Deuterated composition and organic electroluminescent device

Abstract

The invention provides a deuterated composition and an organic electroluminescent device. The deuterated composition comprises a first component and a second component, the first component comprises a deuterated mixture obtained by deuteration reaction of a compound A; and the second component comprises a compound shown as a formula III. The specific composition of the deuterated composition is designed, the deuterated composition is used as the main body material of the light-emitting layer, and the prepared OLED device has the advantages of low driving voltage, high current efficiency and long service life.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a deuterated composition and an organic electroluminescent device. Background Art

[0002] Displays integrate electronics, communications and information processing technologies, and are considered another major development opportunity for the electronics industry after electronics and computers. Display technology and displays occupy a very important position in the development of information technology. Displays on televisions, computers, telephones and various instruments provide a large amount of information for people's daily lives and work. In recent years, new display technologies have become the focus of research, among which flat-panel displays have the advantages of light weight, low power consumption and easy portability, and have become a research hotspot.

[0003] Among the various flat panel displays currently available, liquid crystal displays (LCDs) play an important role. However, liquid crystal displays (LCDs) have many shortcomings: they do not emit light by themselves, but need to rely on light sources or ambient light, have viewing angle problems, have slow response speeds, and have low resolutions. Therefore, people have been looking for new flat panel display technologies. The phenomenon of organic electroluminescence was discovered as early as 1963, but it did not attract people's attention at the time. It was not until 1987 that the Tang research team of Kodak published a high-brightness, high-efficiency thin-film organic electroluminescent device (OLED) made of organic fluorescent materials and hole materials and driven by low DC voltage that the technology regained attention and opened up a new research field.

[0004] OLED has outstanding advantages, such as low power consumption, fast response speed, easy bending, wide viewing angle, large area display, full luminous colors, etc. It can be compatible with various existing standards and technologies to make low-cost light-emitting devices, showing broad application prospects in realizing color flat panel displays. In the past few decades, OLED, as a new display technology, has made great progress and has been widely used in the fields of flat panel displays, flexible displays, solid-state lighting and vehicle displays.

[0005] Therefore, developing more types of OLED materials with better performance to meet the needs of their use in high-performance OLED devices is a research focus in this field. Summary of the invention

[0006] In view of the shortcomings of the prior art, the present invention aims to provide a deuterated composition and an organic electroluminescent device. In the present invention, the specific composition of the deuterated composition is designed, and the deuterated composition is used as the main material of the light-emitting layer, and the prepared OLED device has a lower driving voltage, a higher current efficiency and a longer life.

[0007] To achieve this object, the present invention adopts the following technical solutions:

[0008] In a first aspect, the present invention provides a deuterated composition, the deuterated composition comprising a first component and a second component;

[0009] The first component includes a deuterated mixture obtained by deuterating compound A, wherein compound A has the following structure:

[0010]

[0011] Wherein, Ar1 and Ar2 are each independently selected from any one of phenyl, biphenyl or terphenyl;

[0012] The second component comprises a compound of formula III:

[0013]

[0014] Among them, Ar 11 ,Ar 12 ,Ar 13 Each independently selected from any one of phenyl, biphenyl or terphenyl;

[0015] The hydrogen atoms in the compound of formula III may each independently be replaced by a deuterium atom.

[0016] In the present invention, a deuterated mixture is obtained by subjecting a compound having a specific structure (compound A) to a deuterated reaction and a simple post-treatment. The deuterated mixture is used as the first component, and the compound of formula III is used as the second component. The prepared OLED light-emitting device has good comprehensive performance, low driving voltage, high current effect and long service life.

[0017] It should be noted that, in an organic reaction process, when there is no significant difference in the reactive sites on the reaction molecules, it is difficult to carry out a substitution reaction at a specific reaction site. Therefore, in the present invention, after deuteration reaction of compound A, a mixture (deuterated mixture) is obtained.

[0018] In the present invention, "D" represents a deuterium atom, and the same shall apply hereinafter.

[0019] As a preferred technical solution of the present invention, the deuteration reaction comprises the following steps:

[0020] In the presence of a catalyst, compound A is placed in D2O and a solvent to carry out a deuteration reaction to obtain the deuterated mixture.

[0021] As a preferred technical solution of the present invention, the catalyst is selected from any one or a combination of at least two of PdCl2, NiCl2, triphenylphosphine or tri-o-tolylphosphine; further preferably, it is any one or a combination of at least two of the combination of PdCl2 and NiCl2, the combination of PdCl2, NiCl2 and triphenylphosphine, and the combination of PdCl2, NiCl2 and tri-o-tolylphosphine.

[0022] Preferably, the ratio of the amount of PdCl2 and NiCl2 in the combination of PdCl2 and NiCl2 is (1-2):1 (for example, it can be 1:1, 1.2:1, 1.4:1, 1.6:1, 1.8:1 or 2:1, etc.), and more preferably 1:1.

[0023] Preferably, in the combination of PdCl2, NiCl2 and triphenylphosphine, the ratio of the amount of triphenylphosphine to the sum of the amounts of PdCl2 and NiCl2 is (1-3):1 (for example, it can be 1:1, 1.5:1, 2:1, 2.2:1, 2.5:1 or 3:1, etc.), and further preferably (2-2.5):1.

[0024] Preferably, in the combination of PdCl2, NiCl2 and tri-o-tolylphosphine, the ratio of the amount of tri-o-tolylphosphine to the sum of the amounts of PdCl2 and NiCl2 is (1-3):1 (for example, it can be 1:1, 1.5:1, 2:1, 2.2:1, 2.5:1 or 3:1, etc.), and further preferably is (2-2.2):1.

[0025] It should be noted that in the present invention, the deuteration reaction is carried out in the presence of activated carbon, so that the catalyst is adsorbed on the surface of the activated carbon, which can increase the contact area between the catalyst and the reactants and promote the reaction.

[0026] As a preferred technical solution of the present invention, the solvent is selected from any one of benzene, toluene, ethyl acetate or C6D6 or a combination of at least two thereof, and C6D6 is further preferred.

[0027] It should be noted that C6D6 is the product in which all hydrogen atoms on benzene are replaced by deuterium atoms.

[0028] Preferably, the temperature of the deuteration reaction is 60-200°C, for example, it can be 60°C, 70°C, 80°C, 90°C, 100°C, 110°C, 120°C, 130°C, 140°C, 150°C, 160°C, 170°C, 180°C, 190°C or 200°C, etc.

[0029] Preferably, the deuteration reaction is carried out in a hydrogen atmosphere.

[0030] Preferably, the pressure of the deuteration reaction is 0.01-2 MPa, for example, it can be 0.01 MPa, 0.05 MPa, 0.1 MPa, 0.2 MPa, 0.4 MPa, 0.6 MPa, 0.8 MPa, 1 MPa, 1.2 MPa, 1.4 MPa, 1.6 MPa, 1.8 MPa or 2 MPa.

[0031] Preferably, the deuteration rate of the deuterated mixture is 15% to 99% (for example, it can be 15%, 20%, 28%, 38%, 50%, 53%, 60%, 69%, 70%, 80%, 90% or 99%, etc.), and more preferably 28% to 90%.

[0032] In the present invention, the deuterium substitution rate refers to the percentage of the number of deuterium atoms (D) in the composition or compound to the total number of deuterium atoms and hydrogen atoms (H), that is, deuterium substitution rate = y / (x+y)*100%, wherein y is the number of deuterium atoms in the composition or compound, and x is the number of hydrogen atoms in the composition or compound. Assuming that the composition or compound is all H and there is no D, its deuterium substitution rate is 0%. If all H in the composition or compound is replaced by D, its deuterium substitution rate is 100%.

[0033] It should be noted that the deuteration reaction of the present invention is also carried out in the presence of activated carbon. At the same time, after the deuteration reaction of the present invention is completed, a post-treatment step is also included. The post-treatment method includes cooling, filtering, liquid separation, and drying.

[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. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0035] As a preferred technical solution of the present invention, any one of Ar1 and Ar2 is selected from phenyl, and the other is selected from terphenyl.

[0036] As a preferred technical solution of the present invention, Ar1 and Ar2 are both selected from biphenyl groups.

[0037] As a preferred technical solution of the present invention, the compound A is selected from the following compounds:

[0038]

[0039] Preferably, the compound A is selected from any one of the following compounds:

[0040]

[0041] As a preferred technical solution of the present invention, the Ar 11 is selected from phenyl, said Ar12 ,Ar 13 Any one of them is selected from phenyl, and the other is selected from biphenyl.

[0042] As a preferred technical solution of the present invention, the Ar 11 Selected from biphenyl, Ar 12 ,Ar 13 are selected from phenyl.

[0043] As a preferred technical solution of the present invention, the Ar 12 ,Ar 13 Any one of which is selected from terphenyl.

[0044] As a preferred technical solution of the present invention, the compound of formula III is selected from any one of the following substituted or unsubstituted compounds:

[0045]

[0046]

[0047] The substitution means that the hydrogen atoms in the above compounds can each be independently replaced by a deuterium atom.

[0048] Preferably, the compound of formula III is selected from any one of the following compounds:

[0049]

[0050] As a preferred technical solution of the present invention, the deuterium substitution rate of the first component is 40-88%, for example, it can be 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85% or 88%, etc.

[0051] As a preferred technical solution of the present invention, the deuterium substitution rate of the first component is 55-88%, for example, it can be 55%, 60%, 65%, 70%, 75%, 80%, 85% or 88%.

[0052] As a preferred technical solution of the present invention, taking the volume percentage of the deuterated composition as 100%, the volume percentage of the first component is 30-50%, for example, it can be 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44%, 46%, 48% or 50%, etc.

[0053] As a preferred technical solution of the present invention, taking the volume percentage of the deuterated composition as 100%, the volume percentage of the first component is 40-60%, for example, it can be 40%, 42%, 44%, 46%, 48%, 50%, 52%, 54%, 56%, 58% or 60%, etc.

[0054] As a preferred technical solution of the present invention, taking the volume percentage of the deuterated composition as 100%, the volume percentage of the first component is 50-70%, for example, it can be 50%, 52%, 54%, 56%, 58%, 60%, 62%, 64%, 66%, 68% or 70%, etc.

[0055] It should be noted that the present invention does not impose any particular limitation on the preparation methods of compound A and compound of formula III, and all commonly used preparation methods in the art are applicable.

[0056] 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;

[0057] The organic thin film layer includes a light-emitting layer, and a main material of the light-emitting layer includes the deuterated composition as described in the first aspect.

[0058] Preferably, the light-emitting layer is a phosphorescent light-emitting layer.

[0059] As a preferred technical solution of the present invention, the organic electroluminescent device is a green organic electroluminescent device.

[0060] The luminescent layer in the present invention includes a main material and a doping material of the luminescent layer, wherein the doping material is also called a dye or a phosphorescent luminescent material. The main material of the luminescent layer can be a single compound or a mixture of two or more compounds.

[0061] The light-emitting layer includes a phosphorescent light-emitting layer, and the phosphorescent light-emitting layer includes a green phosphorescent light-emitting layer, a red phosphorescent light-emitting layer, and a blue phosphorescent light-emitting layer.

[0062] The volume percentage of the main material in the phosphorescent layer is 60-99.9% (for example, it can be 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98% or 99.9%, etc.), preferably 70-99.5%, and more preferably 85-95%.

[0063] In the present invention, the doping material of the light-emitting layer may be a phosphorescent material, which is also called a triplet light-emitting material, and refers to the light emitted from a triplet excited state. The specific selection of the phosphorescent material in the present invention is not particularly limited, and the doping materials of the light-emitting layer commonly used in the art are applicable, including but not limited to: a compound having a structure shown in Formula PD:

[0064]

[0065] Wherein, M is selected from any one of Ir, Pt, Pd, Os, Ti, Zr, Hf, Eu, Tb, Tm, Cu or Au;

[0066] Y1-Y4 are each independently selected from carbon or nitrogen;

[0067] Y1 and Y2 can be connected by a single bond or a double bond, and Y3 and Y4 can be connected by a single bond or a double bond;

[0068] Cy1 and Cy2 are each independently selected from phenyl, naphthyl, fluorenyl, spirofluorenyl, indenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothienyl, benzimidazolyl, benzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, N-heterocarbazolyl, N-heterodibenzofuranyl, wherein Cy1 and Cy2 may be optionally linked to each other via a single bond or an organic linking group;

[0069] Any two ligands of M, or more than two ligands, may be connected by a single bond or a double bond, or may be bridged by O or S, or may be connected by any chemical group or chemical structure to form a structural form that conforms to chemical principles;

[0070] R 91 and R 92each independently selected from -H, -D, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid, carboxylate, sulfonic acid, sulfonate, phosphoric acid, phosphate, -SF5, substituted or unsubstituted C1-C60 (e.g., C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkyl, substituted or unsubstituted C2-C6 C2-C60 (for example, C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkynyl, substituted or unsubstituted C1-C60 (for example, C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) C2-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9 or C10) heterocycloalkyl, substituted or unsubstituted C6-C60 (for example, C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) aryl, substituted or unsubstituted C6-C60 (for example, C2, C3, C4, C5, C6, C7, C8, C9 or C10) For example, it can be any one of C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) aryloxy, substituted or unsubstituted C6-C60 (for example, it can be C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) arylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0071] a1 and a2 are each independently an integer selected from 1-5, for example, 1, 2, 3, 4 or 5;

[0072] b is an integer selected from 0-4, for example, 0, 1, 2, 3 or 4;

[0073] a is selected from 1, 2 or 3;

[0074] L1 is a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand.

[0075] Preferably, the compound of formula PD is selected from any one of the following compounds:

[0076]

[0077]

[0078]

[0079]

[0080] In a third aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the second aspect.

[0081] Compared with the prior art, the present invention has the following beneficial effects:

[0082] In the present invention, the specific composition of the deuterated composition is designed, so that the deuterated composition is used as the main material of the light-emitting layer, and the prepared OLED device has a lower driving voltage, a higher current efficiency and a longer lifespan. DETAILED DESCRIPTION

[0083] For the convenience of understanding the present invention, the present invention lists the following embodiments. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0084] Example 1

[0085] This embodiment provides a H-1D series deuterated mixture, and the reaction equation is as follows:

[0086]

[0087] The structure on the right side of the reaction equation indicates that the hydrogen atom at an unspecified position in the raw material H-1 is replaced by a deuterium atom, and the same applies below.

[0088] The preparation method of the above H-1D series deuterated mixture is as follows:

[0089] At room temperature, H-1 (5.6 g, 0.01 mol), palladium chloride (0.0177 g, 0.0001 mol), activated carbon (0.2 g), D2O (20 mL) and C6D6 (200 mL) were added to a 500 mL autoclave, and hydrogen was introduced to a pressure of 0.02 MPa, and then the temperature was raised to 90 ° C for reaction for a certain period of time, and then the temperature was lowered to room temperature, filtered, and separated. The organic layer after separation was dried with magnesium sulfate, decolorized with a short silica gel column, concentrated to dryness, and vacuum dried for 24 hours to obtain a series of H-1D deuterated mixtures;

[0090] After the products prepared at different reaction times were sublimated, the deuteration rate was detected (the deuteration rate was tested by the internal standard method, for example, the test can be carried out according to the method described in the document "Wu Yurong, Chen Minzhu, Determination of the content of deuterated bromobenzene by 1HNMR method [J], Journal of Sichuan University: Natural Science Edition, 1997, 34 (6): 2"). The values ​​of the reaction time and the deuteration rate of the product are shown in Table 1 below:

[0091] Table 1

[0092] Serial number Tritiated mixture Reaction time / (h) Tritium generation rate 1 H-1D01 1 9.81％ 2 H-1D02 20 56.14％ 3 H-1D03 60 88.49％ 4 H-1D04 100 98.26％

[0093] Example 2

[0094] This embodiment provides a H-2D series deuterated mixture, and the reaction equation is as follows:

[0095]

[0096] The preparation method of the above-mentioned H-2D series deuterated mixtures refers to the preparation method of the deuterated mixture provided in Example 1, the only difference is that H-1 is replaced by an equal amount of H-2, and other conditions are the same as in Example 1.

[0097] After the products prepared at different reaction times were sublimated, the deuteration rate was detected (the test method is the same as above). The values ​​of the reaction time and the deuteration rate of the product are shown in Table 2 below:

[0098] Table 2

[0099] Serial number Tritiated mixture Reaction time / (h) Deuterium substitution rate 1 H-2D01 1 9.37％ 2 H-2D02 10 44.71％ 3 H-2D03 20 56.48％ 4 H-2D04 60 85.41％ 5 H-2D05 100 98.82％

[0100] Example 3

[0101] This embodiment provides a H-3D series deuterated mixture, and the reaction equation is as follows:

[0102]

[0103] The preparation method of the above-mentioned H-3D series deuterated mixture refers to the preparation method of the deuterated mixture provided in Example 1, the only difference is that H-1 is replaced by H-3 of the same amount of substance, and other conditions are the same as in Example 1.

[0104] After the products prepared at different reaction times were sublimated, the deuteration rate was detected (the test method is the same as above). The values ​​of the reaction time and the deuteration rate of the product are shown in Table 3 below:

[0105] Table 3

[0106] Serial number Tritiated mixture Reaction time / (h) Tritium generation rate 1 H-3D01 1 9.79％ 2 H-3D02 20 59.98％ 3 H-3D03 60 86.12％ 4 H-3D04 100 99.11％

[0107] Example 4

[0108] This embodiment provides a H-4D series deuterated mixture, and the reaction equation is as follows:

[0109]

[0110] The preparation method of the above H-4D series deuterated mixtures refers to the preparation method of the deuterated mixture provided in Example 1, the only difference is that H-1 is replaced by an equal amount of H-4, and other conditions are the same as in Example 1.

[0111] After the products prepared at different reaction times were sublimated, the deuteration rate was detected (the test method is the same as above). The values ​​of the reaction time and the deuteration rate of the product are shown in Table 4 below:

[0112] Table 4

[0113] Serial number Tritiated mixture Reaction time / (h) Tritium generation rate 1 H-4D01 1 9.59％ 2 H-4D02 20 57.48％ 3 H-4D03 60 86.72％ 4 H-4D04 100 99.21％

[0114] Comparative Example 1

[0115] This comparative example prepares the DH-1D series deuterated mixture, and its reaction equation is as follows:

[0116]

[0117] The preparation method of the above-mentioned DH-1D series deuterated mixture refers to the preparation method of the deuterated mixture provided in Example 1, the only difference is that H-1 is replaced by DH-1 of equal amount, and other conditions are the same as in Example 1.

[0118] After the products prepared at different reaction times were sublimated, the deuteration rate was detected (the test method is the same as above). The values ​​of the reaction time and the deuteration rate of the product are shown in Table 5 below:

[0119] Table 5

[0120] Serial number Tritiated mixture Reaction time / (h) Tritium generation rate 1 DH-1D01 1 9.34％ 2 DH-1D02 20 56.81％ 3 DH-1D03 60 87.72％ 4 DH-1D04 100 99.12％

[0121] Comparative Example 2

[0122] This comparative example prepares a DH-2D series deuterated mixture, and the reaction equation is as follows:

[0123]

[0124] The preparation method of the above DH-2D series deuterated mixtures refers to the preparation method of the deuterated mixture provided in Example 1, the only difference is that H-1 is replaced by DH-2 of equal amount, and other conditions are the same as in Example 1.

[0125] After the products prepared at different reaction times were sublimated, the deuteration rate was detected (the test method is the same as above). The values ​​of the reaction time and the deuteration rate of the product are shown in Table 6 below:

[0126] Table 6

[0127] Serial number Tritiated mixture Reaction time / (h) Tritium generation rate 1 DH-2D01 1 9.65％ 2 DH-2D02 20 56.27％ 3 DH-2D03 60 87.73％ 4 DH-2D04 100 98.34％

[0128] In the process of preparing OLED devices, the first component provided by the present invention needs to be evaporated by evaporation, so it is necessary to ensure that the components of the evaporation remain relatively stable. Therefore, the following evaporation experiments were conducted: 0.5 g of H-1D01 and H-101D03 were respectively put into the crucible of the evaporation machine, and the evaporation temperature was 100 °C. -6 Pa~9×10 -5 Pa pressure, heated to 300 ° C, the material in the crucible was sequentially evaporated onto the glass substrates numbered 1-6 until about 10% of the material in the crucible remained. According to the order of evaporation, a total of 6 glass substrates were obtained. The deuterium substitution rate of the materials on these 6 glass substrates was analyzed separately, as shown in Table 7 below:

[0129] Table 7

[0130]

[0131] It can be seen from the contents of the above table that the deuterium substitution rates of the materials evaporated onto the glass substrate at different time periods are basically the same.

[0132] The specific structures of some compositions used in the following device embodiments and device comparative examples are as follows:

[0133]

[0134] Device Example 1

[0135] This device embodiment provides an organic electroluminescent device, and the composition provided by the present invention is selected as a green light host material in the organic electroluminescent device;

[0136] The structure of the organic electroluminescent device is: ITO / HT-1 (40nm) / green light host material (35nm): PGD-1 [10%] / ETL-1 (25nm) / LiF (0.5nm) / Al (150nm).

[0137] The preparation process of organic electroluminescent device is as follows:

[0138] The preparation method of the green organic electroluminescent device is as follows:

[0139] The material was placed in a vacuum chamber and evacuated to 1×10 -5 ~1×10 -6 Pa was vacuum evaporated onto the cleaned ITO substrate in turn to prepare an OLED device.

[0140] PGD-1[10%] refers to the doping ratio of the dye, that is, the volume ratio of the main material to the dye PGD-1 is 90:10; HT-1 is a hole transport material, and ETL-1 is an electron transport material.

[0141] The green light main body material of the green light organic electroluminescent device provided in the present device embodiment includes a first component and a second component, the first component is H-2D01, and the second component is compound E-2. The first component and the second component are placed in different evaporation sources for heating, and the heating speed is controlled so that the volume ratio of each component evaporated on the substrate is 1:1, as the green light main material.

[0142] Device Examples 2-11

[0143] Device Comparative Example 2-11 provides an organic electroluminescent device, which is different from Device Example 1 only in that the green light host material is different (see Table 8 below for details), and the other preparation steps and conditions are the same as those of Device Example 1.

[0144] Device Comparison Examples 1-5

[0145] Device Comparative Examples 1-5 each provide an organic electroluminescent device, which differs from Device Example 1 only in that the green light host material is different (see Table 8 below for details), and the other preparation steps and conditions are the same as those of Device Example 1.

[0146] Performance Test:

[0147] The test measured the brightness, driving voltage, current efficiency, and life test LT90 of the prepared organic electroluminescent device. Among them, the life test LT90 refers to the current density at room temperature (25-27°C) at the initial brightness (here 1000cd / m 2 The time required for the brightness to decrease to 90% of the initial brightness is measured.

[0148] The test results are detailed in Table 8 below.

[0149] Table 8

[0150]

[0151] From the above content, it can be seen that in the present invention, by designing the specific composition of the deuterated composition, the deuterated composition is used as the main material of the light-emitting layer, and the OLED device prepared has a lower driving voltage, a higher current efficiency and a longer life.

[0152] It can be seen from device examples 1 to 5 that as the deuterium substitution rate of the first component increases, the driving voltage of the prepared OLED device first decreases and then increases. Therefore, the deuterium substitution rate of the first component is preferably 40-88%.

[0153] It should be noted that the deuterium substitution rate of the first component of device embodiment 2 is 44.71%, and the deuterium substitution rate of the first component of device embodiment 4 is 85.41%. According to the common sense in the art and the specific data of the embodiments of the present invention, even if the same reaction conditions and the same reaction time are used, there will be some differences in the deuterium substitution rate. Therefore, it is preferred that the deuterium substitution rate of the first component is 40-88%, which is more reasonable than selecting 44.71-85.41%.

[0154] The driving voltage of the OLED device provided in device embodiment 5 is 5.07V, which is not much different from the driving voltages of the OLED devices provided in device embodiments 2 and 3. However, considering the increase in the deuterium substitution rate, the cost increases. Therefore, in order to obtain a low-voltage device, the deuterium substitution rate of the first component is preferably 40-88%.

[0155] It can be seen from device examples 1 to 5 that as the deuterium substitution rate of the first component increases, the current efficiency of the prepared OLED device first increases and then decreases. The current efficiency of the OLED devices provided by device examples 3 and 4 is better. Therefore, the deuterium substitution rate of the first component is preferably 55-88%.

[0156] It should be noted that the deuterium substitution rate of the first component in device embodiment 3 is 56.48%, and the deuterium substitution rate of the first component in device embodiment 4 is 85.41%. According to the common sense in the art and the specific data of the embodiments of the present invention, even if the same reaction conditions and the same reaction time are used, there will be some differences in the deuterium substitution rate. Therefore, it is preferred that the deuterium substitution rate of the first component is 55-88%, which is more reasonable than selecting 56.48-85.41%.

[0157] It can be seen from Device Examples 1 to 5 that as the deuteration rate of the first component increases, the LT90 lifetime of the prepared OLED devices first increases and then decreases. The LT90 lifetime of the OLED devices provided by Device Examples 2 to 4 is relatively high. Therefore, the deuteration rate of the first component is preferably between 40 and 88%.

[0158] It should be noted that the deuterium substitution rate of the first component in device embodiment 2 is 44.71%, and the deuterium substitution rate of the first component in device embodiment 4 is 85.41%. According to the common sense in the art and the specific data of the embodiments of the present invention, even if the same reaction conditions and the same reaction time are used, there will be some differences in the deuterium substitution rate. Therefore, it is preferred that the deuterium substitution rate of the first component is 40-88%, which is more reasonable than selecting 44.71-85.41%.

[0159] It can be seen from device embodiment 3 and device embodiment 6 that the deuterium substitution rates of the first components of the two are similar, and the driving voltage of the OLED device provided by device embodiment 6 is lower.

[0160] It can be seen from device embodiment 3 and device embodiment 7 that the deuterium substitution rates of the first components of the two are similar, and the current efficiency of the OLED device provided by device embodiment 7 is higher.

[0161] It can be seen from device embodiment 3 and device embodiment 8 that the deuteration rates of the first components of the two are similar, and the OLED device provided by device embodiment 6 has a better LT90 lifespan.

[0162] Device Examples 12-16

[0163] The structure of the organic electroluminescent device provided in device examples 12-16 is: ITO / HT-1 (40nm) / green light host material (35nm): PGD-2 [10%] / ETL-1 (25nm) / LiF (0.5nm) / Al (150nm).

[0164] The preparation process of organic electroluminescent device is as follows:

[0165] The preparation method of the green organic electroluminescent device is as follows:

[0166] The material was placed in a vacuum chamber and evacuated to 1×10 -5 ~1×10 -6 Pa was vacuum evaporated onto the cleaned ITO substrate in turn to prepare an OLED device.

[0167] PGD-2[10%] refers to the doping ratio of the dye, that is, the volume ratio of the main material to the dye PGD-2 is 90:10; HT-1 is a hole transport material, and ETL-1 is an electron transport material.

[0168] The green light main material of the green light organic electroluminescent device includes a first component and a second component, the first component is H-2D03, and the second component is compound E-2. The first component and the second component are placed in different evaporation sources for heating, and the heating speed is controlled so that the volume ratio of each component evaporated onto the substrate is different (see Table 9 below for specific ratios), as the green light main material.

[0169] The performance of the organic electroluminescent devices provided in device embodiments 12-16 was tested using the same testing methods as above. The test results are detailed in Table 9 below.

[0170] Table 9

[0171]

[0172] From the above content, it can be seen from device embodiments 12 to device embodiments 16 that when the volume proportion of the first component in the green light main material is 30-50%, the driving voltage of the prepared OLED device is lower, and when the volume proportion of the first component is 30-40%, the driving voltage of the prepared OLED device is even lower.

[0173] When the volume proportion of the first component in the green light host material is 40-60%, the current efficiency of the prepared OLED device is better.

[0174] When the volume proportion of the first component in the green light host material is 50-70%, the LT90 life of the prepared OLED device is better.

[0175] In summary, the present invention designs the specific composition of the deuterated composition, and thus uses the deuterated composition as the main material of the light-emitting layer to prepare an OLED device with lower driving voltage, higher current efficiency and longer life.

[0176] The applicant declares that the present invention illustrates the detailed process flow of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned detailed process flow, that is, it does not mean that the present invention must rely on the above-mentioned detailed process flow to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A deuterated composition, characterized in that: The deuterated composition includes a first component and a second component; The first component includes a deuterated mixture obtained by deuterating compound A, wherein compound A has the following structure: Wherein, Ar1 and Ar2 are each independently selected from any one of phenyl, biphenyl or terphenyl; The second component comprises a compound of formula III: Among them, Ar 11 ,Ar 12 ,Ar 13 Each independently selected from any one of phenyl, biphenyl or terphenyl; The hydrogen atoms in the compound of formula III may each independently be replaced by a deuterium atom.

2. The deuterated composition according to claim 1, characterized in that Any one of Ar1 and Ar2 is selected from phenyl, and the other is selected from terphenyl; And / or, Ar1 and Ar2 are both selected from biphenyl groups.

3. The deuterated composition according to claim 1, characterized in that The compound A is selected from the following compounds:

4. The deuterated composition according to claim 1, characterized in that The Ar 11 is selected from phenyl, said Ar 12 ,Ar 13 Any one of them is selected from phenyl, and the other is selected from biphenyl; and / or, the Ar 11 Selected from biphenyl, Ar 12 ,Ar 13 are all selected from phenyl; and / or, the Ar 12 ,Ar 13 Any one of which is selected from terphenyl.

5. The deuterated composition according to claim 1, characterized in that The compound of formula III is selected from any one of the following substituted or unsubstituted compounds: The substitution means that the hydrogen atoms in the above compounds can each be independently replaced by a deuterium atom.

6. The deuterated composition according to claim 1, characterized in that The deuterium substitution rate of the first component is 40-88%.

7. The deuterated composition according to claim 1, characterized in that Taking the volume percentage of the deuterated composition as 100%, the volume percentage of the first component is 30-50%.

8. The deuterated composition according to claim 1, characterized in that Taking the volume percentage of the deuterated composition as 100%, the volume percentage of the first component is 40-60%.

9. The deuterated composition according to claim 1, characterized in that Taking the volume percentage of the deuterated composition as 100%, the volume percentage of the first component is 50-70%.

10. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode, a cathode and an organic thin film layer arranged between the anode and the cathode; The organic thin film layer comprises a light-emitting layer, and a main material of the light-emitting layer comprises the deuterated composition according to any one of claims 1 to 9.

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