represent, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more groups R;

the radicals R, identically or differently, identify H, D, F, aliphatic, aromatic and/or heteroaromatic hydrocarbon radicals having 1 to 20C atoms, in which one or more H atoms may be replaced by F;

two or more radicals R may form a mono-or polycyclic, aliphatic or aromatic ring system with one another.

2. The aminocyclic compound according to claim 1, wherein the aminocyclic compound of formula 1 is represented by any one of the following formulae 1-1 to 1-19:

Ar ₁ 、Ar ₂ each selected from the group consisting of structures represented by formulas 3-1 to 3-9;

wherein each of rings F, G, H, and I independently represents a condensed ring aryl group having C6 to C60 carbon atoms, a condensed ring aryl group having C6 to C60 carbon atoms substituted with R, a hetero-condensed ring aryl group having C5 to C60 carbon atoms substituted with R, a cycloalkyl group having C3 to C30 carbon atoms, or a cycloalkyl group having C3 to C30 carbon atoms substituted with R, any one or more of the unconnected-CH 2-groups in the cycloalkyl groups being optionally substituted with-RC = CR-, -C.ident.C-, -Si (R) 2-, -Ge (R) 2-, -Sn (R) 2-, -C = O-, -C = S-, -C = Se-, -C = NR-, -P (= O) (R) -, -SO2-, -NR-, -O-, S-, or-CONR-;

R _c 、R _d each independently represents H, D, F, cl, br, I, N (R) 2, CN, NO2, si (R) 3, B (OR) 2, C (= O) R, P (= O) (R) 2, S (= O) R, S (= O) 2R, OSO2R, C1-C40 alkyl, R-substituted C1-C40 alkyl, C1-C40 alkoxy, R-substituted C1-C40 alkoxy, sulfur-substituted C1-C40 alkoxy, C2-C40 alkenyl, R-substituted C2-C40 alkenyl, C2-C40 alkynyl, R-substituted C2-C40 alkynyl, C2-C40 aryl OR C5-C5 heteroaryl, wherein any one OR more of the unconnected-CH 2-groups is optionally substituted with-RC = CR-, -C ≡ C-, -Si (R) 2-, -Ge (R) 2-, -Sn (R) 2-, -C = O-, -C = S-, -C = Se-, -C = NR-, -P (= O) (R) -, -SO2-, -NR-, -O-, S-, OR-CONR-.

3. The aminocyclic compound of claim 2, wherein Ar is Ar ₁ Selected from the group represented by the following formulae 31-1 to 31-88:

Ar ₂ selected from the group represented by formula 32-1 to formula 32-178:

4. the aminocyclic compound according to claim 3, characterized by being represented by any one of the following formulae P1 to P9:

wherein, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13 and R14 are mutually independent and selected from any one of the following substituent groups Q1 to Q30 structures:

5. the aminocycle compound of claim 4, wherein the structure of the aminocycle compound consists of a combination of the following tables:

6. an organic electroluminescent device comprising a first electrode, a second electrode, and a hole transport layer, an organic light emitting layer, and an electron transport layer interposed between the first electrode and the second electrode, wherein at least one of the hole transport layer, the organic light emitting layer, and the electron transport layer comprises one or more of the aminocyclics of any one of claims 1 to 5.

7. The organic electroluminescent device according to claim 6, wherein the amino cyclic compound according to any one of claims 1 to 5 is contained in the organic light-emitting layer.

8. The organic electroluminescent device of claim 7, the organic light-emitting layer contains a material selected from naphthalene, anthracene, pyrene, perylene, phenanthrene, fluoranthene, perylene, and perylene as a light-emitting host,

One or more of benzanthracene, pentacene, and derivatives thereof, and one or more aminocyclics according to any one of claims 1 to 5 as dopants.

9. An organic electroluminescent device, characterized in that it comprises the organic electroluminescent device according to any one of claims 6 to 8.

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