A deuterated composition, an organic electroluminescent device and its application

Abstract

This invention provides a deuterated composition, an organic electroluminescent device, and their applications. The deuterated composition comprises a first component and a second component, wherein the first component comprises at least two compounds, each having a structure as shown in Formula I. By designing the specific composition of the deuterated composition and using it as a material for the organic thin film layer of the organic electroluminescent device, this invention enables the organic electroluminescent device to exhibit lower driving voltage, higher current efficiency, and longer lifetime.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescent materials technology, specifically relating to a deuterated composition, an organic electroluminescent device, and its applications. Background Technology

[0002] Currently, organic light-emitting diode (OLED) display technology has been applied in smartphones, tablets, and other fields, and will further expand to large-size applications such as televisions. Over the past 30 years of development, various high-performance OLED materials have been developed. Through different designs of device structures and optimization of device lifespan, efficiency, and other performance characteristics, the commercialization of OLEDs has been accelerated, leading to their widespread application in display and lighting fields.

[0003] The selection of materials for the hole layer, emissive layer, and other organic functional layers also significantly impacts the device's current efficiency, driving voltage, and lifetime. Currently, the exploration of functional layer materials with higher performance is ongoing. Therefore, to meet the increasingly demanding requirements for OLED devices, the field urgently needs to develop a wider variety of higher-performance OLED materials. Summary of the Invention

[0004] To address the shortcomings of existing technologies, the present invention aims to provide a deuterated composition, an organic electroluminescent device, and its applications. The deuterated composition provided by the present invention can be used as a material for the organic thin film layer of an organic electroluminescent device, thereby improving the performance of the organic electroluminescent device.

[0005] To achieve this objective, the present invention adopts the following technical solution:

[0006] In a first aspect, the present invention provides a deuterated composition comprising a first component and a second component, wherein the first component comprises at least two compounds, each having a structure as shown in Formula I;

[0007]

[0008] In this case, one of X and Y is N, and the other is CR.

[0009] R is selected from any one of C6-C40 aryl and C3-C20 heteroaryl.

[0010] m and n are each independently selected from 0 or 1, and m and n are not both 0 at the same time.

[0011] When m is 0, Ar1 is selected from any one of C6-C40 aryl and C3-C20 heteroaryl.

[0012] When m is 1, Ar1 is selected from any one of single bond, C6-C40 arylene, and C3-C20 heteroarylene.

[0013] In the compounds with the structure shown in Formula I, each hydrogen atom may be independently substituted or not substituted by any one of -D, halogen, -CN, C6-C20 aryl, C6-C20 heteroaryl, C1-C6 straight-chain or branched alkyl, or C1-C6 alkoxy.

[0014] Compounds with the structure shown in Formula I satisfy at least one of the following conditions:

[0015] (1) The compound with the structure shown in Formula I does not contain deuterium atoms;

[0016] (2) In the compound with the structure shown in Formula I, All hydrogen atoms in the group are replaced by deuterium atoms;

[0017] (3) In the compound with the structure shown in Formula I, at least one hydrogen atom in Ar1 is replaced by a deuterium atom;

[0018] (4) In the compound with the structure shown in Formula I, for Group;

[0019] (5) At least one hydrogen atom in R is replaced by a deuterium atom;

[0020] (6) In the compound with the structure shown in Formula I, at least one hydrogen atom is replaced by any one of C6-C20 aryl or C6-C20 heteroaryl, and at least one hydrogen atom of C6-C20 aryl or C6-C20 heteroaryl is replaced by a deuterium atom;

[0021] (7) In the compound with the structure shown in Formula I, at least one hydrogen atom is replaced by any one of C1-C6 straight-chain or branched alkyl or C1-C6 alkoxy, and all hydrogen atoms in the C1-C6 straight-chain or branched alkyl or C1-C6 alkoxy are replaced by deuterium atoms.

[0022] In this context, dashed lines represent the bonding sites of functional groups.

[0023] The first component includes at least one compound of formula I that meets at least one of conditions (2) to (7).

[0024] In this invention, by designing the structure of the compound and the composition of the deuterated composition, the obtained deuterated composition can be used as a material for the organic thin film layer of organic electroluminescent devices, thereby improving the performance of organic electroluminescent devices.

[0025] It should be noted that if m is 0 and n is 1 in this invention, then Ar1 is selected from any one of C6-C40 aryl or C3-C20 heteroaryl; if Ar1 is a single bond, the two nitrogen-containing heterocycles are directly connected by a single bond; if both m and n are 1, then Ar1 is the corresponding disubstituted group, that is, Ar1 is selected from any one of C6-C40 arylene or C3-C20 heteroarylene.

[0026] In this invention, C6-C40 can be C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.

[0027] The C3-C20 can be C3, C6, C10, C12, C16, or C20, etc.

[0028] The C6-C20 can be C6, C8, C10, C12, C16, or C20, etc.

[0029] The C1-C6 can be C1, C2, C3, C4, C5, or C6.

[0030] In this invention, "D" represents a deuterium atom, and the same applies below.

[0031] In this invention, condition (3) is further preferably: when Ar1 in the compound with the structure shown in Formula I is selected from a single aromatic ring, such as phenylene or naphthylene, all hydrogen atoms on the single aromatic ring are replaced by deuterium atoms; when Ar1 in the compound with the structure shown in Formula I is composed of two or more aromatic rings, all hydrogen atoms on at least one aromatic ring are replaced by deuterium atoms, for example, when Ar1 is selected from biphenylene, all hydrogen atoms on at least one benzene ring are replaced by deuterium atoms; when Ar1 is selected from phenylene or naphthylene, all hydrogen atoms on the phenylene or naphthylene ring are replaced by deuterium atoms.

[0032] In this invention, condition (5) is further preferably: when R in the compound of Formula I is selected from a single aromatic ring, such as phenyl or naphthyl, all hydrogen atoms on the phenyl or naphthyl ring are replaced by deuterium atoms; when R in the compound of Formula I is composed of two or more aromatic rings, all hydrogen atoms on at least one aromatic ring are replaced by deuterium atoms, for example, when R is selected from biphenyl, all hydrogen atoms on at least one benzene ring are replaced by deuterium atoms; when R is selected from phenyl or naphthyl, all hydrogen atoms on the phenyl or naphthyl ring are replaced by deuterium atoms.

[0033] In this invention, condition (6) is further preferably: when the C6-C20 aryl group in the compound of Formula I is selected from a single aromatic ring, such as phenyl or naphthyl, all hydrogen atoms on the phenyl or naphthyl group are replaced by deuterium atoms; when the C6-C20 aromatic ring in the compound of Formula I is composed of two or more aryl groups, all hydrogen atoms on at least one aryl group are replaced by deuterium atoms, for example, when the C6-C20 aryl group is selected from biphenyl, all hydrogen atoms on at least one phenyl group are replaced by deuterium atoms; when the C6-C20 aryl group is selected from phenylnaphthalene, all hydrogen atoms on the phenyl and / or naphthyl groups are replaced by deuterium atoms.

[0034] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. The purpose and beneficial effects of the present invention can be better achieved and realized through the following preferred technical solutions.

[0035] As a preferred embodiment of the present invention, the C3-C20 heteroaryl group is selected from at least one of C3-C20 (e.g., C3, C6, C10, C12, C16, or C20) nitrogen-containing heteroaryl groups, dibenzofuranyl, dibenzothiophene, naphthobenzofuranyl, or dibenzothiophene.

[0036] As a preferred embodiment of the present invention, R is selected from any one of phenyl, biphenyl, naphthyl, phenanthryl, anthracene, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, triphenylene, fluoranyl, pyrene, perylene, spirofluorenyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, imidazolyl, benzimidazolyl, indo[a]fluorenyl, or hydrogenated benzirthalyl.

[0037] As a preferred embodiment of the present invention, R is selected from triphenylene, phenyl, naphthyl, diphenyl, 9,9-dimethylfluorenyl, fluoranyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, benzofluorenyl, spirofluorenyl, etc. Any one of them, where the dashed line represents the linking site of the group.

[0038] Preferably, when m is 0 in the compound with the structure shown in Formula I, Ar1 is selected from any one of phenyl, biphenyl, naphthyl, phenanthryl, anthracene, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, triphenylene, fluoranyl, pyrene, perylene, spirofluorenyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, imidazolyl, benzimidazolyl, indo[a]fluorenyl, or hydrogenated benzirthalyl.

[0039] Preferably, when m is 1 in the compound with the structure shown in Formula I, Ar1 is selected from any one of single bond, phenylene, biphenylene, naphthylene, phenanthrene, anthracene, fluorene, benzo[a]fluorene, dibenzo[a]fluorene, triphenylene, fluoranthylene, pyrene, perylene, spirofluorene, pyridylene, pyrazinyl, pyrimidinyl, triazineyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, imidazolyl, benzimidazolyl, indo[a]fluorene, or hydrogenated benzimidazolyl.

[0040] Preferably, when m is 0 in the compound with the structure shown in Formula I, Ar1 is selected from phenyl, naphthyl, diphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-diphenylfluorenyl, spirofluorenyl, triphenylene, fluoranyl, etc. Any one of them; where the dashed line represents the linking site of the group.

[0041] It should be noted that if m and n are both 1 in the compound with the structure shown in Formula I of this invention, then Ar1 is a disubstituent of the above-mentioned group.

[0042] As a preferred embodiment of the present invention, the C6-C20 aryl group is selected from at least one of phenyl, biphenyl, naphthyl, phenanthryl, anthracene, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, pyrene, perylene, indo[a]fluorenyl, or hydrogenated benzo[a]anthryl.

[0043] Preferably, the C1-C6 straight-chain or branched alkyl group is selected from at least one of methyl, ethyl, propyl or butyl.

[0044] Preferably, the C1-C6 alkoxy group is selected from at least one of methoxy, ethoxy, propoxy, or butoxy.

[0045] Preferably, in the compound with the structure shown in Formula I, each hydrogen atom is independently substituted or not substituted by any one of phenyl, methyl, tert-butyl, methoxy, -F, -CN, -D, diphenyl, 9,9-dimethylfluorenyl, dibenzothiophene, dibenzofuranyl, fluoranyl, triphenylene, or naphthyl.

[0046] As a preferred embodiment of the present invention, the compound with the structure shown in Formula I is selected from any one of the following substituted or unsubstituted compounds:

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056] The substitution refers to the replacement of at least one hydrogen atom in the above compound with a deuterium atom.

[0057] Specifically, the substitution refers to the substitution of the corresponding Ar1 or Ar2 in the above compounds. At least one hydrogen atom on an aryl group in the above substituents is completely replaced by a deuterium atom; and / or in the above compounds All the hydrogen atoms on it are replaced by deuterium atoms.

[0058] Preferably, the first component comprises at least two of the following compounds:

[0059]

[0060] It should be noted that the present invention does not impose any special restrictions on the preparation method of the compound with the structure shown in Formula I, and it can be prepared according to conventional technical means in the art.

[0061] As a preferred embodiment of the present invention, the second component includes compound A having the following structural formula:

[0062]

[0063] Among them, o, p, and q are each independently selected from 0 or 1.

[0064] When q is 1, Ar 001 Selected from any one of C6-C30 arylene or C6-C20 heteroarylene; when q is 0, Ar 001 It is selected from any one of C6-C30 aryl or C6-C20 heteroaryl.

[0065] Ar 002 Ar 003 Ar 102 Ar 103 Ar 202 Ar 203 Each is independently selected from any one of C6-C30 aryl or C6-C20 heteroaryl.

[0066] Ar 101 Ar201 Each is independently selected from any one of single bonds, C6-C30 arylene, or C6-C20 heteroarylene.

[0067] Ar 002 Ar 003 Ar can be connected into a ring using a single bond. 102 Ar 103 Ar can be connected into a ring using a single bond. 202 Ar 203 A ring can be formed by connecting with a single key; Ar 001 Ar 003 A ring can be formed by connecting with a single key; Ar 101 Ar 103 A ring can be formed by connecting with a single key; Ar 201 Ar 203 A ring can be formed by connecting the links with a single key.

[0068] Ring A and ring B are each independently selected from benzene rings or naphthalene rings.

[0069] In compound A, each hydrogen atom is independently prefixed with -F, -D, -CN, C6–C20 aryl, C1–C6 straight-chain or branched alkyl, or C1–C6 alkoxy. Any substitution or non-substitution in the group, * indicates the linkage site of the group.

[0070] X7 is selected from C or Si.

[0071] R 701 R 702 R 703 Each is independently selected from any one of C6-C20 aryl, C1-C6 straight-chain or branched alkyl groups, wherein R 701 R 702 R 703 When selected from C6 to C20 aryl groups, R 701 R 702 R 703 Any two elements can be linked together to form a ring using a single bond.

[0072] As a preferred technical solution of the present invention, the Ar 001At least one mono- or di-substituted group selected from the following groups: phenyl, biphenyl, naphthyl, anthracene, phenanthrene, fluorene, triphenylene, fluoranthyl, spirofluorene, dibenzofuran, dibenzothiophene, naphthobenzofuran, naphthobenzothiophene, dinaphthofuran, dinaphthothiophene, indolefluorene, indolocarbazolyl, indolecarbazolyl, terphenyl, tetraphenyl, imidazolyl, benzimidazolyl, pyridinyl, pyrimidinyl, piperazine, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzoquinoxalinyl, benzoquinazolinyl, azirphenanthrene, diazirphenanthrene, carbazolyl, benzocarbazolyl, naphthocarbazolyl, dibenzocarbazolyl, or triazinyl.

[0073] Preferably, the Ar 002 Ar 003 Ar 102 Ar 103 Ar 202 Ar 203 Each of the following is independently selected from any one or a combination of at least two of the following: phenyl, biphenyl, naphthyl, anthracene, phenanthryl, fluorenyl, triphenylene, fluoranyl, spirofluorenyl, dibenzofuranyl, dibenzothiopheneyl, naphthobenzofuran, naphthobenzothiophene, dinaphthofuran, dinaphthothiophene, indole-fluorenyl, indolocarbazoyl, indole-carbazoyl, terphenyl, tetraphenyl, imidazoyl, benzimidazolyl, pyridyl, pyrimidinyl, piperazine, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzoquinoxalinyl, benzoquinazolinyl, azirphenyl, diazirphenyl, carbazoyl, benzocarbazoyl, naphthocarbazoyl, dibenzocarbazoyl, or triazinyl.

[0074] Preferably, the Ar 101 Ar 201 Each is independently selected from single bonds, phenylene, biphenylene, naphthylene, anthracene, phenanthrene, fluorene, triphenylene, fluorenylene, spirofluorene, dibenzofuranyl, dibenzothiophene, naphthanobenzofuran, naphthanobenzothiophene, dinaphthanofuran, dinaphthiophene, indole-fluorene, indole-carbazoyl, indole-carbazoyl, terphenylene, tetraphenylene The group consisting of any one or at least two of the following: yl, imidazolyl, benzimidazolyl, pyridinyl, pyrimidinyl, piperazine, quinolinyl, isoquinolinyl, quinoxalinyl, quinoxalinyl, benzoquinoxalinyl, benzoquinoxalinyl, benzoquinoxalinyl, diazaphenyl, carbazolyl, benzocarbazolyl, naphthocarbazolyl, dibenzocarbazolyl, and triazine.

[0075] As a preferred technical solution of the present invention, the Ar 001The group is selected from any one of the following mono- or di-substituted groups: phenyl, diphenyl, triphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, quinoxaline, quinazoline, or triazine.

[0076] Preferably, the Ar 101 Ar 201 Each is independently selected from any one or a combination of at least two of the following: phenylene, diphenylene, terphenylene, naphthylene, dibenzofuranylene, dibenzothiophenylene, carbazoylene, quinoxaline, quinoxaline, and triazineylene.

[0077] Preferably, the Ar 002 Ar 003 Ar 103 Ar 102 Ar 202 Ar 203 Each is independently selected from any one or a combination of at least two of phenyl, diphenyl, triphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, quinoxaline, quinazoline, and triazine.

[0078] Preferably, one of ring A and ring B is a naphthalene ring.

[0079] Preferably, the C6-C20 aryl groups in compound A are selected from any one of phenyl, naphthyl, or biphenyl.

[0080] As a preferred embodiment of the present invention, compound A is selected from any one of the following substituted or unsubstituted compounds:

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093] The substitution refers to the replacement of at least one hydrogen atom in the above compound with a deuterium atom.

[0094] It should be noted that in the above structures, when ring A or ring B is a naphthalene ring, any C atom on the naphthalene ring that can participate in bonding can participate in bonding. Examples are given below for compounds with the following structural formulas: It includes, but is not limited to, the following structures:

[0095]

[0096] Preferably, compound A comprises the following compounds:

[0097]

[0098] It should be noted that the present invention does not impose any special restrictions on the preparation method of compound A, which can be prepared according to conventional techniques in the field.

[0099] In a second aspect, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode; the material of the organic thin film layer comprises the deuterated composition as described in the first aspect.

[0100] Preferably, the organic thin film layer comprises an electron transport layer, a light-emitting layer, a hole transport layer, and an electron blocking layer; the main material of the light-emitting layer comprises the deuterated composition as described in the first aspect.

[0101] As a preferred embodiment of the present invention, the organic electroluminescent device is a red-light organic electroluminescent device.

[0102] Preferably, the organic electroluminescent device is a red phosphorescent organic electroluminescent device.

[0103] Thirdly, the present invention provides a display device comprising the organic electroluminescent device as described in the second aspect.

[0104] Compared with the prior art, the present invention has the following beneficial effects:

[0105] In this invention, by designing the specific composition and structure of the deuterated composition, and further by selecting the joint use of deuterated compounds with specific structural formulas, and using this deuterated composition as the material for the organic thin film layer of the organic electroluminescent device, the organic electroluminescent device has a lower driving voltage, higher current efficiency and longer lifespan. Detailed Implementation

[0106] To facilitate understanding of the present invention, the following embodiments are provided. Those skilled in the art should understand that these embodiments are merely illustrative and should not be construed as limiting the scope of the invention.

[0107] Example 1

[0108]

[0109] 0.02 mol of material 2, 0.022 mol of material 1, tris(dibenzylacetone)palladium (4 mol%), tri-tert-butylphosphine (8 mol%), 0.06 mol of tert-butyloxide potassium, and 200 mL of xylene were added to a 500 mL three-necked flask. The mixture was heated to 120 °C under nitrogen protection and reacted for 12 h. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, and the mixture was separated. The organic layer was washed with water and dried with sodium sulfate. Palladium black was removed by column chromatography, and then recrystallized from toluene and ethanol to obtain 16.8 g of the compound.

[0110] The mass spectrometry data of compound 1 were analyzed, and the mass spectrum m / z was measured to be 499.20. Theoretical elemental content (%) C 36 H 17 D4N3: C, 86.55, N, 8.41; Measured elemental content (%): C, 86.56; N, 8.42.

[0111] Example 2

[0112]

[0113] 0.02 mol of material 3, 0.022 mol of material 1, tris(dibenzylacetone)palladium (4 mol%), tri-tert-butylphosphine (8 mol%), 0.06 mol of potassium tert-butyloxide, and 200 mL of xylene were added to a 500 mL three-necked flask. The mixture was heated to 120 °C under nitrogen protection and reacted for 12 h. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, and the mixture was separated. The organic layer was washed with water and dried with sodium sulfate. Palladium black was removed by column chromatography, and then recrystallized from toluene and ethanol to obtain 9.5 g of compound 2H.

[0114] Mass spectrometry data of compound 2H were measured, with a m / z of 621.22. Theoretical elemental composition (%) C 46 H 27 N3: C, 88.86; H, 4.38; N, 6.76; Measured element content (%): C, 88.87; H, 4.36; N, 6.77.

[0115] Example 3

[0116]

[0117] 0.02 mol 2-A0, 0.022 mol p-chlorophenylboronic acid, tetra(triphenylphosphine)palladium (5 mol%), 0.03 mol potassium carbonate, 10 mL toluene, 10 mL ethanol, and 10 mL water were added to a 50 mL three-necked flask. The mixture was heated to 78 °C and reacted for 12 h under nitrogen protection. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, and the mixture was separated. The organic layer was washed with water and dried with sodium sulfate. Palladium black was removed by column chromatography, and then the mixture was recrystallized from toluene and ethanol to obtain compound 2-A1 2.9 g.

[0118] In a 50 mL three-necked flask, 0.016 mol 2-A1, 0.02 mol 2-naphthoic acid-D7, tris(dibenzylacetone)palladium (4 mol%), xphos (4.1 mol%), 0.024 mol potassium carbonate, 10 mL toluene, and 10 mL water were added. The mixture was heated to 110 °C under nitrogen protection and reacted for 12 h. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, and the mixture was separated. The organic layer was washed with water and dried with sodium sulfate. Palladium black was removed by column chromatography, and then the mixture was recrystallized from toluene and ethanol to obtain compound 2-A2 1.8 g.

[0119] 0.02 mol 2-A2, 0.022 mol material 1, tris(dibenzylacetone)palladium (4 mol%), tri-tert-butylphosphine (8 mol%), 0.06 mol tert-butyloxide potassium, and 200 mL xylene were added to a 500 mL three-necked flask. The mixture was heated to 120 °C under nitrogen protection and reacted for 12 h. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, and the mixture was separated. The organic layer was washed with water and dried with sodium sulfate. Palladium black was removed by column chromatography, and then the mixture was recrystallized from toluene and ethanol to obtain 28 g of the compound.

[0120] The mass spectrometry data of compound 2 were measured, and the m / z was 628.26. Theoretical elemental content (%) C 46 H 20 D7N3: C, 87.87; N, 6.68; Measured element content (%): C, 87.86; N, 6.68.

[0121] Example 4

[0122]

[0123] 0.02 mol of material 4, 0.022 mol of material 1, tris(dibenzylacetone)palladium (4 mol%), tri-tert-butylphosphine (8 mol%), 0.06 mol of tert-butyloxide potassium, and 200 mL of xylene were added to a 500 mL three-necked flask. The mixture was heated to 120 °C under nitrogen protection and reacted for 12 h. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, and the mixture was separated. The organic layer was washed with water and dried with sodium sulfate. Palladium black was removed by column chromatography, and then the mixture was recrystallized from toluene and ethanol to obtain 8.3 g of compound 3H.

[0124] Mass spectrometry data of compound 3H were measured, with a m / z of 585.18. Theoretical elemental composition (%) C 42 H 23 N3O: C, 86.13; H, 3.96; N, 7.17; Measured element content (%): C, 86.15; H, 3.94; N, 7.16.

[0125] Example 5

[0126]

[0127] 0.1 mol of material 1 and 180 g of deuterated benzene were added to a 500 mL three-necked flask, followed by the addition of 0.2 mol of aluminum trichloride. The reaction was carried out at room temperature for 48 h under nitrogen protection. The aluminum trichloride was filtered off, and the filtrate was quenched with ammonium chloride aqueous solution. The mixture was then separated, and the resulting organic phase was dried with sodium sulfate and passed through a silica gel column. The resulting chromatogram was concentrated to dryness and recrystallized with ethanol to obtain 25 g of compound 3-A1.

[0128] 0.02 mol of material 4, 0.022 mol of 3-Al, tris(dibenzylacetone)palladium (4 mol%), tri-tert-butylphosphine (8 mol%), 0.06 mol of potassium tert-butyloxide, and 200 mL of xylene were added to a 500 mL three-necked flask. The mixture was heated to 120 °C under nitrogen protection and reacted for 12 h. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, and the mixture was separated. The organic layer was washed with water and dried with sodium sulfate. Palladium black was removed by column chromatography, and then the mixture was recrystallized from toluene and ethanol to obtain 37 g of the compound.

[0129] Mass spectrometry data of compound 3 were analyzed, and the mass spectrum m / z was measured to be 597.26. Theoretical elemental content (%) C 42 H 11 D 12 N3O: C, 84.39; N, 7.03; Measured element content (%): C, 84.41; N, 7.02.

[0130] Other structures can be synthesized using similar methods.

[0131] The specific structures of the compounds used in the device embodiments and comparative examples of the present invention are shown below:

[0132]

[0133]

[0134] Device Example 1

[0135] This embodiment of the device provides an organic electroluminescent device, which uses the deuterated composition provided by the present invention as the red light host material in the organic electroluminescent device. The structure of the organic electroluminescent device is: ITO / HT-1 (20nm) / red light host material (35nm): RD1 [10%] / TPBI (10nm) / Alq3 (15nm) / LiF (0.5nm) / Al (150nm). Wherein "RD1 [10%]" refers to the doping ratio of red light dye, that is, the volume ratio of red light host material to RD1 is 90:10.

[0136] The organic electroluminescent device fabrication process is as follows: a glass plate coated with an ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol, baked in a clean environment until all moisture is removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0137] The glass substrate with the anode was placed in a vacuum chamber and evacuated to a vacuum level of 1×10⁻⁶. -5 ~9×10 -6 Pa, a hole transport layer HT-1 is vacuum-deposited on the above-mentioned anodic layer film at a deposition rate of 0.1 nm / s and a film thickness of 20 nm.

[0138] A red light-emitting host material and dye RD1 are vacuum-deposited on a hole transport layer to serve as the light-emitting layer of an organic electroluminescent device. The deposition rate is 0.1 nm / s, and the total film thickness is 35 nm. In this embodiment, two compounds of the first component and one compound of the second component are placed in different evaporation sources and heated. The heating rate is controlled so that the volume ratio of the three compounds deposited on the substrate is 1:1:1, serving as the red light-emitting host material. In this embodiment, the first component of the red light-emitting host material consists of compound 1H and compound 1, and the second component consists of compound H-7D.

[0139] Electron transport layers TPBI and Alq3 were sequentially vacuum-deposited on top of the light-emitting layer at a deposition rate of 0.1 nm / s, with film thicknesses of 10 nm and 15 nm, respectively.

[0140] 0.5 nm of LiF was vacuum-deposited on the electron transport layer, and 150 nm of Al was used as the electron injection layer and cathode.

[0141] Device Examples 2-13

[0142] Device Examples 2-13 each provide an organic electroluminescent device. The only difference between them and Device Example 1 is that the red light host material is different. The volume ratio of the two compounds in the first component of the red light host and the second component of the red light host deposited onto the substrate is 1:1:1 (see Table 1 for details). Other preparation steps and conditions are the same as those in Device Example 1.

[0143] Device Comparison Examples 1-6

[0144] Comparative Examples 1-6 each provide an organic electroluminescent device. The only difference between them and Device Example 1 is that the first component of the red light host material is a single compound (see Table 1 below). The other preparation steps and conditions are the same as those in Device Example 1.

[0145] Device Comparison Example 7

[0146] This invention provides an organic electroluminescent device, which differs from device example 1 only in that the red light host material is different, as detailed in Table 1 below. Other preparation steps and conditions are the same as those in device example 1.

[0147] Performance testing:

[0148] The brightness, driving voltage, current efficiency, and lifetime (LT90) of the fabricated organic electroluminescent device were measured using an OLED-1000 multi-channel accelerated aging lifetime and photochromic performance analysis system manufactured by Hangzhou Yuanfang. The lifetime test (LT90) refers to maintaining a constant current density (1000 cd / m²) at room temperature (25–27°C) while retaining the initial brightness. 2 The time required for the brightness to decrease to 90% of the initial brightness is denoted as LT90. The driving voltage, current efficiency, and LT90 are relative values ​​compared to Comparative Example 2. Detailed test data are shown in Table 1 below.

[0149] Table 1

[0150]

[0151]

[0152] As can be seen from the above, by designing the structure of the compound and the specific composition of the deuterated composition, and further by selecting the joint use of deuterated compounds with specific structural formulas, and using this deuterated composition as the material of the organic thin film layer of the organic electroluminescent device, the organic electroluminescent device has a lower driving voltage, higher current efficiency and longer lifespan.

[0153] Comparison of device example 1 with device comparative examples 1-2, device example 2 with device comparative examples 3-4, and device example 3 with device comparative examples 5-6 shows that the organic electroluminescent device prepared by the present invention using at least two compounds with specific structures as the first component of the red light host material has a lower driving voltage, higher current efficiency, and longer lifetime.

[0154] As can be seen from the relevant data of device examples 4-6, when the second component is compound H-9D2, the lifetime of the organic electroluminescent device can be further improved; when the second component is compound H-10, the current efficiency of the organic electroluminescent device can be further improved.

[0155] As can be seen from the comparison of relevant data between device examples 4-13 and device comparative example 7, by designing the first component and the second component together as the main red light material, the performance of organic electroluminescent devices can be effectively improved.

[0156] In summary, by designing the specific composition of the deuterated composition and using it as the material for the organic thin film layer of the organic electroluminescent device, the organic electroluminescent device exhibits lower driving voltage, higher current efficiency, and longer lifespan.

[0157] The applicant declares that the detailed process flow of this invention is illustrated by the above embodiments, but this invention is not limited to the above detailed process flow, that is, it does not mean that this invention must rely on the above detailed process flow to be implemented. Those skilled in the art should understand that any improvements to this invention, equivalent substitutions of raw materials for the product of this invention, addition of auxiliary components, and selection of specific methods, etc., all fall within the protection scope and disclosure scope of this invention.

Claims

1. A deuterated composition, characterized in that, The deuterated composition includes a first component and a second component, wherein the first component is selected from any one of the following combinations: compound 1 and compound 1H, compound 2 and compound 2H, and compound 3 and compound 3H; The second component includes any one of the following compounds: 。 2. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode; The material of the organic thin film layer includes the deuterated composition as described in claim 1.

3. The organic electroluminescent device according to claim 2, characterized in that, The organic thin film layer includes an electron transport layer, a light-emitting layer, a hole transport layer, and an electron blocking layer; the main material of the light-emitting layer includes the deuterated composition as described in claim 1.

4. The organic electroluminescent device according to claim 2, characterized in that, The organic electroluminescent device is a red-light organic electroluminescent device.

5. The organic electroluminescent device according to claim 4, characterized in that, The organic electroluminescent device is a red phosphorescent organic electroluminescent device.

6. A display device, characterized in that, The display device includes an organic electroluminescent device as described in any one of claims 2-5.

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