Light emitting material composition and use thereof

Abstract

The present application provides a light-emitting material composition and its application in an organic electroluminescent device. The composition comprises a light-emitting host material and a dopant material, the light-emitting host material comprises a nitrogen-containing polycyclic compound represented by H-L-Ar, and H has a structure represented by formula 1-1 or formula 1-2. The present application also provides an organic electroluminescent device prepared by using the composition, which has higher light-emitting efficiency compared with conventional organic electroluminescent devices.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials, and particularly to a composition comprising a nitrogen-containing polycyclic compound and an organic electroluminescent device comprising the composition. Background Technology

[0002] Electroluminescent display devices can be classified into inorganic electroluminescent display devices and organic electroluminescent display devices based on the different materials used to make the light-emitting layer. Compared with inorganic electroluminescent display devices, organic electroluminescent display devices have incomparable advantages, such as full-color emission in the visible spectrum, extremely high brightness, extremely low driving voltage, fast response time, and simple manufacturing process.

[0003] Research on organic electroluminescence began in the 1860s. Pope first achieved electroluminescence on anthracene single crystals, but the driving voltage was as high as 100V, resulting in very low quantum efficiency. In 1987, Tang and Van Slyke used a bilayer thin film structure with 8-hydroxyquinoline aluminum complex (Alq3) as the luminescent and electron transport layer and TAPC as the hole transport layer, and used ITO and Mg:Ag electrodes as the anode and cathode, respectively, to fabricate a high-brightness (>1000 cd / m²) electroluminescence. 2 High-efficiency (1.5 lm / W) green organic electroluminescent thin-film devices were developed, with driving voltages reduced to below 10V. In 1990, Burroughes et al. obtained blue-green light output with a quantum efficiency of 0.05% using polymer thin-film electroluminescent devices made of poly(p-phenylene styrene) (PPV), with a driving voltage of less than 14V. In 1991, Braun et al. used PPV derivatives to produce green and orange light output with a quantum efficiency of 1%, with a driving voltage of approximately 3V. These research advances immediately attracted widespread attention from scientists around the world, and research on organic electroluminescence was widely carried out globally, gradually beginning to enter the market.

[0004] Luminescent materials are divided into two groups based on their emission mechanism: fluorescent materials, which utilize only 25% of singlet excitons, and phosphorescent materials, which utilize triplet excitons. Phosphorescent materials have higher luminous efficiency than fluorescent materials because they can utilize 75% of triplet excitons and 25% of singlet excitons, thus achieving 100% IQE (Intensity Quotient Efficiency). Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triplet gaps, making it possible for excitons to return from the doublet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] The color of light emitted by an OLED can be achieved through the design of its light-emitting material structure. An OLED can include one or more light-emitting layers to achieve a desired spectrum. Green, yellow, and red OLEDs using phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from issues such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically employ a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness levels remains a problem.

[0006] Currently, organometallic complexes and organic electroluminescent devices with phosphorescence emission have been reported, but in many applications such as TVs and lighting equipment, the lifetime of OLEDs is insufficient, and higher efficiency OLEDs are still needed. Typically, the higher the brightness of an OLED, the shorter its lifetime. Therefore, there is a need to develop OLEDs with higher luminous efficiency or longer lifetime. Summary of the Invention

[0007] The purpose of this invention is to provide a luminescent material composition comprising a luminescent host material and a dopant material, which can be used to produce organic electroluminescent devices with higher luminous efficiency.

[0008] A first aspect of the present invention provides a luminescent material composition comprising a luminescent host material and a dopant material, wherein the luminescent host material comprises a nitrogen-containing polycyclic compound as shown in formula (1):

[0009] HL-Ar formula (1),

[0010] Wherein, H has a structure represented by Equation 1-1 or Equation 1-2:

[0011]

[0012] In Formulas 1-1 and 1-2, ring 1, ring 2 and ring 3 are each independently selected from carbon rings having 5-18 carbon atoms or heterocarbon rings having 3-18 carbon atoms;

[0013] R X Each can be used independently to indicate monosubstituted, polysubstituted, or unsubstituted.

[0014] A 1 and A 2 Each is independently selected from N and CR;

[0015] Z is selected from O, S, Se, NR N CR a R b and SiR a R b ;

[0016] L is selected from one or more combinations of single bond, substituted or unsubstituted aryl group having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl group having 3-30 carbon atoms;

[0017] Ar, R, R X R N R a and R b Each is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted groups having 2-20 carbon atoms. The group consists of one or more of the following: alkenyl, substituted or unsubstituted alkynyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl with 3-20 carbon atoms, substituted or unsubstituted arylsilyl with 6-20 carbon atoms, and substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, and phosphinyl groups with 0-20 carbon atoms.

[0018] R, R X R a and R b They can be arbitrarily connected to form a loop;

[0019] The asterisk (*) indicates the location where the L bond is formed.

[0020] According to some embodiments of the present invention, in formula 1-1 or 1-2, ring 1, ring 2 and ring 3 are each independently selected from a 5-membered carbon ring, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms.

[0021] According to some embodiments of the present invention, in formula 1-1 or 1-2, ring 1, ring 2 and ring 3 are each independently selected from a 5-membered carbon ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring.

[0022] According to some embodiments of the present invention, H is selected from structures represented by formulas 2-1 to 2-8:

[0023]

[0024] Among them, X 1 To X 9 Each is independently selected from N and CR X ;

[0025] Z and Y can be chosen freely from O, S, Se, and NR. N CR a R b and SiR a R b The group formed;

[0026] R, R X R N R a and R b Each is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted groups having 2-20 carbon atoms. The group comprises one or more of the following: alkenyl, substituted or unsubstituted alkynyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl with 3-20 carbon atoms, substituted or unsubstituted arylsilyl with 6-20 carbon atoms, and substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, and phosphinyl groups with 0-20 carbon atoms.

[0027] According to some embodiments of the present invention, in the structures represented by formulas 2-1 to 2-9, R, R X RN R a and R b Each is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, and phosphine groups having 0-20 carbon atoms, or one or more combinations thereof; wherein R, R X R a and R b They can be arbitrarily connected to form a ring.

[0028] According to some embodiments of the present invention, in the structures represented by formulas 2-1 to 2-9, R, R X R N R a and R b At least one of them is selected from deuterium, substituted or unsubstituted aryl group having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl group having 3-30 carbon atoms.

[0029] According to some embodiments of the present invention, in the structures represented by formulas 2-1 to 2-9, R, R X R N R a and R b At least one of them is selected from deuterium, phenyl, biphenyl, naphthyl or pyridyl.

[0030] According to some embodiments of the present invention, any two or more substituents R can optionally be linked to form a carbon ring having 5-18 carbon atoms, or a heterocyclic carbon ring having 3-18 carbon atoms; preferably, selected from 5-membered carbon rings, aromatic rings having 6-18 carbon atoms, or heteroaromatic rings having 3-18 carbon atoms; more preferably, selected from benzene rings, naphthalene rings, phenanthrene rings, pyridine rings, furan rings, thiophene rings, fluorene rings, silylfluorene rings, and combinations thereof.

[0031] According to some embodiments of the present invention, H is selected from the group consisting of the following structures:

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042] According to some embodiments of the present invention, the hydrogen in structures H-1 to H-280 may be partially or completely replaced by deuterium.

[0043] According to some embodiments of the present invention, the L is selected from one or more combinations of single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted pyrazinylene, substituted or unsubstituted furanylene, substituted or unsubstituted thiopheneylene, substituted or unsubstituted dibenzofuranylene, and substituted or unsubstituted dibenzothiopheneylene.

[0044] According to some embodiments of the present invention, L is selected from one or more combinations of single bond, phenylene, naphthylene, biphenylene, terphenylene, pyridylene, pyrimidinylene, pyrazinylene, furanylene, thiopheneylene, dibenzofuranylene, and dibenzothiopheneylene.

[0045] According to some embodiments of the present invention, the L is selected from the group consisting of the following structures:

[0046]

[0047]

[0048] Optionally, the hydrogen in the structures of L-0 to L-50 can be partially or completely replaced by deuterium;

[0049] In the structures L-0 to L-50, "*" indicates the position where the structure connects to the H structure in Formula 1. This indicates the position where the structure shown is connected to the Ar structure in Equation 1.

[0050] According to some embodiments of the present invention, the Ar is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted groups having 2 carbon atoms, and so on. Alkenyl groups with -20 carbon atoms, substituted or unsubstituted alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, and substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, and phosphinyl groups with 0-20 carbon atoms, or one or more combinations thereof.

[0051] According to some embodiments of the present invention, Ar is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted aralkyl groups having 7-20 carbon atoms, substituted or unsubstituted alkoxy groups having 1-10 carbon atoms, substituted or unsubstituted groups having 6- One or more combinations of aryloxy groups with 20 carbon atoms, substituted or unsubstituted alkenyl groups with 2-10 carbon atoms, substituted or unsubstituted alkynyl groups with 2-10 carbon atoms, substituted or unsubstituted aryl groups with 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-20 carbon atoms, substituted or unsubstituted alkoxyl groups with 3-10 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-10 carbon atoms, and substituted or unsubstituted amino groups with 0-10 carbon atoms.

[0052] According to some embodiments of the present invention, Ar is independently selected from hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalyl, substituted or unsubstituted benzoquinoxalyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinoxalyl, substituted or unsubstituted isoquinoline. The group consists of one or more combinations of linyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted benzopyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzoimidazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted benzofuranyl.

[0053] According to some embodiments of the present invention, each of the Ar structures is independently selected from the group consisting of the following structures:

[0054]

[0055]

[0056]

[0057]

[0058] Optionally, the hydrogen in the Ar-1 to Ar-106 structures can be partially or completely replaced by deuterium.

[0059] According to some embodiments of the present invention, in formula (1), H is selected from the group consisting of H-1 to H-280, L is selected from the group consisting of L-0 to L-50, and Ar is selected from the group consisting of Ar-1 to Ar-106, wherein, optionally, hydrogen in formula (1) is partially or completely replaced by deuterium.

[0060] According to some embodiments of the present invention, the compound represented by formula (1) is selected from the group consisting of compounds C1 to C1688 and the group consisting of compounds D1 to D1688, wherein compounds D1 to D1688 correspond to the structures obtained by partially or completely replacing the hydrogen in compounds C1 to C1688 with deuterium.

[0061] The specific structures of H, L and Ar in compounds C1 to C1688 are shown in Table 1.

[0062] Table 1

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083] According to some embodiments of the present invention, the doping material in the composition comprises a compound represented by formula (I):

[0084]

[0085] In some embodiments, in formula (I), M is a metal with an atomic weight greater than 40.

[0086] In some implementations, in formula (I), La is a second ligand.

[0087] In some implementations, in formula (I), m is the maximum coordination number of the metal M.

[0088] In some implementations, in formula (I), d is the engagement degree of La, and n is at least 1.

[0089] In some implementations, R1 in formula (I) is selected independently for each ligand and represents di, tri, tetra, penta-substituted or unsubstituted.

[0090] In some embodiments, in formula (I), each of R1 is independently selected from the group consisting of: hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; at least two of R1 are independently selected from alkyl, silyl, germanyl, cycloalkyl, and combinations thereof containing two to six carbons.

[0091] In some embodiments, in formula (I), R2 may represent mono-, di-, tri-, tetra-substituted or unsubstituted; and each of R2 is independently selected from the group consisting of: hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl and combinations thereof.

[0092] In some embodiments, R1 represents disubstituted. In some embodiments, R1 represents dialkyl substituted. In some embodiments, R1 represents silyl or germanyl substituted.

[0093] In some embodiments, the doped material comprises a compound represented by formula (II):

[0094]

[0095] In formula (II), R3 and R4 represent alkyl groups.

[0096] In some embodiments, the doped material comprises a compound represented by formula (Ⅲ):

[0097]

[0098] In some embodiments, R1 is independently selected from the group consisting of: CH(CH3)2, CH2CH(CH3)2, CH2C(CH3)3, cyclopentyl, cyclohexyl, ethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylgermanyl, triethylgermanyl, and triisopropylgermanyl.

[0099] In some implementations, M is Ir.

[0100] In some implementations, n is 2.

[0101] In some implementations, La is a monoanionic bidentate ligand.

[0102] In some implementations, La is Furthermore, Rx, Ry, and Rz are each independently selected from one or more combinations of hydrogen, tritium, halide, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, and phosphinyl.

[0103] In some embodiments, Rx, Ry, and Rz are independently selected from one or more combinations of alkyl, hydrogen, and tritium.

[0104] In some embodiments, Rz is hydrogen or tritium, and Rx and Ry are independently selected from one or more combinations of methyl, CH(CH3)2, and CH2CH(CH3)2.

[0105] In some embodiments, the doped material comprises a compound represented by formula (Ⅳ):

[0106]

[0107] In some embodiments, the compound of formula (I) is selected from one or more of compounds P-1 to P-124, and optionally, the hydrogen in compounds P-1 to P-124 is partially or completely replaced by deuterium.

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114] A second aspect of the present invention provides the use of the composition described in the first aspect of the present invention in an organic electroluminescent device.

[0115] Preferably, the composition is used as a luminescent material in the luminescent layer of an organic electroluminescent device.

[0116] A third aspect of the present invention provides an OLED light-emitting layer comprising the composition described in the first aspect of the present invention.

[0117] According to some embodiments of the present invention, the doping concentration of the dopant material in the composition in the host material is 2-10%, preferably 2-8%, and more preferably 2-5%. The device exhibits optimal performance when the doping concentration of the dopant material in the host material is 3%. The doping concentration is a mass percentage concentration.

[0118] A fourth aspect of the present invention provides an electroluminescent device comprising the light-emitting layer described in the third aspect of the present invention.

[0119] According to some embodiments of the present invention, the electroluminescent device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer is a light-emitting layer.

[0120] According to some embodiments of the present invention, the host material of the light-emitting layer comprises a compound represented by formula (1) in the composition described in the first aspect of the present invention, and the doping material of the light-emitting layer comprises compounds represented by formulas (I) to (IV) in the composition described in the first aspect of the present invention.

[0121] Preferably, the light-emitting device further includes one or more of the following: a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0122] A fifth aspect of the present invention provides a display device or lighting device comprising the electroluminescent device provided in the fourth aspect of the present invention.

[0123] The beneficial effects of the present invention are: by using a combination of a host material comprising a nitrogen-containing polycyclic compound and a dopant material as the luminescent material of the organic electroluminescent layer, the present invention can prepare an organic electroluminescent device, display device or lighting device with higher luminous efficiency and / or longer lifetime characteristics compared with conventional organic electroluminescent devices. Detailed Implementation

[0124] To make the objectives, technical solutions, and advantages of this invention clearer, the invention will be further described in detail below with reference to embodiments. The specific embodiments described herein are for illustrative purposes only and are not intended to limit the scope of the invention in any way.

[0125] definition

[0126] In the compositions mentioned in this invention, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the composition cannot connect to form a ring. In the compositions mentioned in this invention, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring, and can be an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0127] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:

[0128]

[0129] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:

[0130]

[0131] Furthermore, the statement that adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two substituents bonded to the carbon atom directly bonded to each other represents hydrogen, the second substituent bonds at the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0132]

[0133] In this invention, the term "organic electroluminescent material" refers to a material that can be used in organic electroluminescent devices and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, and so on.

[0134] Material synthesis examples:

[0135] The compounds represented by formula (1) according to the present invention can be prepared by synthetic methods known to those skilled in the art. For example, the compounds represented by formula (1) can be prepared by referring to the following reaction scheme, but are not limited thereto.

[0136] Synthesis Example 1: Synthesis of Compound C566

[0137] Step 1: Synthesis of C566-IM-1

[0138]

[0139] In a 2L dry round-bottom flask, SM2 (40g, 1.0 eq, 336.78 mmol), potassium carbonate (139.3g, 3.0 eq, 1010.34 mmol), and N,N-dimethylformamide (500 mL) were added sequentially. The mixture was reacted at room temperature for 10 minutes, followed by the addition of SM1 (100g, 1.0 eq, 336.78 mmol), and the reaction was continued at room temperature for 20 hours. After the reaction was complete, an appropriate amount of water was added, and the mixture was extracted with ethyl acetate to separate the organic phase. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid intermediate C566-IM-1 (107g, 95% yield).

[0140] Step 2: Synthesis of C566-IM-2

[0141]

[0142] In a dry 2L round-bottom flask, potassium tert-butoxide (14.73 g, 2.2 eq, 131.3 mmol), C566-IM-1 (20 g, 1.0 eq, 59.68 mmol), and copper sulfate (476 mg, 0.05 eq, 2.98 mmol) were added sequentially. Nitrogen gas was purged three times. Under nitrogen protection, 1.2 L of chlorobenzene was added, and the reaction was carried out at 90 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered through diatomaceous earth, and washed with an appropriate amount of ethyl acetate. The filtrate was concentrated and separated by column chromatography to obtain a white solid intermediate, C566-IM-2 (12 g, 98% yield).

[0143] Step 3: Synthesis of C566-IM-3

[0144]

[0145] In a 1 L dry round-bottom flask under nitrogen protection, C566-IM-2 (10 g, 1.0 eq, 48.26 mmol), SM3 (8.45 g, 1.0 eq, 48.26 mmol), cesium carbonate (47.17 g, 3.0 eq, 48.26 mmol), and 300 mL of N,N-dimethylacetamide were added sequentially. The mixture was heated to 140 °C and reacted for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, and an appropriate amount of water was added. The mixture was extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid intermediate C566-IM-3 (14 g, 80% yield).

[0146] Step 4: Synthesis of C566-IM-4

[0147]

[0148] In a 1L dry round-bottom flask under nitrogen protection, C566-IM-3 (10g, 1.0eq, 27.6mmol) and 200mL of ultra-dry tetrahydrofuran were added sequentially. The mixture was cooled to -78℃, and then n-butyllithium (2.5M, 12mL, 1.1eq, 30.36mmol) was added dropwise. The reaction was continued at this temperature for 1 hour. Then, triisopropyl borate (7.79g, 1.5eq, 41.4mmol) was added, and the mixture was slowly heated to room temperature and reacted overnight. Then, a suitable amount of dilute hydrochloric acid was added, and the mixture was stirred for another hour. Then, a suitable amount of water was added, and the mixture was extracted with ethyl acetate to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate, concentrated, and then slurried with a suitable amount of n-heptane. The mixture was filtered to obtain a white solid intermediate C566-IM-4 (7.2g, 80% yield).

[0149] Step 5: Synthesis of C566-IM-5

[0150]

[0151] In a dry 500 mL round-bottom flask, C566-IM-4 (7 g, 1.0 eq, 21.4 mmol), SM4 (5.06 g, 1.0 eq, 21.4 mmol), potassium carbonate (7.38 g, 2.5 eq, 53.5 mmol), and tetraphenylphosphine palladium (742 mg, 0.03 eq, 0.642 mmol) were added sequentially. The mixture was purged with nitrogen three times. Under nitrogen protection, 100 mL of toluene, 10 mL of ethanol, and 10 mL of water were added, and the mixture was heated to 95 °C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a yellow solid intermediate, C566-IM-5 (6.2 g, 66% yield).

[0152] Step 6: Synthesis of C566-IM-6

[0153]

[0154] In a dry 500 mL round-bottom flask under nitrogen protection, C566-IM-5 (6 g, 1.0 eq, 13.67 mmol), cesium carbonate (13.4 g, 3.0 eq, 41.01 mmol), palladium acetate (153 mg, 0.05 eq, 0.684 mmol), tricyclohexylphosphine tetrafluoroborate (503 mg, 0.1 eq, 1.367 mmol), and 100 mL of xylene were added sequentially. The mixture was heated to 150 °C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered through diatomaceous earth, and washed with a suitable amount of dichloromethane. The filtrate was concentrated and separated by column chromatography to obtain a yellow solid intermediate C566-IM-6 (5 g, 91% yield).

[0155] Step 7: Synthesis of C566-IM-7

[0156]

[0157] In a dry round-bottom flask under nitrogen protection, C566-IM-6 (5 g, 1.0 eq, 12.43 mmol), triphenylphosphine (9.78 g, 3.0 eq, 37.29 mmol), and 100 mL of o-dichlorobenzene were added sequentially. The mixture was heated to 150 °C and reacted for 12 hours. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and the product was separated by column chromatography to obtain a yellow solid intermediate C566-IM-7 (3.7 g, yield 80%).

[0158] Step 8: Synthesis of C566

[0159]

[0160] In a dry round-bottom flask under nitrogen protection, C566-IM-7 (3.7 g, 1.0 eq, 10 mmol), SM5 (3.93 g, 1.2 eq, 12 mmol), cesium carbonate (6.52 g, 2.0 eq, 20 mmol), and 100 mL of N,N-dimethylacetamide were added sequentially. The mixture was heated to 150 °C and reacted for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, and a suitable amount of water was added dropwise. A large amount of yellow solid precipitated. The crude product was filtered off and separated by column chromatography to obtain yellow solid C566 (5.15 g, yield 76%).

[0161] Synthesis Example 2: Synthesis of Compound C577

[0162] Step 1: Synthesis of C577-IM-1

[0163]

[0164] In a 1 L dry round-bottom flask, SM6 (25 g, 1.0 eq, 140.44 mmol), SM7 (42.6 g, 1.5 eq, 210.66 mmol), potassium carbonate (58.2 g, 3.0 eq, 421.32 mmol), and tetraphenylphosphine palladium (8.1 g, 0.05 eq, 7.02 mmol) were added sequentially. The mixture was purged with nitrogen three times. Under nitrogen protection, 300 mL of tetrahydrofuran and 100 mL of water were added, and the mixture was heated to 70 °C and reacted for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid C577-IM-1 (28.7 g, 80% yield).

[0165] Step 2: Synthesis of C577-IM-2

[0166]

[0167] In a dry 1L round-bottom flask under nitrogen protection, C577-IM-1 (20g, 1.0 eq, 78.34 mmol), triphenylphosphine (61.64g, 3.0 eq, 235.02 mmol), and 200 mL of o-dichlorobenzene were added sequentially, and the mixture was heated to 150 °C and reacted for 6 hours. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and the solid intermediate C577-IM-2 (14g, 80% yield) was obtained by column chromatography.

[0168] Step 3: Synthesis of C577-IM-3

[0169]

[0170] In a 1 L dry round-bottom flask under nitrogen protection, C577-IM-2 (14 g, 1.0 eq, 62.7 mmol), SM3 (11 g, 1.0 eq, 62.7 mmol), cesium carbonate (61.3 g, 3.0 eq, 188.1 mmol), and 300 mL of N,N-dimethylacetamide were added sequentially. The mixture was heated to 150 °C and reacted for 3 hours. After the reaction was complete, the mixture was cooled to room temperature, and an appropriate amount of water was added. The mixture was extracted with ethyl acetate to separate the organic phase. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid intermediate C577-IM-3 (19.7 g, yield 83%).

[0171] Step 4: Synthesis of C577-IM-4

[0172]

[0173] In a 1L dry round-bottom flask under nitrogen protection, C577-IM-3 (19g, 1.0eq, 50.23mmol) and 300mL of ultra-dry tetrahydrofuran were added sequentially. The mixture was cooled to -78℃, and then n-butyllithium (2.5M, 22mL, 1.1eq, 55.25mmol) was added dropwise. The reaction was continued at this temperature for 1 hour. Then, triisopropyl borate (14.17g, 1.5eq, 75.35mmol) was added, and the mixture was slowly heated to room temperature and reacted overnight. Then, a suitable amount of dilute hydrochloric acid was added, and the mixture was stirred for another hour. Then, a suitable amount of water was added, and the mixture was extracted with ethyl acetate to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate, concentrated, and then slurried with a suitable amount of n-heptane. The mixture was filtered to obtain a white solid intermediate C577-IM-4 (14g, yield 81%).

[0174] Step 5: Synthesis of C577-IM-5

[0175]

[0176] In a dry 500 mL round-bottom flask, C577-IM-4 (14 g, 1.0 eq, 40.79 mmol), SM4 (9.65 g, 1.0 eq, 40.79 mmol), potassium carbonate (14.1 g, 2.5 eq, 102 mmol), and tetraphenylphosphine palladium (1.4 g, 0.03 eq, 1.224 mmol) were added sequentially. Nitrogen gas was purged three times. Under nitrogen protection, 200 mL of toluene, 20 mL of ethanol, and 20 mL of water were added, and the mixture was heated to 95 °C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a yellow solid intermediate, C577-IM-5 (13 g, 70% yield).

[0177] Step 6: Synthesis of C577-IM-6

[0178]

[0179] In a dry 500 mL round-bottom flask under nitrogen protection, C577-IM-5 (13 g, 1.0 eq, 28.58 mmol), cesium carbonate (27.9 g, 3.0 eq, 85.74 mmol), palladium acetate (321 mg, 0.05 eq, 1.43 mmol), tricyclohexylphosphine tetrafluoroborate (1.05 g, 0.1 eq, 2.858 mmol), and 200 mL of xylene were added sequentially. The mixture was heated to 150 °C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered through diatomaceous earth, and washed with a suitable amount of dichloromethane. The filtrate was concentrated and separated by column chromatography to obtain a yellow solid intermediate C577-IM-6 (10.3 g, yield 86%).

[0180] Step 7: Synthesis of C577-IM-7

[0181]

[0182] In a dry round-bottom flask under nitrogen protection, C577-IM-6 (10 g, 1.0 eq, 24 mmol), triphenylphosphine (18.9 g, 3.0 eq, 72 mmol), and 200 mL of o-dichlorobenzene were added sequentially. The mixture was heated to 150 °C and reacted for 12 hours. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and the solution was separated by column chromatography to obtain a yellow solid intermediate C577-IM-7 (7 g, yield 75%).

[0183] Step 8: Synthesis of C577

[0184]

[0185] In a dry 2L round-bottom flask under nitrogen protection, C577-IM-7 (3g, 1.0eq, 7.763mmol), SM5 (3.05g, 1.2eq, 9.315mmol), cesium carbonate (5.06g, 2.0eq, 15.53mmol), and 100mL of N,N-dimethylacetamide were added sequentially. The mixture was heated to 150℃ and reacted for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, and a suitable amount of water was added dropwise. A large amount of yellow solid precipitated. The crude product was filtered off and separated by column chromatography to obtain yellow solid C577 (3.8g, 70% yield).

[0186] The compounds represented by formula (I) according to the present invention can be prepared by synthetic methods known to those skilled in the art. For example, the compounds represented by formula (I) can be prepared by referring to the following reaction scheme: Chinese Patent Application Publication No. CN103159798A, but are not limited thereto.

[0187] Synthesis Example 3: Synthesis of Compound P-3

[0188] The synthesis route is as follows:

[0189]

[0190] (1) Synthesis of N-(3,5-dichlorobenzyl)-2,2-diethoxyethylamine: 512 g (284 mmol) of 3,5-dichlorobenzaldehyde, 386 g (284 mmol) of 2,2-diethoxyethylamine, and 270 mL of toluene were placed in a 500 mL three-necked flask. The mixture was heated to reflux under N2 protection for 24 hours, and the aqueous byproduct was collected using a Dean-Stark apparatus. After evaporation of the solvent, 86 g (100%) of a pale yellow liquid was obtained. The product was confirmed by GC-MS and NMR and was used in the next step without further purification.

[0191] (2) Synthesis of 5,7-dichloroisoquinoline: Trifluoromethanesulfonic acid (15.83 g, 103 mmol) was loaded into a 100 mL three-necked flask equipped with a Dean-Stark apparatus and a feeding funnel. The trifluoromethanesulfonic acid was first heated to 120 °C, and N-(3,5-dichlorobenzylmethyl)-2,2-diethoxyethylamine (4 g, 13.78 mmol) dissolved in 4 mL of DCM was added dropwise to the acid. After the addition, the mixture was heated at 120 °C for 2 hours, then cooled to room temperature, and the reaction was quenched by adding 8 mL of MeOH. The reaction mixture was poured into an aqueous solution of ammonium hydroxide (120 mmol), prepared to be alkaline with another aqueous solution of ammonium hydroxide, and stirred and filtered. Distillation yielded a white solid (21 g, 77%). The product was characterized by GC and HPLC. In the same manner, a larger-scale reaction was carried out using 32.2 g of N-(3,5-dichlorobenzylmethyl)-2,2-diethoxyethylamine, and 16.5 g (75%) of product was obtained for the next step.

[0192] (3) Synthesis of 5,7-diisobutylisoquinoline: 5,7-dichloroisoquinoline (5.8 g, 29.3 mmol), isobutylboronic acid (8.96 g, 88 mmol), dicyclohexyl(2,6-dimethoxy-[11-biphenyl]-2-yl)phosphine (0.962 g, 2.34 mmol), Pd2(dba)3 (0.536 g, 0.586 mmol), K3PO4 (21.8 g, 103 mmol), 150 mL toluene, and 15 mL water were placed in a flask. The reaction mixture was purified by bubbling with N2 for 30 minutes, followed by heating to reflux overnight. GC-MS analysis indicated that the reaction was complete. Silica gel chromatography using 15% ethyl acetate (v / v) in hexane as eluent yielded 6.7 g (95%) of product.

[0193] (4) Synthesis of 1-(3,5-dimethylphenyl)-5,7-diisobutylisoquinoline: 5,7-diisobutylisoquinoline (7.4 g, 30.7 mmol) in 50 mL of anhydrous THF was added dropwise to (3,5-dimethylphenyl)magnesium bromide (100 mL, 50.0 mmol) at room temperature and stirred for 16 hours. The reaction mixture was then heated to reflux for 5 hours. GC and HPLC analysis indicated that the reaction was complete, but contained a small amount of reduction byproducts, which were converted to the desired product by treatment with DDQ in THF for several minutes. Water treatment yielded 6.5 g (61.4%) of the product.

[0194] (5) Synthesis of iridium dimer: 1-(3,5-dimethylphenyl)-5,7-diisobutylisoquinoline (6.0 g, 17.37 mmol), IrCl3·H2O (2.57 g, 6.95 mmol), 90 mL of 2-ethoxyethanol, and 30 mL of water were placed in a 250 mL flask. The reaction mixture was heated to reflux for 19 hours under nitrogen protection. After filtration and washing with methanol, 3.1 g (24.3%) of dimer was obtained, which could be used in the next step without further purification.

[0195] (6) Synthesis of compound P-3: 2-(3,5-dimethylphenyl)-5,7-diisobutylquinoline iridium dimer (1.5 g, 0.82 mmol), 2,4-pentanedione (1.63 g, 16.36 mmol), Na₂CO₃ (1.73 g, 16.36 mmol), and 2-ethoxyethanol (60 mL) were placed in a 250 °C flask and stirred at room temperature for 72 hours. The resulting precipitate was filtered and washed with methanol. Further purification was achieved by passing the solid through a silica gel stopper (pretreated with 15% triethylamine in hexane). 0.55 g (34.3%) of the product was obtained after treatment. The product was characterized by LC-MS.

[0196] Synthesis Example 4: Synthesis of Compound P-47

[0197] The synthesis route is as follows:

[0198]

[0199] (1) Synthesis of 4-chloro-2-methylbenzoyl chloride: Oxaloyl chloride (26.8 g, 258 mmol) was added dropwise to a mixture of 4-chloro-2-methylbenzoic acid (24.0 g, 141 mmol) in dichloromethane (20 mL) and dimethylformamide (4 mL) at room temperature. The reaction was stirred at room temperature for 2 hours. Hexane was added and the reaction mixture was concentrated to give 4-chloro-2-methylbenzoyl chloride (26.6 g, quantitative), which was used directly for the next step without purification.

[0200] (2) Synthesis of 4-chloro-2-methylbenzamide: 30% ammonium hydroxide (300 mL, 4.76 mol) was cooled in a salt ice bath. 4-chloro-2-methylbenzoyl chloride (26.4 g, 140 mmol) in tetrahydrofuran (150 mL) was added and stirred for 1 hour. Water was added. The crystals were filtered off and washed with water, then dried under vacuum to give 4-chloro-2-methylbenzamide (20.0 g, 84% yield).

[0201] (3) Synthesis of 4-chloro-N-((dimethylamino)methylene)-2-methylbenzamide: A mixture of 4-chloro-2-methylbenzamide (20.8 g, 123 mmol) and 1,1-dimethylmethylamine (17.5 g, 147 mmol) in tetrahydrofuran (250 mL) was refluxed for 2.5 h and then concentrated. The resulting crystals were ground in hexane and filtered to give 4-chloro-N-((dimethylamino)methylene)-2-methylbenzamide (25.7 g, 93% yield).

[0202] (4) Synthesis of 6-chloroisoquinoline-1-ol: A mixture of 4-chloro-N-((dimethylamino)methylene)-2-methylbenzamide (25.7 g, 114 mmol), sodium tert-butoxide (25.7 g, 267 mmol), and tetrahydrofuran (450 mL) was refluxed under N2 for 3 hours and then poured into water (1 L). The pH was adjusted to 4 with an aqueous HCl solution. The solid was filtered off, washed with water, and dried under vacuum to give 6-chloroisoquinoline-1-ol (14.7 g, yield 71.6%).

[0203] (5) Synthesis of 4,6-dichloroisoquinoline-1-ol: A mixture of 6-chloroisoquinoline-1-ol (13.5 g, 75 mmol) and acetonitrile (400 mL) was heated to reflux. N-chlorosuccinimide (10.57 g, 79 mmol) was added dropwise to acetonitrile (110 mL). The mixture was refluxed overnight. Crystals were filtered off. The filtrate was concentrated, and the resulting crystals were washed with water, combined with the above crystals, and dried under vacuum to give 4,6-dichloroisoquinoline-1-ol (14.2 g, 88% yield). It was used directly in the next step without analysis.

[0204] (6) Synthesis of 4,6-dichloroisoquinoline-1-yl trifluoromethanesulfonic acid: A mixture of 14.2 g (66.5 mmol), pyridine (10.8 mL, 133 mmol), and dichloromethane (200 mL) was cooled in an ice bath. Trifluoromethanesulfonic anhydride (22.4 mL, 133 mmol) was added dropwise. The mixture was stirred overnight at room temperature. Water was added and NaHCO3 (20 g) was added slowly. The organic layer was dried over Na2SO4, concentrated, and rapidly separated by silica gel chromatography (4:1 hexane:dichloromethane, v / v) to give 4,6-dichloroisoquinoline-1-yl trifluoromethanesulfonic acid (37 g, 16% yield).

[0205] (7) Synthesis of 4,6-dichloro-1-(3,5-dimethylphenyl)isoquinoline: A mixture of 4,6-dichloroisoquinoline-1-yl trifluoromethanesulfonate (4.0 g, 11.6 mmol), 3,5-dimethylphenylboronic acid (1.6 g, 10.8 g), Pd(PPh3)4 (0.67 g, 0.58 mmol), potassium carbonate (4.79 g, 34.7 mmol), toluene (100 mL), and water (10 mL) was purified with nitrogen and refluxed overnight. The concentrated toluene layer was separated by silica gel chromatography (2:1 hexane:dichloromethane, v / v) to give 4,6-dichloro-1-(3,5-dimethylphenyl)isoquinoline (3.0 g, 92% yield).

[0206] (8) Synthesis of 1-(3,5-dimethylphenyl)isoquinoline: A mixture of 4,6-dichloro-1-(3,5-dimethylphenyl)isoquinoline (3.2 g, 10.59 mmol), isobutylboronic acid (4.32 g, 42.4 mmol), Pd2(dba)3 (0.388 g, 0.424 mmol), dicyclohexyl(2,6-dimethoxy-[1,1'-biphenyl-1-2-yl)phosphine (0.696 g, 1.694 mmol), K3PO4·H2O (24.38 g, 106 mmol), toluene (133 mL) and water (11 mL) was purified with nitrogen for 30 minutes and refluxed overnight. The toluene layer was separated by silica gel chromatography (100% dichloromethane to 4:1 dichloromethane: ethyl acetate, v / v) to give 1-(3,5-dimethylphenyl)isoquinoline (3.3 g, 90% yield).

[0207] (9) Synthesis of 1-(,5-dimethylphenyl)isoquinoline iridium dimer: A mixture of 1-(3,5-dimethylphenyl)-4,6-diisobutylisoquinoline (3.3 g, 9.55 mmol), IrC13·3H2O (1.475 g, 3.98 mmol), 2-ethoxyethanol (45 mL) and water (15 mL) was refluxed overnight and then filtered and washed with methanol to give 1-(3,5-dimethylphenyl)isoquinoline iridium dimer (2.0 g, yield 54.8%).

[0208] (10) Synthesis of compound P-47: A mixture of 1-(3,5-dimethylphenyl)isoquinoline iridium dimer (0.8 g, 0.436 mmol), 2,6-dimethylheptane-3,5-dione (0.682 g, 4.36 mmol), potassium carbonate (0.603 g, 4.36 mmol), and 2-ethoxyethanol (60 mL) was stirred overnight at room temperature, filtered, washed with methanol, and separated by chromatography on silica gel (4:1 hexane:chloromethane, v / v silica gel pretreated with triethylamine). The residue was dissolved in dichloromethane and 2-propanol. Dichloromethane was removed on a rotary evaporator, and 0.60 g of crystals were obtained after filtration. It was confirmed by LC-MS.

[0209] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and they can obtain other compound structures of the present invention by improving it.

[0210] Device Example 1

[0211] First, the glass substrate, which has a 120 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate is dried in a nitrogen-filled glove box to remove moisture, and then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -8 In the case of Torr, The deposition rate is achieved sequentially on the ITO anode via thermal vacuum. Simultaneously, the deposited compounds HT and NDP-9 are used as a hole injection layer (HIL), with a thickness of [missing information]. Compound HT is used as a hole transport layer (HTL) with a thickness of [missing information]. Compound EB is used as an electron blocking layer (EBL) with a thickness of [missing information]. Then, the compound C566 of the present invention, as the main component, and compound P-3, as a dopant (doping concentration 3%), are co-deposited as an emissive layer (EML) with a thickness of [missing information]. Compound HB was used as the hole blocking layer (HBL), with a thickness of [missing information]. On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited as an electron transport layer (ETL) with a thickness of [missing information]. Finally, vapor deposition Thick 8-hydroxyquinoline-lithium (Liq) was used as the electron injection layer (EIL) and deposited by evaporation. Aluminum was used as the cathode. The device was then transferred back to the glove box and sealed with a glass cover to complete the OLED-1 device.

[0212] Device Examples 2-4

[0213] Following the above-described method for fabricating OLED-1 devices, devices OLED-2 to OLED-4 were fabricated by adjusting the doping concentration of the dopant material in the host material from 3% to 5%, 8%, and 10%, respectively.

[0214] Device Examples 5-13

[0215] Following the same steps as above, the host material C566 in the emissive layer (EML) was replaced with compounds C6, C286, C306, C479, C577, C760, C817, C924, and C1126 of the present invention, respectively. The dopant material P-3 in the emissive layer (EML) was replaced with compounds P-6, P-12, P-47, P-82, P-109, P-117, P-119, P-121, and P-123 of the present invention, respectively, to obtain the devices OLED-5 to OLED-13 provided by the present invention.

[0216] Device Comparison Examples 14-16

[0217] Following the same steps as above, compounds A, B, and C were used to replace the host material in the emissive layer (EML) to obtain comparative devices OLED-14 to OLED-16.

[0218] Device performance testing

[0219] The performance of the fabricated devices OLED-1 to OLED-4 was tested, and the results are detailed in Table 2 below.

[0220] Table 2

[0221]

[0222] Comparing the test results of the four light-emitting devices above, it can be seen that the OLED-1 light-emitting device has the best performance, that is, when the doping concentration is about 3%, the brightness is the highest and the efficiency is also the highest.

[0223] The detailed device layer structures and thicknesses in Examples 1, 5-13, and Comparative Examples 14-16 are shown in Table 3 below. The layers used are made of more than one material, obtained by doping different compounds in the stated weight ratios.

[0224] Table 3

[0225]

[0226]

[0227] The material structure used in the device is shown below:

[0228]

[0229] Table 3 lists the values ​​at 15 mA / cm 2 Under the conditions, the measured current efficiency (CE) and maximum wavelength (λ) max ) and external quantum efficiency (EQE). To better illustrate the data comparison, the CE and EQE data of Comparative Example 2 were set to 100%. The CE and EQE data of devices OLED-1, OLED-5 to OLED-13, OLED-14 and OLED-16 were converted relative to the corresponding data of OLED-14. The relevant data and conversion results are shown in Table 4.

[0230] Table 4

[0231]

[0232]

[0233] As shown in Table 4, the maximum wavelength of the comparative examples and the embodiments remained essentially unchanged. At 15 mA / cm² 2 At current density, the OLED-1, OLED-5 to OLED-13 devices made by using the composition provided by the present invention as a light-emitting material have a CE that is 8% to 12% higher than that of the comparative example OLED-14, and an EQE that is 5% to 10% higher than that of the comparative example OLED-14.

[0234] At 15mA / cm 2 At current density, the devices OLED-1, OLED-5 to OLED-13 made by using the composition of the present invention as the luminescent material have a CE that is 14% to 18% higher than that of the comparative example OLED-15, and an EQE that is 15% to 20% higher than that of the comparative example OLED-15, which is a very significant improvement.

[0235] At 15mA / cm 2At current density, the devices OLED-1, OLED-5 to OLED-13 made by using the composition of the present invention as the luminescent material showed a significant improvement in CE (electrical emission) of 7% to 11% compared to the comparative example OLED-13, and an improvement in EQE (electrical efficiency) of 8% to 13% compared to the comparative example OLED-13.

[0236] The data in Table 4 show that the organic electroluminescent device according to the present invention, which uses a combination of nitrogen-containing polycyclic compounds and doped materials as luminescent materials, has a higher luminous efficiency than conventional organic electroluminescent devices.

[0237] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.

Claims

1. A luminescent material composition comprising a luminescent host material and a dopant material, wherein the luminescent host material comprises a nitrogen-containing polycyclic compound of formula (1): HL-Ar formula (1) in, H is selected from the group consisting of the following structures: ， ， ， ； L is selected from structure L-0 or L-1: ， ； Among them, in the structures of L-0 and L-1, " "This indicates the position where the structure is connected to structure H in equation (1)," " indicates the position where the structure shown is connected to structure Ar in equation (1); Optionally, the hydrogen in the structure of L-1 may be partially or completely replaced by deuterium; Ar is selected from the group consisting of the following structures: ， ， ， ， ， ， ， ， ， Optionally, the hydrogen in the structures of Ar-1, Ar-24, Ar-32, Ar-74, Ar-83, Ar-84, Ar-85, Ar-86, and Ar-97 is partially or completely replaced by deuterium; The doped material includes the compound represented by formula (Ⅳ): Equation (Ⅳ) Wherein, R1 represents disubstituted, and R1 is independently selected from one or more combinations of alkyl, cyclopentyl, cyclohexyl, trimethylsilyl, and trimethylgermanyl groups containing two to six carbons; R2 indicates disubstituted; Each of R2 is independently selected from one or more combinations of alkyl and cycloalkyl groups; Rz is hydrogen or tritium, and Rx and Ry are independently selected from one or more combinations of methyl, CH(CH3)2, CH2CH(CH3)2, and CH(CH2CH3)2.

2. The luminescent material composition according to claim 1, characterized in that, In the structure H, some or all of the hydrogen is replaced by deuterium.

3. The luminescent material composition according to claim 1, characterized in that, The structure H is selected from the group consisting of the following structures: ， ， ， ， ， ， ， 。 4. The luminescent material composition according to claim 1, characterized in that, The nitrogen-containing polycyclic compounds represented by formula (1) are selected from the group consisting of the following structures and their components: 、 、 、 、 、 ； Optionally, the hydrogen in the nitrogen-containing polycyclic compound may be partially or completely replaced by deuterium.

5. The luminescent material composition according to claim 1, characterized in that, The doped material includes any one or more of the following compounds: ， ， ， ， ， ， ， ， ， ， Optionally, the hydrogen atoms in compounds P-3, P-6, P-12, P-47, P-82, P-109, P-117, P-119, P-121, and P-123 are partially or completely replaced by deuterium.

6. The use of the composition according to any one of claims 1 to 5 in an organic electroluminescent device, wherein the composition is used as a luminescent material in the luminescent layer of the organic electroluminescent device.

7. An OLED light-emitting layer comprising the light-emitting material composition according to any one of claims 1 to 5.

8. An organic electroluminescent device comprising the light-emitting layer as described in claim 7.

9. The organic electroluminescent device according to claim 8, characterized in that, The light-emitting device also includes an anode layer and a cathode layer.

10. The organic electroluminescent device according to claim 9, characterized in that, The light-emitting device further includes one or more of the following: a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

11. A display device or lighting device comprising the organic electroluminescent device of claim 10.

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