Composition and organic electroluminescent device

Abstract

The invention provides a composition and an organic electroluminescent device, and relates to the technical field of organic electroluminescent materials. According to the invention, the specific composition is used as the material of the light-emitting layer of the OLED light-emitting device, so that the OLED light-emitting device has lower driving voltage, higher current efficiency and longer service life.

Description

Technical Field

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

[0002] Compared to other flat panel displays, such as liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs), organic light-emitting devices (OLEDs) have superior viewing angle characteristics, higher brightness, faster response speed, and lower driving voltage. Moreover, they have a simpler structure and are easier to process, so they have been fully developed and can be used as light sources for flat panel displays (such as wall-mounted TVs) or as backlight units for displays, lighting fixtures, advertising boards, etc.

[0003] The structure of an organic light-emitting diode (OLED) device consists of an anode, a cathode, and an organic layer between them. To improve the efficiency and stability of OLEDs, the organic layer comprises multiple functional layers made of different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer, an emissive layer, an electron transport layer (ETL), and an electron injection layer (EIL). Currently, organic light emission has become a mainstream display technology, and correspondingly, various novel OLED materials have been developed.

[0004] To meet the higher demands of people for OLED devices, there is an urgent need in the field to develop more types of materials to improve the performance of OLED devices in terms of current efficiency, lifetime, and other aspects. Summary of the Invention

[0005] In view of the shortcomings of the prior art, the purpose of this invention is to provide a composition and an organic electroluminescent device.

[0006] To achieve this objective, the present invention adopts the following technical solution:

[0007] In a first aspect, the present invention provides a composition comprising at least a first compound and a second compound, wherein the first compound is selected from compounds represented by Formula A, the second compound is selected from compounds represented by Formula I, and the first compound is different from the second compound;

[0008]

[0009] Formula A;

[0010] In Formula A, Ar1 and Ar2 are each independently selected from at least one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted biphenyl, wherein each of the substituted substituents is independently a deuterium atom.

[0011] In the compound shown in Formula A, each hydrogen atom can be independently replaced by a deuterium atom;

[0012]

[0013] Formula I

[0014] In Formula I, the Ar 11 Ar 12 Each is independently selected from any one of substituted or unsubstituted C6~C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, C40) aryl groups and substituted or unsubstituted C12~C40 (e.g., C12, C16, C20, C24, C28, C30, C32, C36, C40) heteroaryl groups;

[0015] The R 11 R 12 Each is independently selected from any one of the following: substituted or unsubstituted C1-C6 straight-chain or branched alkyl groups (e.g., methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, hexyl); substituted or unsubstituted C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, C40) aryl groups; and substituted or unsubstituted C12-C40 (e.g., C12, C16, C20, C24, C28, C30, C32, C36, C40) heteroaryl groups.

[0016] Ar 11 Ar 12 R 11 R 12 In this embodiment, each of the substituents is independently selected from at least one of the following: a deuterium atom, a C1-C6 straight-chain or branched alkyl group (e.g., methyl, ethyl, propyl, n-butyl, tert-butyl, n-pentyl, isopentyl, hexyl), a C6-C20 (e.g., C6, C8, C10, C12, C16, C20) aryl group, and a C6-C20 (e.g., C6, C8, C10, C12, C16, C20) heteroaryl group;

[0017] The m and n are each independently selected from integers from 0 to 4, for example, they can be 0, 1, 2, 3 or 4;

[0018] In the compound shown in Formula I, each hydrogen atom can be independently replaced by a deuterium atom.

[0019] In this invention, by designing the structures of compounds of formula A and formula I in the composition, the composition is used as the light-emitting layer material of OLED light-emitting devices, so that the OLED light-emitting devices have lower driving voltage, higher current efficiency and longer lifespan.

[0020] In this invention, "D" represents a deuterium atom. Unless otherwise specified, "H" and "hydrogen" both represent "protium".

[0021] Preferably, the Ar 11 Ar 12 R 11 R 12 In this aryl group, C6 to C40 are selected from any one of phenyl, biphenyl, naphthyl, phenanthryl, anthracene, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, triphenylene, fluoranyl, pyrene, perylene, spirofluorenyl, indo[a]fluorenyl, or hydrogenated benzo[a]anthryl.

[0022] Preferably, the Ar 11 Ar 12 R 11 R 12 In this context, the C12~C40 heteroaryl groups are selected from any one of dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, and benzonaphthothiophenyl.

[0023] Preferably, Ar 11 Ar 12 R 11 R 12 In the case where the substituent is a C6-C20 aryl group, the C6-C20 aryl group is preferably phenyl, naphthyl, or biphenyl.

[0024] Preferably, Ar 11 Ar 12 R 11 R 12 In the case where the substituent is a C6-C20 heteroaryl, the C6-C20 heteroaryl is preferably dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, or naphthobenzothiophenyl.

[0025] Preferably, the Ar 11 Selected from , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , Any one of them.

[0026] Preferably, the Ar 12 Selected from , , , , , , , , , , , , , , , , Any one of them.

[0027] Preferably, R11 and R12 are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, ... , Any one of them.

[0028] Preferably, the compound represented by Formula I is selected from any one of the following substituted or unsubstituted compounds:

[0029]

[0030]

[0031] ;

[0032] The substitution refers to the fact that each hydrogen atom in the above compound can be independently replaced by a deuterium atom.

[0033] Preferably, the compound represented by formula A is selected from any one of the following compounds, whether substituted or unsubstituted:

[0034] ;

[0035] The substitution refers to the fact that each hydrogen atom in the above compound can be independently replaced by a deuterium atom.

[0036] Preferably, the compound represented by Formula I is selected from any one of the following compounds:

[0037] , , , , , , , , , , , , , , .

[0038] Preferably, the compound represented by formula A is selected from any one of the following compounds:

[0039] , , , , , , , , , , .

[0040] Preferably, the first compound is selected from the compound shown in Formula A, the second compound is selected from the compound shown in Formula I-1, and the first compound is different from the second compound;

[0041]

[0042] Formula I-1;

[0043] In Equation I-1, Ar 111 for Ar 61 It is selected from at least one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted biphenyl, wherein each of the substituted substituents is independently a deuterium atom;

[0044] Ar 121It is selected from at least one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted biphenyl, wherein each of the substituted substituents is independently a deuterium atom;

[0045] In the compound shown in Formula I-1, each hydrogen atom can be independently replaced by a deuterium atom.

[0046] Preferably, in the composition, the proportions of the first compound and the second compound are different or the same; the proportions represent mass ratios or volume ratios.

[0047] The proportion here has two meanings:

[0048] One meaning is the mass ratio. When the first compound and the second compound are mixed and used as a premixed material, since both materials are solids, generally existing in powder form, measuring volume is not practical, but mass is easier to measure. In this case, the ratio of the first compound and the second compound refers to their mass ratio.

[0049] Another meaning refers to volume ratio. When fabricating OLED devices, different materials are placed in different evaporation sources, and the evaporation rate of different materials is controlled so that a mixture of a specified ratio is used as the light-emitting layer material in the organic electroluminescent device. The different or the same evaporation rates can be regarded as the different or the same volume ratio of the materials evaporated onto the substrate.

[0050] The proportions of the first compound and the second compound in the sense of this invention are different or the same, including the above-mentioned different and the same mass and / or volume proportions.

[0051] Preferably, with the sum of the volume percentages of the first compound and the second compound being 100%, the volume percentage of the first compound is 0.1% to 49% (for example, it can be 0.1%, 1%, 5%, 10%, 12%, 15%, 18%, 20%, 25%, 30%, 35%, 40%, 45%, or 49%), more preferably 10% to 40%, further preferably 10% to 30%, even more preferably 10% to 20%, and still more preferably 15% to 20%.

[0052] Preferably, with the sum of the volume percentages of the first compound and the second compound being 100%, the volume percentage of the first compound is 51% to 95% (for example, it can be 51%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 92%, or 95%), more preferably 60% to 95%, further preferably 70% to 95%, even more preferably 80% to 95%, and still more preferably 90% to 95%.

[0053] Preferably, the volume percentage of the first compound is 70% to 90%, more preferably 75% to 85%, based on the sum of the volume percentages of the first compound and the second compound being 100%.

[0054] Preferably, with the sum of the mass percentages of the first compound and the second compound being 100%, the mass percentage of the first compound is 0.1% to 49% (for example, it can be 0.1%, 1%, 5%, 10%, 12%, 15%, 18%, 20%, 25%, 30%, 35%, 40%, 45%, or 49%), more preferably 10% to 40%, further preferably 10% to 30%, even more preferably 10% to 20%, and still more preferably 15% to 20%.

[0055] Preferably, with the sum of the mass percentages of the first compound and the second compound being 100%, the mass percentage of the first compound is 51% to 95% (for example, it can be 51%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 92%, or 95%), more preferably 60% to 95%, further preferably 70% to 95%, even more preferably 80% to 95%, and still more preferably 90% to 95%.

[0056] Preferably, the mass percentage of the first compound is 70% to 90%, more preferably 75% to 85%, based on the sum of the mass percentages of the first compound and the second compound being 100%.

[0057] Preferably, the first compound and the second compound are in the same proportion, the proportion being a mass ratio or a volume ratio, that is, the volume percentage of the first compound is 50% when the sum of the volume percentages of the first compound and the second compound is 100%; or the mass percentage of the first compound is 50% when the sum of the mass percentages of the first compound and the second compound is 100%.

[0058] In this invention, the amount of compound I and compound A in the composition is designed to enable OLED light-emitting devices to have lower driving voltage, higher current efficiency and longer lifespan.

[0059] 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 organic thin film layer comprising the composition described in the first aspect.

[0060] Preferably, the organic thin film layer includes a light-emitting layer, and the light-emitting layer includes the composition described above.

[0061] Preferably, the light-emitting layer further includes a doping material, the doping material comprising a compound having the structure shown in Formula II:

[0062]

[0063] Formula II;

[0064] In formula II, R 21 R 22 and R 23 Each is independently selected from hydrogen, C1-C12 (e.g., C1, C2, C4, C6, C8, C10, or C12) straight-chain or branched alkyl groups, C6-C12 (e.g., C6, C7, C8, C9, C10, C11, or C12) cycloalkyl groups, -NAr 23 Ar 24 Any one of them;

[0065] Ar 21 Ar 22 Ar 23 Ar 24 Each is independently selected from any one of substituted or unsubstituted C6~C20 (e.g., C6, C8, C10, C12, C14, C16, C18 or C20) aryl, substituted or unsubstituted C3~C20 (e.g., C3, C6, C8, C10, C12, C14, C16, C18 or C20) heteroaryl;

[0066] Ar 21 Ar 22 Ar 23 Ar 24 In this context, each of the substituents is independently selected from C1-C5 straight-chain or branched alkyl groups (e.g., methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl) or C6-C12 aryl groups (e.g., phenyl, biphenyl, naphthyl).

[0067] Preferably, the Ar 21 Ar 22 Ar 23 Ar 24 Each independently selected , , , , , , , , , , , , , , , , Any of the following, with dashed lines representing connection points.

[0068] Preferably, R 21 R 22 and R 23 Each is independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, or adamantyl.

[0069] Preferably, the compound of formula II is selected from any one of the following compounds:

[0070] .

[0071] Preferably, the light-emitting layer further includes a doping material, the doping material comprising a compound having the structure shown in Formula III:

[0072]

[0073] Formula III;

[0074] In Formula III, Ar 31 Ar 32 Ar 33 and Ar 34 Each is independently selected from any one of substituted or unsubstituted C6~C22 (e.g., C6, C8, C10, C12, C14, C16, C18 or C20) aryl, substituted or unsubstituted C12~C40 (e.g., C12, C16, C20, C24, C28, C30, C32, C36 or C40) heteroaryl;

[0075] R 31 Selected from any one of phenyl, naphthyl, or biphenyl;

[0076] a is selected from 0 or 1;

[0077] Ar 31 Ar 32 Ar 33 Ar 34 In this context, each of the substituents is independently selected from C1-C5 straight-chain or branched alkyl groups (e.g., methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl) or C6-C12 aryl groups (e.g., phenyl).

[0078] Preferably, the Ar 31 Ar32 Ar 33 and Ar 34 Each independently selected , , , , , , , , , Any one or at least two of the above, with dashed lines indicating connection sites.

[0079] Preferably, the compound of formula III is selected from any one of the following compounds:

[0080] .

[0081] Preferably, the light-emitting layer further includes a doping material, the doping material comprising a compound having the structure shown in Formula IV:

[0082]

[0083] Formula IV;

[0084] In Formula IV, X1, X2, X3, and X4 are each independently selected from O, S, and CR. 81 R 82 NR 83 ;

[0085] R 81 R 82 Each is independently selected from C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, or C10) alkyl or C6-C15 (e.g., C6, C7, C10, C12, or C15) aryl, R 81 and R 82 They can be connected in a ring using a single key;

[0086] R 83 Selected from C1 to C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, or C10) alkyl or C6 to C15 (e.g., C6, C7, C10, C12, or C15) aryl;

[0087] R 61 ~R 76Each is independently selected from H, D, F, CN, C1~C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, or C10) alkyl, C1~C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, or C10) alkoxy, C6~C15 (e.g., C6, C7, C10, C12, or C15) aryl, NR 85 R 86 Any one of them;

[0088] R 85 R 86 Each is independently selected from C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, or C10) alkyl or C6-C15 (e.g., C6, C7, C10, C12, or C15, etc.) aryl, and R 85 R 86 They can be connected in a ring using a single key;

[0089] The R 61 ~R 76 When each alkyl group is independently selected from C1 to C10 (e.g., it can be C1, C2, C3, C4, C5, C6, C7, C8, C9, or C10), any two adjacent R groups 61 ~R 76 They can be directly connected to form a ring;

[0090] The R 61 ~R 76 When each aryl group is independently selected from C6~C15 (e.g., it can be C6, C7, C10, C12, or C15), R 61 ~R 76 Can be used with R 61 ~R 76 The benzene rings they belong to are connected by -O-, -S-, and -CR-. 87 R 88 -、-NR 89 -Bridge, R 87 R 88 R 89 Each is independently selected from C1 to C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, or C10) alkyl or C6 to C15 (e.g., C6, C7, C10, C12, or C15) aryl.

[0091] Preferably, the C1-C10 alkyl group is selected from any one of methyl, ethyl, propyl, butyl, pentyl, hexyl, and adamantyl, and more preferably from any one of methyl, ethyl, isopropyl, tert-butyl, and adamantyl.

[0092] Preferably, the C1-C10 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, and adamantoxy.

[0093] Preferably, the C6-C15 aryl group is selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, phenanthryl, and anthracene.

[0094] Examples are given below:

[0095] R 62 Selected from NR 85 R 86 And R 85 R 86 When all are selected from ethyl groups, the compounds of formula IV can be as follows:

[0096] .

[0097] R 62 Selected from NR 85 R 86 And R 85 R 86 All are selected from ethyl groups, and R 85 R 86 The compounds of formula IV are cyclically linked by single bonds, and their structures are as follows:

[0098] .

[0099] R 62 Selected from NR 85 R 86 And R 85 R 86 When all are selected from phenyl groups, the structure of compound IV is as follows:

[0100] .

[0101] R 62 Selected from NR 85 R 86 And R 85 R 86 All are selected from phenyl, and R 85 R 86 The compounds of formula IV are cyclically linked by single bonds, and their structures are as follows:

[0102] .

[0103] The R 61 ~R 76 When each alkyl group is independently selected from C1 to C10, any two adjacent R groups 61 ~R 76They can be directly connected to form a ring; the R 61 ~R 76 When each aryl group is independently selected from C6 to C15, R 61 ~R 76 Can be used with R 61 ~R 76 The benzene rings they belong to are connected by -O-, -S-, and -CR-. 87 R 88 -、-NR 89 -Bridge, R 87 R 88 R 89 Each is independently selected from C1-C10 alkyl groups or C6-C15 aryl groups;

[0104] Examples are given below:

[0105] R 61 R 62 When all are selected from ethyl groups, the structure of compound IV is as follows:

[0106] .

[0107] R 61 R 62 All are selected from ethyl groups, and R 61 R 62 Directly linked into rings, the structure of compound IV can be as follows:

[0108] .

[0109] R 61 R 62 When all components are selected from phenyl groups, the structure of compound IV is as follows:

[0110] .

[0111] R 61 Selected from phenyl, R 62 Selected from H, the structure of compound IV is as follows:

[0112] .

[0113] R 61 It is a phenyl group, R 61 and R 61 The benzene ring can be connected via -O-, -S-, or -CR. 87 R 88 -、-NR 89 -Bridging, the structure of compound IV is as follows:

[0114]

[0115] .

[0116] Preferably, the compound of formula IV is selected from any one of the following compounds:

[0117] .

[0118] It should be noted that no special restrictions are placed on the preparation methods of compounds of formula I to IV and compound A in this invention, and commonly used preparation methods in the art are applicable.

[0119] Preferably, when the light-emitting layer includes a doped material, the volume percentage or mass percentage of the composition in the light-emitting layer is 60% to 99.9% (e.g., 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98%, 99.9%), and the volume percentage or mass percentage of the doped material is 0.1% to 40% (e.g., 0.1%, 2%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%).

[0120] Preferably, the organic thin film layer further includes at least one of a hole layer and an electron layer.

[0121] In this invention, the hole layer includes one or more of a hole injection layer, a hole transport layer, and an electron blocking layer. This invention does not impose any special restrictions on the specific material selection for the hole layer (including the hole injection layer, hole transport layer, and electron blocking layer); commonly used hole layer materials in the art are applicable.

[0122] In this invention, the electronic layer includes one or more of an electron injection layer, an electron transport layer, and a hole blocking layer. This invention does not impose any special restrictions on the specific selection of materials for the electronic layer (including the electron injection layer, electron transport layer, and hole blocking layer); commonly used electronic layer materials in the art are applicable.

[0123] Thirdly, the present invention provides a display device comprising the organic electroluminescent device as described in the second aspect.

[0124] Compared with the prior art, the present invention has the following beneficial effects:

[0125] In this invention, the structure of compounds of formula A and formula I in the composition is designed, and this composition is used as the light-emitting layer material of OLED light-emitting device, so that the OLED light-emitting device has a lower driving voltage, higher current efficiency and longer life. Detailed Implementation

[0126] 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.

[0127] Preparation Example 1: Synthesis of Intermediate P1-1

[0128]

[0129] Under nitrogen atmosphere, 60 mL of toluene, 40 mL of ethanol, and 15 mL of water were added to a three-necked flask. Then, 3.5 g of 9-(1-naphthyl)-10-boric acid, 3.6 g of 1-bromo-3-iodo-dibenzo[b,d]furan, 2.12 g of sodium carbonate, and 0.23 g of tetraphenylphosphine palladium were added. The mixture was slowly heated to reflux and reacted for 6 hours. After cooling to room temperature, water was added to dissolve the mixture. The organic layer was washed with water and dried with magnesium sulfate. After removing the desiccant, the mixture was concentrated to dryness and crystallized with toluene to obtain intermediate P1-1 (4.1 g).

[0130] The obtained intermediate P1-1 was subjected to mass spectrometry analysis, and the mass-to-charge ratio (m / z) was measured to be 548.08.

[0131] Preparation Example 2: Synthesis of Intermediate P1-D1-1

[0132]

[0133] Following the synthesis of intermediate P1-1, intermediate P1-D1-1 was prepared.

[0134] The obtained intermediate P1-D1-1 was subjected to mass spectrometry analysis, and the mass-to-charge ratio (m / z) was measured to be 556.13.

[0135] Preparation Example 3: Synthesis of Intermediate P4-1

[0136]

[0137] Following the synthesis of intermediate P1-1, intermediate P4-1 was prepared.

[0138] The obtained intermediate P4-1 was subjected to mass spectrometry analysis, and the mass-to-charge ratio (m / z) was measured to be 498.06.

[0139] Preparation Example 4: Synthesis of Intermediate P5-1

[0140]

[0141] Following the synthesis of intermediate P1-1, intermediate P5-1 was prepared.

[0142] The obtained intermediate P5-1 was subjected to mass spectrometry analysis, and the mass-to-charge ratio (m / z) was measured to be 506.11.

[0143] Preparation Example 5: Synthesis of Intermediate P7-1

[0144]

[0145] Following the synthesis of intermediate P1-1, intermediate P7-1 was prepared.

[0146] The obtained intermediate P7-1 was subjected to mass spectrometry analysis, and the mass-to-charge ratio (m / z) was measured to be 548.08.

[0147] Preparation Example 6: Synthesis of Intermediate P8-1

[0148]

[0149] Following the synthesis of intermediate P1-1, intermediate P8-1 was prepared.

[0150] The obtained intermediate P8-1 was analyzed by mass spectrometry, and the mass-to-charge ratio (m / z) was found to be 574.09.

[0151] Preparation Example 7: Synthesis of Intermediate P9-1

[0152]

[0153] Following the synthesis of intermediate P1-1, intermediate P9-1 was prepared.

[0154] The obtained intermediate P9-1 was analyzed by mass spectrometry, and the mass-to-charge ratio (m / z) was found to be 574.09.

[0155] Synthesis Example 1: Synthesis of Compound P1

[0156] This synthetic example provides compound P1 and its synthetic method, which is as follows:

[0157]

[0158] Compound P1 was prepared by referring to the synthesis of intermediate P1-1.

[0159] The obtained compound P1 was analyzed by mass spectrometry, and the mass-to-charge ratio (m / z) was found to be 546.20.

[0160] Synthesis Examples 2-8

[0161] Following the synthesis of compound P1, the following compounds were synthesized using brominated derivatives and borate compounds, and their mass spectra were measured and the m / z values ​​were recorded. See Table 1 below for details.

[0162] Table 1

[0163]

[0164]

[0165] For other compounds whose synthesis methods are not listed, the above methods can be used as a reference for synthesis.

[0166] The specific structures of some of the compounds used in the following device embodiments and device comparative examples are shown below:

[0167] , , , , , , , , , , , , , , , , , , , , , , .

[0168] Device Example 1

[0169] This embodiment of the device provides an organic electroluminescent device, the structure of which is ITO / HT (40nm) / light-emitting layer (30nm) / TPBI (30nm) / LiF (0.5nm) / Al (150nm);

[0170] The fabrication method of the above-mentioned organic electroluminescent device is as follows:

[0171] (1) The glass substrate coated with ITO transparent conductive layer (as anode) is ultrasonically treated in cleaning agent, then rinsed in deionized water, then ultrasonically degreased in a mixed solvent of acetone and ethanol, then dried completely in a clean environment, then cleaned with ultraviolet light and ozone, and bombarded with low-energy cation beam to improve the properties of ITO surface and enhance its bonding ability with hole injection layer.

[0172] (2) Place the glass substrate in a vacuum chamber and evacuate it to 1×10⁻⁶. -6 ~1×10 -5Pa, HT is vacuum-deposited on the anode as a hole transport layer at a deposition rate of 0.01 nm / s and a film thickness of 40 nm.

[0173] (3) A light-emitting layer is vacuum-deposited on the hole transport layer at a deposition rate of 0.01 nm / s and a deposition film thickness of 30 nm. The light-emitting layer is composed of a host material and a dopant material. The host material is composed of compounds P1 and BH1 (the volume ratio of compounds P1 and BH1 is 5:5), and the dopant material is BD-2. The volume ratio of the host material to the dopant material is 97:3. When the host material of the light-emitting layer is two or more substances, different host materials are placed in different evaporation sources, and the deposition rate of different host materials is controlled so that the mixture with a specified volume ratio is used as the host material of the light-emitting layer in the organic electroluminescent device.

[0174] (4) TPBI is vacuum-deposited on the organic light-emitting layer as the electron transport layer of the organic electroluminescent device; the deposition rate is 0.01 nm / s and the deposition film thickness is 30 nm.

[0175] (5) Vacuum evaporation of 0.5 nm LiF and 150 nm Al on the electron transport layer as electron injection layer and cathode to obtain the organic electroluminescent device.

[0176] Device Examples 2-5

[0177] Device Examples 2-5 each provide an organic electroluminescent device, which differs from Device Example 1 only in that the main material of the light-emitting layer is different. The specific composition of the main material of the light-emitting layer is detailed in Table 2 below. Furthermore, when the main material of the light-emitting layer is composed of multiple compounds, the volume ratio between the compounds of each main material is the same; other structures, materials and preparation methods are the same as those in Device Example 1.

[0178] Device Comparison Examples 1-4

[0179] Comparative Examples 1 to 4 each provide an organic electroluminescent device, which differs from Device Example 1 only in that the main material of the light-emitting layer is different, and when the main material of the light-emitting layer is composed of multiple compounds, the volume ratio between the compounds of each main material is the same; the specific composition of the main material of the light-emitting layer is detailed in Table 2 below, and the other structures, materials and preparation methods are the same as those of Device Example 1.

[0180] Performance testing:

[0181] The driving voltage, current efficiency, and lifetime LT90 of the organic electroluminescent devices provided above were tested. LT90 refers to the time required for the brightness to drop to 90% of the original brightness while maintaining the current density at an initial brightness of 1000 nits. The specific test results are shown in Table 2. The driving voltage, current efficiency, and LT90 are all relative values ​​(based on device example 1).

[0182] Table 2

[0183]

[0184] Note: In the table above, " / " indicates that the main material of the light-emitting layer in the embodiment or comparative example of the device does not contain the compound.

[0185] In the composition of Device Example 1, the first compound is compound P1, in which the two meta positions of the O of dibenzofuran are connected to the anthracene ring and the benzene ring, respectively. In Device Comparative Example 1, the first compound is compound D1, in which the para and ortho positions of the O of dibenzofuran are connected to the anthracene ring and the benzene ring, respectively. The specific connection mode of compound P1 makes it better for the material to form films when used in combination with the second compound, and the energy level matching of the second compound is more reasonable. The voltage, efficiency and lifetime of the prepared device are improved.

[0186] In the composition of Device Example 1, the first compound is compound P1, in which the two meta positions of O in dibenzofuran are connected to the anthracene ring and the benzene ring, respectively. In Device Comparative Example 2, the first compound is compound D2. The specific connection mode of compound P1 makes it better for the material to form films when used in combination with the second compound, and the energy level matching of the second compound is more reasonable. The voltage, efficiency and lifetime of the prepared device are improved.

[0187] Comparing device examples 1-4 with device example 5, it can be seen that when the second compound conforms to formula I-1, the device voltage and efficiency are significantly improved.

[0188] Device Examples 6-9

[0189] Device Examples 6-9 each provide an organic electroluminescent device, which differs from Device Example 1 only in that the main material of the light-emitting layer is different. The specific composition of the main material of the light-emitting layer is detailed in Table 3 below. Furthermore, when the main material of the light-emitting layer is composed of multiple compounds, the volume ratio between the compounds of each main material is the same. In addition, BD-2 is replaced with BD-1. Other structures, materials and preparation methods are the same as those in Device Example 1.

[0190] Performance testing:

[0191] The driving voltage, current efficiency, and lifetime LT90 of the organic electroluminescent devices provided above were tested. LT90 refers to the time required for the brightness to drop to 90% of the original brightness while maintaining the current density at an initial brightness of 1000 nits. The specific test results are shown in Table 3. The driving voltage, current efficiency, and LT90 are all relative values ​​(based on device example 6).

[0192] Table 3

[0193]

[0194] Device Examples 10-11

[0195] Device Examples 10-11 provide an organic electroluminescent device, which differs from Device Example 1 only in that the main material of the light-emitting layer is different. The specific composition of the main material of the light-emitting layer is detailed in Table 4 below. Furthermore, when the main material of the light-emitting layer is composed of multiple compounds, the volume ratio between the compounds of each main material is the same. In addition, BD-2 is replaced with BD-1. Other structures, materials and preparation methods are the same as those in Device Example 1.

[0196] Performance testing:

[0197] The driving voltage, current efficiency, and lifetime LT90 of the organic electroluminescent devices provided above were tested. LT90 refers to the time required for the brightness to drop to 90% of the original brightness while maintaining the current density at an initial brightness of 1000 nits. The specific test results are shown in Table 4. The driving voltage, current efficiency, and LT90 are all relative values ​​(based on device example 10).

[0198] Table 4

[0199]

[0200] In summary, by designing the specific composition of the composition and the structure of the compounds in the composition, and by using this composition as the main material of the light-emitting layer of the OLED light-emitting device, the OLED light-emitting device has a lower driving voltage, higher current efficiency, and longer lifespan.

[0201] The present invention has been illustrated with the above embodiments to describe the detailed process flow of the present invention. However, the present invention is not limited to the above detailed process flow, that is, it does not mean that the present invention must rely on the above detailed process flow to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the 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 composition, characterized in that, The composition comprises at least a first compound and a second compound, wherein the first compound is selected from compounds represented by Formula A, the second compound is selected from compounds represented by Formula I, and the first compound is different from the second compound; Formula A; In Formula A, Ar1 and Ar2 are each independently selected from at least one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted biphenyl, wherein each of the substituted substituents is independently a deuterium atom. In the compound shown in Formula A, each hydrogen atom can be independently replaced by a deuterium atom; Formula I In Formula I, the Ar 11 Ar 12 Each is independently selected from any one of substituted or unsubstituted C6-C40 aryl groups or substituted or unsubstituted C12-C40 heteroaryl groups; The R 11 R 12 Each is independently selected from any one of substituted or unsubstituted C1-C6 straight-chain or branched alkyl groups, substituted or unsubstituted C6-C40 aryl groups, or substituted or unsubstituted C12-C40 heteroaryl groups; Ar 11 Ar 12 R 11 R 12 In this context, each of the substituents is independently selected from at least one of deuterium atom, C1-C6 straight-chain or branched alkyl group, C6-C20 aryl group, and C6-C20 heteroaryl group; The m and n are each independently selected from integers from 0 to 4; In the compound shown in Formula I, each hydrogen atom can be independently replaced by a deuterium atom.

2. The composition according to claim 1, characterized in that, The Ar 11 Ar 12 R 11 R 12 In this context, the C6-C40 aryl group is selected from any one of phenyl, biphenyl, naphthyl, phenanthryl, anthracene, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, triphenylene, fluoranyl, pyrene, perylene, spirofluorenyl, indo[a]fluorenyl, or hydrogenated benzo[a]anthryl; Preferably, the Ar 11 Ar 12 R 11 R 12 In this context, the C12~C40 heteroaryl groups are selected from any one of dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, and benzonaphthothiophenyl. Preferably, Ar 11 Ar 12 R 11 R 12 In the case where the substituent is a C6-C20 aryl group, the C6-C20 aryl group is preferably phenyl, naphthyl, or biphenyl. Preferably, Ar 11 Ar 12 R 11 R 12 In the case where the substituent is a C6-C20 heteroaryl, the C6-C20 heteroaryl is preferably dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, or naphthobenzothiophenyl. Preferably, the Ar 11 Selected from , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , Any one of them; Preferably, the Ar 12 Selected from , , , , , , , , , , , , , , , , Any one of them; Preferably, the R 11 R 12 Each is independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, , Any one of them.

3. The composition according to claim 1, characterized in that, The compound represented by Formula I is selected from any one of the following compounds, substituted or unsubstituted: ； The substitution refers to the fact that each hydrogen atom in the above compound can be independently replaced by a deuterium atom; Preferably, the compound represented by formula A is selected from any one of the following compounds, whether substituted or unsubstituted: ; The substitution refers to the fact that each hydrogen atom in the above compound can be independently replaced by a deuterium atom.

4. The composition according to claim 1, characterized in that, The compound represented by Formula I is selected from any one of the following compounds: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 ； Preferably, the compound represented by formula A is selected from any one of the following compounds: 、 、 、 、 、 、 、 、 、 、 。 5. The composition according to claim 1, characterized in that, The first compound is selected from the compound shown in Formula A, the second compound is selected from the compound shown in Formula I-1, and the first compound is different from the second compound; Formula I-1; In Equation I-1, Ar 111 for Ar 61 It is selected from at least one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted biphenyl, wherein each of the substituted substituents is independently a deuterium atom; Ar 121 It is selected from at least one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted biphenyl, wherein each of the substituted substituents is independently a deuterium atom; In the compound shown in Formula I-1, each hydrogen atom can be independently replaced by a deuterium atom.

6. The composition according to claim 1, characterized in that, With the sum of the volume percentage or mass percentage of the first compound and the second compound being 100%, the volume percentage or mass percentage of the first compound is 0.1% to 49%, preferably 10% to 40%, more preferably 10% to 30%, even more preferably 10% to 20%, and still more preferably 15% to 20%. Preferably, with the sum of the volume percentage or mass percentage of the first compound and the second compound being 100%, the volume percentage or mass percentage of the first compound is 51% to 95%, more preferably 60% to 95%, further preferably 70% to 95%, even more preferably 80% to 95%, and still more preferably 90% to 95%. Preferably, with the sum of the volume percentage or mass percentage of the first compound and the second compound being 100%, the volume percentage or mass percentage of the first compound is 70% to 90%, more preferably 75% to 85%; Preferably, the volume percentage or mass percentage of the first compound is 50%, with the sum of the volume percentage or mass percentage of the first compound and the second compound being 100%.

7. 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 organic thin film layer includes the composition according to any one of claims 1 to 6; Preferably, the organic thin film layer includes a light-emitting layer, and the light-emitting layer includes the composition described above.

8. The organic electroluminescent device according to claim 7, characterized in that, The light-emitting layer further includes a doping material, which comprises a compound having the structure shown in Formula II: Formula II; In formula II, R 21 R 22 and R 23 Each is independently selected from hydrogen, C1-C12 straight-chain or branched alkyl, C6-C12 cycloalkyl, -NAr 23 Ar 24 Any one of them; Ar 21 Ar 22 Ar 23 Ar 24 Each is independently selected from any one of substituted or unsubstituted C6-C20 aryl groups or substituted or unsubstituted C3-C20 heteroaryl groups; Ar 21 Ar 22 Ar 23 Ar 24 In this context, each of the substituents is independently selected from C1-C5 straight-chain or branched alkyl groups or C6-C12 aryl groups; Preferably, the Ar 21 Ar 22 Ar 23 Ar 24 Each independently selected , , , , , , , , , , , , , , , , Any of the following, with dashed lines representing connection points; Preferably, R 21 R 22 and R 23 Each is independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, or adamantyl; Preferably, the compound of formula II is selected from any one of the following compounds: 。 9. The organic electroluminescent device according to claim 7, characterized in that, The light-emitting layer further includes a doping material, which comprises a compound having the structure shown in Formula III: Formula III; Ⅲ, Ar 31 Ar 32 Ar 33 and Ar 34 Each is independently selected from any one of substituted or unsubstituted C6-C22 aryl groups or substituted or unsubstituted C12-C40 heteroaryl groups; R 31 Selected from any one of phenyl, naphthyl, or biphenyl; a is selected from 0 or 1; Ar 31 Ar 32 Ar 33 Ar 34 In this context, each of the substituents is independently selected from C1-C5 straight-chain or branched alkyl groups or C6-C12 aryl groups; Preferably, the Ar 31 Ar 32 Ar 33 and Ar 34 Each independently selected , , , , , , , , , Any one or at least two of the above, with dashed lines indicating connection sites; Preferably, the compound of formula III is selected from any one of the following compounds: 。 10. The organic electroluminescent device according to claim 7, characterized in that, The light-emitting layer further includes a doping material, which comprises a compound having the structure shown in Formula IV: Formula IV; In Equation IV, X1, X2, X3, and X4 are each independently selected from O, S, and -CR. 81 R 82 -NR 83 ; R 81 R 82 Each is independently selected from C1~C10 alkyl or C6~C15 aryl, R 81 and R 82 They can be connected in a ring using a single key; R 83 Selected from C1~C10 alkyl or C6~C15 aryl; R 61 ~R 76 Each is independently selected from H, D, F, cyano, C1-C10 alkyl, C1-C10 alkoxy, C6-C15 aryl, -NR 85 R 86 Any one of them; R 85 R 86 Each is independently selected from C1-C10 alkyl or C6-C15 aryl, and R 85 R 86 They can be connected in a ring using a single key; The R 61 ~R 76 When each is independently selected from C1~C10 alkyl groups, any two adjacent R groups 61 ~R 76 They can be directly connected to form a ring; The R 61 ~R 76 When each is independently selected from C6~C15 aryl groups, R 61 ~R 76 Can be used with R 61 ~R 76 The benzene rings they belong to are connected by -O-, -S-, and -CR-. 87 R 88 -、-NR 89 -Bridge, R 87 R 88 R 89 Each is independently selected from C1-C10 alkyl or C6-C15 aryl; Preferably, the compound of formula IV is selected from any one of the following compounds: 。

Images