A composition and organic electroluminescent device
Patent Information
- Application Number
- CN202611219558.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2026-08-12
- Publication Date
- 2026-10-27
AI Technical Summary
[0135]本发明中通过对组合物的具体组成进行设计,并采用此组合物作为OLED发光器件发光层材料,使得OLED发光器件具有较低的驱动电压、较高的电流效率和较长的寿命。
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Abstract
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 a simpler structure, various processing advantages, higher brightness, excellent viewing angle characteristics, faster response speed, and lower driving voltage. Therefore, they have been fully developed for use as light sources for flat panel displays (such as wall-mounted TVs) or as backlight units for displays, lighting fixtures, and advertising boards.
[0003] The structure of an organic light-emitting diode (OLED) 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 present invention aims to provide a composition and an organic electroluminescent device, wherein the composition is used as the light-emitting layer material of an OLED light-emitting device, thereby enabling the OLED light-emitting device to have a lower driving voltage, higher current efficiency and longer lifespan.
[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 a first component and a second component, wherein the first component comprises at least one of the compounds represented by Formula I:
[0008]
[0009] Formula I;
[0010] In Equation I, ring A is selected from In ring A, R1 and R2 are each independently selected from any one of C1~C12 alkyl and C6~C40 aryl, and R1 and R2 can be linked together by a single bond to form a ring;
[0011] Ring B is selected from or ;
[0012] The ring C is selected from benzene ring, naphthyl ring, dibenzofuran ring or 9,9-dimethyl-substituted fluorene ring;
[0013] In Formula I, Ar1 and Ar2 are each independently selected from any one of the C6~C40 aryl groups;
[0014] In the compound of formula I, each hydrogen atom can be independently substituted by at least one of a deuterium atom, a C1-C12 alkyl group, a C1-C12 alkoxy group, or a C6-C20 aryl group;
[0015] The second component includes at least one of the compounds shown in Formula II and Formula III:
[0016]
[0017] Formula II;
[0018]
[0019] Formula III;
[0020] In Equation II, Ar 601 Selected from , , , , , , , , Any one of them; Ar 602 Selected from -H, , , , , , , , , Any one of the following, the dashed line indicates the connection site; in the compound of formula II, each hydrogen atom can be independently replaced by a deuterium atom;
[0021] In Equation III, Ar 11 Ar 12 Each is independently selected from any one of substituted or unsubstituted C6-C40 aryl groups and substituted or unsubstituted C12-C40 heteroaryl groups; R a R bEach 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 a R b In the formula III compound, each of the substituents is independently selected from at least one of C1-C6 straight-chain or branched alkyl, C6-C20 aryl, and C6-C20 heteroaryl; m and n are each independently selected from integers from 0 to 4; and each of the hydrogen atoms in the compound III can be independently replaced by a deuterium atom.
[0022] The composition of the present invention includes a first component and a second component, wherein the first component includes at least one of the compounds shown in Formula I, and the second component includes at least one of the compounds shown in Formula II and Formula III. The two components work together as the main material of the light-emitting layer of an OLED light-emitting device, thereby enabling the OLED light-emitting device to have a lower driving voltage, higher current efficiency, and longer lifespan.
[0023] In this invention, "D" represents a deuterium atom. Unless otherwise specified, "H" and "hydrogen" both represent "protium".
[0024] Preferably, in Formula I, the C6-C40 aryl group is selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, triphenylene, fluoranthyl, anthracene, and phenanthrenebenzophenanthryl.
[0025] Preferably, in Formula I, the C1-C12 alkyl group is selected from any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, n-pentyl, n-hexyl, cyclohexyl, and adamantyl.
[0026] Preferably, in Formula I, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, and adamantoxy.
[0027] Preferably, in Formula I, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, and triphenylene.
[0028] Preferably, each hydrogen atom in the compound of formula I can be independently substituted by at least one of deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, propoxy, phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, and triphenylene.
[0029] Preferably, the compound represented by Formula I is selected from any one of the following substituted or unsubstituted compounds:
[0030]
[0031]
[0032]
[0033]
[0034]
[0035]
[0036]
[0037]
[0038]
[0039]
[0040]
[0041]
[0042] ;
[0043] The substitution refers to the replacement of at least one hydrogen atom in the above compound with a deuterium atom.
[0044] Preferably, the compound represented by Formula I is selected from any one of the following compounds:
[0045] .
[0046] Preferably, the compound represented by Formula II is selected from any one of the following substituted or unsubstituted compounds:
[0047] ;
[0048] The substitution refers to the replacement of at least one hydrogen atom in the above compound with a deuterium atom.
[0049] Preferably, the compound represented by Formula II is selected from any one of the following compounds:
[0050] .
[0051] Preferably, in Formula III, 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.
[0052] Preferably, in Formula III, the C12~C40 heteroaryl group is selected from any one of dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, and benzonaphthothiophenyl.
[0053] Preferably, in Formula III, the C1-C6 straight-chain or branched alkyl group is selected from any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, and n-hexyl.
[0054] Preferably, in Formula III, the C6-C20 aryl group is selected from any one of phenyl, biphenyl, naphthyl, phenanthryl, anthracene, fluorenyl, triphenylene, and fluoranthracene.
[0055] Preferably, in Formula III, the C6~C20 heteroaryl groups are selected from any one of carbazolyl, dibenzofuranyl, and dibenzothiophenel.
[0056] Preferably, in Formula III, the Ar 11 Ar 12 Each independently selected , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , Any of the following, with dashed lines representing connection points.
[0057] Preferably, in formula III, the R a R b Each is independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, , Any of the following, with dashed lines representing connection points.
[0058] Preferably, the compound represented by Formula III is selected from any one of the following substituted or unsubstituted compounds:
[0059] ;
[0060] The substitution refers to the replacement of at least one hydrogen atom in the above compound with a deuterium atom.
[0061] Preferably, the compound represented by Formula III is the compound represented by Formula III-1:
[0062]
[0063] Formula III-1;
[0064] In Equation III-1, R a R b Ar 12 m and n have the same range of limitation as in Equation III;
[0065] In Equation III-1, Ar 111 Selected from , , , , , , , , , , Any of the following, with dashed lines representing connection points;
[0066] In the compound of formula III-1, each hydrogen atom can be independently replaced by a deuterium atom.
[0067] Preferably, in formula III-1, Ar 12 Selected from , , , , , , , , , , Any of the following, with dashed lines representing connection points.
[0068] Preferably, the compound represented by Formula III-1 is selected from any one of the following compounds:
[0069] .
[0070] Preferably, the volume ratio of the first component to the second component is 5~60:40~95, more preferably 10~50:50~90.
[0071] Preferably, the composition further comprises a third component, the third component comprising at least one of the compounds represented by formula IIBD, formula IIIBD, and formula IVBD;
[0072]
[0073] Mode BD;
[0074] Mode In BD, 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;
[0075] Mode In BD, 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;
[0076] Mode In BD, Ar 21 Ar 22 Ar 23 Ar 24 The substituents described herein are each 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).
[0077]
[0078] Mode BD;
[0079] Mode In BD, 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;
[0080] Mode In BD, R 31 Selected from any one of H, phenyl, naphthyl, or biphenyl;
[0081] Mode In BD, 'a' is selected from 0 or 1;
[0082] Mode In BD, Ar 31 Ar 32 Ar 33 Ar 34 The substituents described herein are each 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).
[0083]
[0084] Mode BD;
[0085] Mode In BD, X1, X2, X3, and X4 are each independently selected from O, S, and CR. 81 R 82 NR 83 ;
[0086] Mode In BD, 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;
[0087] Mode In BD, 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;
[0088] Mode In BD, R 61 ~R 76 Each is independently selected from H, D, F, cyano, 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;
[0089] Mode In BD, 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) aryl, and R 85 R 86 They can be connected in a ring using a single key;
[0090] Mode In BD, 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;
[0091] Mode In BD, the R 61 ~R76 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.
[0092] Examples are given below:
[0093] R 62 Selected from NR 85 R 86 And R 85 R 86 When both are selected from ethyl groups, the IVBD compound can be as follows:
[0094] .
[0095] 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 IVBD compound structure is as follows, formed by single-bond linkages:
[0096] .
[0097] R 62 Selected from NR 85 R 86 And R 85 R 86 When both are selected from phenyl groups, the structure of the IVBD compound is as follows:
[0098] .
[0099] R 62 Selected from NR 85 R 86 And R 85 R 86 All are selected from phenyl, and R 85 R86 The IVBD compound structure is as follows, formed by single-bond linkages:
[0100] .
[0101] The R 61 ~R 76 When each alkyl group is independently selected from C1-C10, any two adjacent R 61 ~R 76 They can be directly connected to form a ring; the R 61 ~R 76 When each aryl group is independently selected from C6-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;
[0102] Examples are given below:
[0103] R 61 R 62 When both are selected from ethyl groups, the structure of the IVBD compound is as follows:
[0104] .
[0105] R 61 R 62 All are selected from ethyl groups, and R 61 R 62 The structure of an IVBD compound can be obtained by direct cyclic linkage as follows:
[0106] .
[0107] R 61 R 62 When both are selected from phenyl groups, the structure of the IVBD compound is as follows:
[0108] .
[0109] R 61 Selected from phenyl, R 62 Selected from H, the structure of the IVBD compound is as follows:
[0110] .
[0111] 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 the IVBD compound can be as follows:
[0112] .
[0113] Based on the use of a first component and a second component as the main material of the light-emitting layer, this invention further introduces a third component as the dopant material of the light-emitting layer. The resulting composition is used as the light-emitting layer material of an organic electroluminescent device, which enables the organic electroluminescent device to have a lower driving voltage, higher current efficiency and longer service life.
[0114] Preferably, formula In BD, the Ar 21 Ar 22 Ar 23 Ar 24 Each independently selected , , , , , , , , , , , , , , , , Any of the following, with dashed lines representing connection points.
[0115] Preferably, formula In BD, 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.
[0116] Preferably, the formula The compound shown in BD is selected from any one of the following compounds:
[0117] .
[0118] Preferably, formula In BD, the Ar 31 Ar 32 Ar 33 and Ar 34 Each independently selected , , , , , , , , , Any of the following, with dashed lines representing connection points.
[0119] Preferably, the formula The compound shown in BD is selected from any one of the following compounds:
[0120] .
[0121] Preferably, in formula IVBD, 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.
[0122] Preferably, in formula IVBD, the C1~C10 alkoxy groups are selected from any one of methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, and adamantoxy.
[0123] Preferably, in formula IVBD, the C6-C15 aryl group is selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, phenanthryl, and anthracene.
[0124] Preferably, the compound represented by formula IVBD is selected from any one of the following compounds:
[0125] .
[0126] It should be noted that the present invention does not impose any special restrictions on the preparation methods of the compounds shown in Formula I, Formula II, Formula III, Formula IV, Formula IIBD, Formula IIIBD, and Formula IVBD, and the preparation methods commonly used in the art are all applicable.
[0127] Preferably, with the total volume fraction of the first component, the second component, and the third component being 100%, the volume fraction of the third component is 0.1% to 40%, more preferably 0.5% to 15%, more preferably 1% to 10%, and even more preferably 3%.
[0128] 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;
[0129] The organic thin film layer comprises the composition as described in the first aspect.
[0130] Preferably, the organic thin film layer includes a light-emitting layer, and the light-emitting layer includes the composition described above.
[0131] Preferably, the organic layer further includes a hole layer, which includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer. The present invention does not impose any special restrictions on the specific material selection for the hole layer; commonly used hole layer materials in the art are applicable.
[0132] Preferably, the organic layer further includes an electronic layer, which includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer. The present invention does not impose any special restrictions on the specific material selection for the electronic layer; commonly used materials for electronic layers in the art are applicable.
[0133] Thirdly, the present invention provides a display device comprising the organic electroluminescent device as described in the second aspect.
[0134] Compared with the prior art, the present invention has the following beneficial effects:
[0135] In this invention, by designing the specific composition of the composition and using this composition as the light-emitting layer material of the OLED light-emitting device, the OLED light-emitting device has a lower driving voltage, higher current efficiency and longer lifespan. Detailed Implementation
[0136] 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.
[0137] The specific structures of some of the compounds used in the following device embodiments and device comparative examples are shown below:
[0138]
[0139] .
[0140] Device Example 1
[0141] This embodiment of the device provides an organic electroluminescent device. The structure of the organic electroluminescent device is ITO / HT (40nm) / light-emitting layer host material: BD-2 (3%) (30nm) / TPBI (30nm) / LiF (0.5nm) / Al (150nm). The light-emitting layer host material: BD-2 (3%) means that the volume ratio of the light-emitting layer host material to the dopant material BD-2 is 97:3. In this embodiment, the light-emitting layer host material is composed of a first component and a second component in a volume ratio of 1:9, wherein the first component is P1 and the second component is BH2.
[0142] The fabrication method of the above-mentioned organic electroluminescent device is as follows:
[0143] (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 binding ability with hole transport layer.
[0144] (2) Place the glass substrate in a vacuum chamber and evacuate it to 1×10⁻⁶. -6 ~1×10 -5 Pa, a mixture of D4-HTSP1 and D8-HTSP1 was vacuum-deposited on the anode. By placing these two compounds in different evaporation sources and controlling the temperature of the evaporation sources to control the evaporation rate of the two compounds, a mixture with a desired volume ratio of 1:1 was obtained and used as the HT (hole transport) layer of the device. The total evaporation rate of the two compounds was 0.01 nm / s, and the evaporation film thickness was 40 nm.
[0145] (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 light-emitting layer host material and a doping material. The light-emitting layer host material is composed of a first component and a second component. The first component is compound P1, the second component is BH2, and the doping material is BD-2. The volume ratio of the first component and the second component is 1:9, and the volume ratio of the light-emitting layer host material to the doping material is 97:3. When the light-emitting layer host material is two or more compounds, different compounds are placed in different evaporation sources, and the deposition rate of different compounds is controlled so that the mixture with a specified volume ratio is used as the light-emitting layer host material in the organic electroluminescent device.
[0146] (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.
[0147] (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.
[0148] Device Examples 2-3
[0149] Device Examples 2 and 3 each provide an organic electroluminescent device. The only difference between them and Device Example 1 is 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 1 below. The volume ratio of the first component and the second component in the main material of the light-emitting layer is 1:9, and the volume ratio of the main material of the light-emitting layer to the doped material is 97:3. Other structures, materials and preparation methods are the same as those in Device Example 1.
[0150] Device Comparison Examples 1-2
[0151] Comparative Examples 1 and 2 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 1 below, and the volume ratio of the main material of the light-emitting layer to the doped material is 97:3; other structures, materials and preparation methods are the same as those in Device Example 1.
[0152] Performance testing:
[0153] 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 1. The driving voltage, current efficiency, and LT90 are all relative values (based on device example 1).
[0154] Table 1
[0155]
[0156] Note: In the table above, " / " indicates that the light-emitting layer material of the embodiment or comparative example of the device does not contain this component.
[0157] As can be seen from the table above, the present invention uses a specific composition as the light-emitting layer material of the OLED light-emitting device, which enables the OLED light-emitting device to have a lower driving voltage, higher current efficiency and longer lifespan.
[0158] Device Examples 4-7, Device Comparative Examples 3-4
[0159] Device Examples 4-7 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, the volume ratio of the first component and the second component in the main material of the light-emitting layer is 1:9, and the volume ratio of the main material of the light-emitting layer to the doped material is 97:3. Other structures, materials and preparation methods are the same as those in Device Example 1.
[0160] Comparative Examples 3 and 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. The specific composition of the main material of the light-emitting layer is detailed in Table 2 below. Furthermore, the volume ratio of the main material of the light-emitting layer to the doped material is 97:3. Other structures, materials, and preparation methods are the same as those in Device Example 1.
[0161] Performance testing:
[0162] 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 4).
[0163] Table 2
[0164]
[0165] Note: In the table above, " / " indicates that the light-emitting layer material of the embodiment or comparative example of the device does not contain this component.
[0166] As can be seen from the table above, the present invention uses a specific composition as the light-emitting layer material of the OLED light-emitting device, which enables the OLED light-emitting device to have a lower driving voltage, higher current efficiency and longer lifespan.
[0167] Device Example 8, Device Comparative Examples 5-6
[0168] Device Example 8 provides 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, the volume ratio of the first component and the second component in the main material of the light-emitting layer is 1:9, and the volume ratio of the main material of the light-emitting layer to the doped material is 97:3. In addition, BD-2 is replaced with BD-1. Other structures, materials and preparation methods are the same as those in Device Example 1.
[0169] Comparative Examples 5 and 6 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, the volume ratio of the main material of the light-emitting layer to the doped material is 97:3. In addition, BD-2 is replaced with BD-1. Other structures, materials and preparation methods are the same as those in Device Example 1.
[0170] Performance testing:
[0171] 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 8).
[0172] Table 3
[0173]
[0174] Note: In the table above, " / " indicates that the light-emitting layer material of the embodiment or comparative example of the device does not contain this component.
[0175] As can be seen from the table above, the present invention uses a specific composition as the light-emitting layer material of the OLED light-emitting device, which enables the OLED light-emitting device to have a lower driving voltage, higher current efficiency and longer lifespan.
[0176] Device Examples 9-11, Device Comparative Examples 7-8
[0177] Device Examples 9-11 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 4 below. Furthermore, the volume ratio of the first component and the second component in the main material of the light-emitting layer is 5:5, and the volume ratio of the main material of the light-emitting layer to the doped material is 97:3. In addition, BD-2 is replaced with BD-1. The other structures, materials and preparation methods are the same as those in Device Example 1.
[0178] Comparative Examples 7 and 8 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 4 below. Furthermore, the volume ratio of the main material of the light-emitting layer to the doped material is 97:3. In addition, BD-2 is replaced with BD-1. Other structures, materials and preparation methods are the same as those in Device Example 1.
[0179] Performance testing:
[0180] 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 9).
[0181] Table 4
[0182]
[0183] Note: In the table above, " / " indicates that the light-emitting layer material of the embodiment or comparative example of the device does not contain this component.
[0184] As can be seen from the table above, the present invention uses a specific composition as the light-emitting layer material of the OLED light-emitting device, which enables the OLED light-emitting device to have a lower driving voltage, higher current efficiency and longer lifespan.
[0185] 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 a first component and a second component, wherein the first component comprises at least one of the compounds represented by Formula I: Formula I; In Equation I, ring A is selected from In ring A, R1 and R2 are each independently selected from any one of C1~C12 alkyl and C6~C40 aryl, and R1 and R2 can be linked together by a single bond to form a ring; Ring B is selected from or ; The ring C is selected from benzene ring, naphthyl ring, dibenzofuran ring or 9,9-dimethyl-substituted fluorene ring; In Formula I, Ar1 and Ar2 are each independently selected from any one of the C6~C40 aryl groups; In the compound of formula I, each hydrogen atom can be independently substituted by at least one of a deuterium atom, a C1-C12 alkyl group, a C1-C12 alkoxy group, or a C6-C20 aryl group; The second component includes at least one of the compounds shown in Formula II and Formula III: Formula II; Formula III; In Equation II, Ar 601 Selected from , , , , , , , , Any one of them; Ar 602 Selected from -H, , , , , , , , , Any one of the following, the dashed line indicates the connection site; in the compound of formula II, each hydrogen atom can be independently replaced by a deuterium atom; In Equation III, Ar 11 Ar 12 Each is independently selected from any one of substituted or unsubstituted C6-C40 aryl groups and substituted or unsubstituted C12-C40 heteroaryl groups; R a R b 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 a R b In the formula III compound, each of the substituents is independently selected from at least one of C1-C6 straight-chain or branched alkyl, C6-C20 aryl, and C6-C20 heteroaryl; m and n are each independently selected from integers from 0 to 4; and each of the hydrogen atoms in the compound III can be independently replaced by a deuterium atom.
2. The composition according to claim 1, characterized in that, In Formula I, the C6-C40 aryl group is selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, triphenylene, fluoranthyl, anthracene, and phenanthrenebenzophenanthrene; Preferably, in Formula I, the C1-C12 alkyl group is selected from any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, n-pentyl, n-hexyl, cyclohexyl, and adamantyl. Preferably, in Formula I, the C1~C12 alkoxy groups are selected from any one of methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, and adamantoxy. Preferably, in Formula I, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, and triphenylene. Preferably, each hydrogen atom in the compound of formula I can be independently substituted by at least one of deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, propoxy, phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, and triphenylene. Preferably, the compound represented by Formula I is selected from any one of the following substituted or unsubstituted compounds: ; The substitution refers to the replacement of at least one hydrogen atom in the above compound with a deuterium atom; Preferably, the compound represented by Formula I is selected from any one of the following compounds: 。 3. The composition according to claim 1, characterized in that, The compound represented by Formula II is selected from any one of the following substituted or unsubstituted compounds: ; The substitution refers to the replacement of at least one hydrogen atom in the above compound with a deuterium atom; Preferably, the compound represented by Formula II is selected from any one of the following compounds: 。 4. The composition according to claim 1, characterized in that, In Formula III, 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, in Formula III, the C12~C40 heteroaryl group is selected from any one of dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, and benzonaphthothiophenyl; Preferably, in Formula III, the C1-C6 straight-chain or branched alkyl group is selected from any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, and n-hexyl; Preferably, in Formula III, the C6-C20 aryl group is selected from any one of phenyl, biphenyl, naphthyl, phenanthryl, anthracene, fluorenyl, triphenylene, and fluoranthracene. Preferably, in Formula III, the C6~C20 heteroaryl group is selected from any one of carbazole, dibenzofuran, and dibenzothiophene. Preferably, in Formula III, the Ar 11 Ar 12 Each independently selected , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , Any of the following, with dashed lines representing connection points; Preferably, in formula III, the R a R b Each is independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, , Any of the following, with dashed lines representing connection points; Preferably, the compound represented by Formula III is selected from any one of the following substituted or unsubstituted compounds: ; The substitution refers to the replacement of at least one hydrogen atom in the above compound with a deuterium atom.
5. The composition according to claim 1, characterized in that, The compound represented by Formula III is the same as the compound represented by Formula III-1 below: Formula III-1; In Equation III-1, R a R b Ar 12 m and n have the same range of limitation as in Equation III; In Equation III-1, Ar 111 Selected from , , , , , , , , , , Any of the following, with dashed lines representing connection points; In the compound of formula III-1, each hydrogen atom can be independently replaced by a deuterium atom; Preferably, in formula III-1, Ar 12 Selected from , , , , , , , , , , Any of the following, with dashed lines representing connection points; Preferably, the compound represented by Formula III-1 is selected from any one of the following compounds: 。 6. The composition according to claim 1, characterized in that, The volume ratio of the first component to the second component is 5~60:40~95, preferably 10~50:50~90.
7. The composition according to claim 1, characterized in that, The composition further includes a third component, which includes at least one of the compounds represented by formula IIBD, formula IIIBD, and formula IVBD; Mode BD; Mode In BD, 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; Mode In BD, 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; Mode In BD, Ar 21 Ar 22 Ar 23 Ar 24 The substituents described herein are each independently selected from C1-C5 straight-chain or branched alkyl groups or C6-C12 aryl groups; Mode BD; Mode In BD, 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; Mode In BD, R 31 Selected from any one of H, phenyl, naphthyl, or biphenyl; Mode In BD, 'a' is selected from 0 or 1; Mode In BD, Ar 31 Ar 32 Ar 33 Ar 34 The substituents described herein are each independently selected from C1-C5 straight-chain or branched alkyl groups or C6-C12 aryl groups; Mode BD; Mode In BD, X1, X2, X3, and X4 are each independently selected from O, S, and CR. 81 R 82 NR 83 ; Mode In BD, 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; Mode In BD, R 83 Selected from C1~C10 alkyl or C6~C15 aryl; Mode In BD, 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; Mode In BD, 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; Mode In BD, 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; Mode In BD, 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.
8. The composition according to claim 7, characterized in that, Mode In BD, the Ar 21 Ar 22 Ar 23 Ar 24 Each independently selected , , , , , , , , , , , , , , , , Any of the following, with dashed lines representing connection points; Preferably, formula In BD, 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 formula The compound shown in BD is selected from any one of the following compounds: ; Preferably, formula In BD, the Ar 31 Ar 32 Ar 33 and Ar 34 Each independently selected , , , , , , , , , Any of the following, with dashed lines representing connection points; Preferably, the formula The compound shown in BD is selected from any one of the following compounds: ; Preferably, in formula IVBD, 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. Preferably, in formula IVBD, the C1~C10 alkoxy groups are selected from any one of methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, and adamantoxy. Preferably, in formula IVBD, the C6-C15 aryl group is selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, phenanthryl, and anthraceneyl. Preferably, the compound represented by formula IVBD is selected from any one of the following compounds: 。 9. The composition according to claim 7, characterized in that, With the total volume fraction of the first component, the second component, and the third component being 100%, the volume fraction of the third component is 0.1% to 40%, preferably 0.5% to 15%, more preferably 1% to 10%, and even more preferably 3%.
10. 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 comprises the composition according to any one of claims 1 to 9; Preferably, the organic thin film layer includes a light-emitting layer, and the light-emitting layer includes the composition described above.