An organic electroluminescent material and its application
By bonding a specific structure in the first body material of the organic electroluminescent material and matching the second body material, the problems of existing material stability and carrier mobility imbalance are solved, and an organic electroluminescent device with a longer life, low driving voltage and high efficiency are achieved.
Patent Information
- Application Number
- CN202310111032.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2023-01-20
- Publication Date
- 2025-06-24
- Estimated Expiration
- 2043-01-20
AI Technical Summary
The existing organic electroluminescent materials have low stability and unbalanced carrier mobility, resulting in a short life of organic electroluminescent diodes, which limits their application.
An organic electroluminescent material comprising a first host material and a second host material is adopted, and the compound of the first host material is used as the main material of the light emitting layer by bonding a specific structure to the main ring structure while cooperating with the compound of the second host material.
The stability of organic electroluminescent compounds and the balance of carrier mobility is improved, the life of organic electroluminescent devices is extended, the driving voltage is reduced and the efficiency is improved.
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Figure CN116162069B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to the field of display technologies, and particularly to an organic electroluminescent material and its application. Background Art
[0002] An organic electroluminescent device (OLED) converts electrical energy into light by applying electricity to an organic electroluminescent material, and generally includes an anode, a cathode, and an organic layer formed between these two electrodes. The organic layer of the organic EL device may include a hole injection layer, a hole transport layer, a hole assisting layer, a light emitting assisting layer, an electron blocking layer, a light emitting layer (containing a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. The materials used in the organic layer can be classified into hole injection materials, hole transport materials, hole assisting materials, light emitting assisting materials, electron blocking materials, light emitting materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. depending on their functions. In the organic EL device, holes from the anode and electrons from the cathode are injected into the light emitting layer by applying a voltage, and excitons with high energy are generated by the recombination of holes and electrons. The organic light emitting compound emits light by moving energy to the excited state and by the energy when the organic light emitting compound returns from the excited state to the ground state.
[0003] Currently, problems such as the short lifespan of organic electroluminescent diodes caused by the low stability of organic functional materials and the imbalance of carrier mobilities seriously limit the application of organic electroluminescent diodes. Summary of the Invention
[0004] The purpose of the present invention is to overcome the defect that the lifespan of organic electroluminescent diodes is short due to the low stability of existing organic electroluminescent materials and the imbalance of carrier mobilities, and further provide an organic electroluminescent material and its application.
[0005] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can include at least one first host material and a second host material. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole assisting material, a light emitting assisting material, an electron blocking material, a light emitting material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc. Preferably, the organic electroluminescent material is used as the host material of the light emitting layer.
[0006] Definition of substituent terms in the present invention:
[0007] As used in the present invention, the term "halogen" may include fluorine, chlorine, bromine, or iodine.
[0008] As used in the present invention, the term "C1-C30 alkyl" refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 30 carbon atoms, and examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.
[0009] As used in the present invention, the term "C3-C30 cycloalkyl" refers to a monocyclic hydrocarbon or polycyclic hydrocarbon derived from a cyclic main chain having 1 to 30 carbon atoms, and the cycloalkanes may include cyclopropyl, cyclobutyl, adamantyl, etc.
[0010] In the present invention, aryl and arylene include monocyclic, polycyclic or fused-ring aryl, the rings may be interrupted by short non-aromatic units, and may include a spiro structure. Aryl includes, but is not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, fluorenyl, spirobifluorenyl, etc. Arylene includes, but is not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthrylene, fluorenylene, spirobifluorenylene, etc.
[0011] In the present invention, heteroaryl and heteroarylene include monocyclic, polycyclic or fused-ring heteroaryl, the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, and sulfur. Heteroaryl includes, but is not limited to, furyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and their derivatives, etc.; heteroarylene includes, but is not limited to, furylene, phenylthioylene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazanylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, benzofurylene, benzothienylene, isobenzofurylene, dibenzofurylene, dibenzothienylene, benzimidazolylene, benzothiazolylene, benzisothiazolylene, benzisoxazolylene, benzoxazolylene, isoindolylene, indolylene, indazolylene, benzothiadiazolylene, quinolinylene, isoquinolinylene, cinnolinylene, quinazolinylene, quinoxalinylene, carbazolylene, phenoxazinylene, phenothiazinylene, phenanthridinylene, benzodioxolylene, dihydroacridinylene, and their derivatives, etc.
[0012] As used in the present invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The position is not limited to a specific position as long as the hydrogen at that position can be replaced by a substituent. When there are two or more substituents, the two or more substituents may be the same or different. As used in the present invention, unless otherwise specified, a hydrogen atom includes protium, deuterium, and tritium.
[0013] In the present invention, in the definition of a group, the range of the number of carbon atoms is defined, and the number of carbon atoms is any integer within the defined range. For example, C6-C30 aryl means that the number of carbon atoms of the aryl can be any integer within the range included in 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25, or 30, etc.
[0014] The solution adopted in the present invention is as follows:
[0015] An organic electroluminescent material, the organic electroluminescent material comprising a first host material and a second host material, the first host material comprising a compound represented by formula (I):
[0016]
[0017] Wherein, X is selected from O, S, Se, NAr, CR 6 R 7 ;
[0018] R 1 is -L 1 Ar 1 R 2 is -L 2 Ar 2 R 3 is -L 3 Ar 3 ;
[0019] Ar is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl,
[0020] R 6 R 7 each independently is selected from a hydrogen atom, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,
[0021] L 1 -L 3 each independently is selected from a linking bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
[0022] Ar 1 -Ar 3 Each independently selected from hydrogen, deuterium, protium, tritium, halogen, cyano, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, wherein Ar 1 -Ar 3 at least one of which is a structure represented by formula (II),
[0023]
[0024] R 4 is —L 4 Ar 4 R 5 is —L 5 Ar 5 ,
[0025] wherein, L 4 -L 5 Each independently selected from a linking bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
[0026] Ar 4 -Ar 5 Each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C60 heteroaryl;
[0027] The second host material is a compound represented by formula (2):
[0028]
[0029] wherein, X 1 , X 2 Each independently selected from N or CR, and R is selected from hydrogen or deuterium;
[0030] L is selected from a linking bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
[0031] Ar 8 , Ar 9 Each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
[0032] The substituents in the substituted C1-C30 alkyl group, substituted C3-C30 cycloalkyl group, substituted C5-C60 aryl group, substituted C3-C60 heteroaryl group, substituted C1-C20 alkyl group, substituted C6-C30 aryl group, substituted C3-C30 heteroaryl group, substituted C6-C60 arylamino group, substituted C3-C60 heteroarylamino group, substituted C6-C60 aryl group, substituted C3-C60 heteroaryl group, substituted C6-C30 arylene group, and substituted C3-C30 heteroarylene group are selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl group, C3-C30 cycloalkyl group, C6-C30 aryl group, and C3-C30 heteroaryl group.
[0033] Preferably, in the second host material, L is a linking bond; Ar 8 , Ar 9 are each independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, fluorenyl, dimethylfluorenyl, spirobifluorenyl, fluoranthenyl, diphenylfluorenyl, benzyldimethylfluorenyl, benzylbiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenylcarbazolyl, dipyridyl, pyrimidinyl, and triazinyl.
[0034] Preferably, in the second host material, X 1 , X 2 are each independently selected from CR, where R is selected from hydrogen or deuterium;
[0035] alternatively, X1 is selected from N, and X 2 is selected from CR, where R is selected from hydrogen or deuterium.
[0036] Preferably, the compound represented by formula (2) has any of the following structures:
[0037]
[0038]
[0039]
[0040]
[0041]
[0042]
[0043] In the present invention represents a linking bond, and the linking bond can be a single bond.
[0044]
[0045] It is understandable that in the present invention, R 1 can be substituted on ring B, can also be substituted on ring C, and R 2 can be substituted on ring D, and R 3 can be substituted on ring E.
[0046] Preferably, in the first host material, L 1 -L 3 is selected from a linking bond, a C6-C30 arylene group, and Ar 1 -Ar 3 one of them is the structure shown in formula (II), and the remaining two are selected from hydrogen and C6-C30 aryl groups;
[0047] Optionally, L 1 -L 3 is selected from a linking bond, a C6-C30 arylene group, and Ar 1 -Ar 3 two of them are the structures shown in formula (II), and the remaining one is selected from hydrogen and C6-C30 aryl groups.
[0048] Preferably, in the first host material, Ar is selected from C6-C30 aryl groups and C3-C30 heteroaryl groups;
[0049] Preferably, Ar is selected from phenyl, naphthyl, biphenyl, terphenyl, triphenylene, anthryl, dibenzofuranyl, dibenzothiophenyl;
[0050] R6 and R7 are each independently selected from C1-C5 alkyl groups and C6-C30 aryl groups;
[0051] L 4 -L 5 are each independently selected from a linking bond and a C6-C30 arylene group;
[0052] Optionally, L 4 -L 5 are each independently selected from a linking bond, phenylene, and naphthylene. Further optionally, L 4 -L 5 are each independently selected from a linking bond;
[0053] Ar 4 -Ar 5 are each independently selected from C6-C30 aryl groups and C3-C30 heteroaryl groups;
[0054] Optionally, Ar 4 -Ar 5 are each independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, Group, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, triphenylenyl, dimethylfluorenyl, spirobifluorenyl, fluoranthenyl, carbazolyl, phenylcarbazolyl, diphenylfluorenyl, benzyldimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, pyridyl, pyrimidyl, triazinyl.
[0055] Preferably, Ar 4 and Ar 5 are each independently selected from the structures represented by the following formula (III) or formula (IV):
[0056]
[0057] R T1 -R T6 are each independently selected from hydrogen, deuterium, halogen, cyano, C1-C30 alkyl, C7-C30 aralkyl, C6-C30 aryl, C3-C30 heteroaryl, C4-C30 heteroaralkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C3-C30 cycloalkenyl, C1-C30 alkoxy, C6-C30 aryloxy; or, R T1 -R T5 adjacent to each other are fused to form ring A, and the ring A is selected from C6-C30 aryl;
[0058] Preferably, the ring A is selected from phenyl, naphthyl, and phenanthryl;
[0059] Y is selected from O, S, NAr, CR 6 R 7 ;
[0060] When there are multiple R T1 -R T6 , R T1 -R T6 are each independent of one another and may be the same or different;
[0061] wherein the definitions of Ar, R 6 , and R 7 are as described above.
[0062]
[0063] It can be understood that in the present invention, the La bond can be substituted on ring F or on ring H; R T6 can be substituted on ring F or on ring H.
[0064] Preferably, in the first host material, the compound represented by formula (I) has the structure represented by any one of Chemical Formula 1-1 to Chemical Formula 1-17:
[0065]
[0066]
[0067] wherein R 1 -R 7 、L 1 -L 3 、Ar are defined as described above.
[0068] Preferably, R 1 -R 3 are each independently selected from hydrogen; R 6 、R 7 are each independently selected from C1-C5 alkyl groups, preferably, R 6 、R 7 are each independently selected from methyl, ethyl; R 4 is —L 4 Ar 4 ,R 5 is —L 5 Ar 5 ,L 4 -L 5 are each independently selected from a linking bond, C6-C30 arylene groups;
[0069] Optionally, L 4 -L 5 are each independently selected from a linking bond, phenylene, naphthylene, and further optionally, L 4 -L 5 are each independently selected from a linking bond;
[0070] Ar 4 -Ar 5 are each independently selected from C6-C30 aryl groups, C3-C30 heteroaryl groups;
[0071] Optionally, Ar 4 -Ar 5 are each independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, anthryl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, triphenylene, dimethylfluorenyl, spirobifluorenyl, fluoranthenyl, carbazolyl, phenylcarbazolyl, diphenylfluorenyl, benzyldimethylfluorenyl, benzyldiphenylfluorenyl, benzospirobifluorenyl, pyridyl, pyrimidinyl, triazinyl.
[0072] Preferably, L 1 -L 3 are each independently selected from a linking bond, C6-C30 arylene groups, preferably, L 1 -L 3 are each independently selected from a linking bond, phenylene, naphthylene, triphenylene, biphenylene; further optionally, L 1Selected from linking groups, L 2 Selected from phenylene, naphthylene, terphenylenylene, biphenylenylene, L 3 is a linking group;
[0073] Ar is selected from aryl groups having 6 to 30 carbon atoms;
[0074] The aryl group having 6 to 30 carbon atoms is selected from phenyl, naphthyl, biphenyl.
[0075] Preferably, in the first host material, the compound represented by formula (I) has any of the following structures:
[0076]
[0077]
[0078]
[0079]
[0080]
[0081]
[0082]
[0083]
[0084]
[0085]
[0086]
[0087]
[0088]
[0089]
[0090]
[0091]
[0092]
[0093]
[0094]
[0095]
[0096]
[0097]
[0098]
[0099]
[0100]
[0101]
[0102]
[0103]
[0104]
[0105]
[0106]
[0107]
[0108]
[0109]
[0110]
[0111]
[0112] Preferably, the mass ratio of the compound represented by formula (1) to the compound represented by formula (2) is 1:9 - 9:1;
[0113] Preferably, the mass ratio of the compound represented by formula (1) to the compound represented by formula (2) is 2:8 - 8:2;
[0114] More preferably, the mass ratio of the compound represented by formula (1) to the compound represented by formula (2) is 3:7 - 7:3;
[0115] Further preferably, the mass ratio of the compound represented by formula (1) to the compound represented by formula (2) is 4:6 - 6:4.
[0116] The present invention also provides an application of the above-mentioned organic electroluminescent material in the preparation of optical devices.
[0117] Preferably, the optical device includes any one of an organic light-emitting device, an organic field-effect transistor, an organic thin-film transistor, an organic light-emitting transistor, an organic integrated circuit, an organic solar cell, an organic field quenching device, a light-emitting electrochemical cell, an organic laser diode, or an organic photoreceptor.
[0118] The present invention also provides an organic light-emitting device, which includes an anode and a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes the organic light-emitting material as described above. Preferably, the light-emitting layer in the organic layer includes the organic light-emitting material as described above.
[0119] Preferably, the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer that are sequentially stacked from the anode side to the cathode side;
[0120] Preferably, the material of the light-emitting layer includes a host material and a guest material, and the host material includes the multi-host material as described above.
[0121] Preferably, the guest material includes a phosphorescent dopant, and the phosphorescent dopant includes a complex containing a transition metal.
[0122] The present invention also provides an organic light-emitting device, which includes the organic light-emitting device as described above.
[0123] Advantages of the present invention:
[0124] 1. The organic light-emitting material provided by the present invention includes a first host material and a second host material. The first host material includes a compound represented by formula (I), and the second host material is a compound represented by formula (2). By bonding the structure of formula (II) to the main ring structure of formula (I) and cooperating with the compound represented by formula (2), and combining them as the host material of the light-emitting layer, the organic light-emitting compound can obtain high stability and a relatively balanced carrier mobility, thereby enabling the organic light-emitting device containing this material to have a more excellent lifespan, and at the same time having a lower driving voltage and higher efficiency.
[0125] 2. Further, for the organic light-emitting material provided by the present invention, the compound represented by formula (I) has any one of the structures shown in formula 1-1 to chemical formula 1-17, and cooperating with the compound represented by formula (2), and combining them as the host material of the light-emitting layer, the organic light-emitting device can have a more excellent lifespan, and at the same time have a lower driving voltage and higher efficiency. Description of the Drawings
[0126] To more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the following will briefly introduce the drawings required for the description of the specific embodiments or the prior art. Obviously, the drawings in the following description are some embodiments of the present invention. For those of ordinary skill in the art, without creative efforts, other drawings can also be obtained based on these drawings.
[0127] Figure 1 It is a structural diagram of an organic electroluminescent device in an embodiment of the device of the present invention;
[0128] Among them, 1 - substrate; 2 - anode; 3 - hole injection layer; 4 - hole transport layer; 5 - light - emitting layer; 6 - electron transport layer; 7 - electron injection layer; 8 - cathode. Specific Embodiments
[0129] The following embodiments are provided to better further understand the present invention. They are not limited to the best - mode embodiments, and do not limit the content and protection scope of the present invention. Any product that is the same as or similar to the present invention obtained by anyone under the inspiration of the present invention or by combining the features of the present invention with those of other prior arts falls within the protection scope of the present invention.
[0130] For those embodiments where specific experimental steps or conditions are not specified, the operations or conditions of the conventional experimental steps described in the literature in this field can be followed. For the reagents or instruments whose manufacturers are not specified, they are all conventional reagent products that can be obtained through commercial purchase.
[0131] Example 1
[0132] This example provides a preparation method for a compound with an N - 4 structure in an organic electroluminescent material, including the following steps:
[0133]
[0134] 1.1 Synthesis of Intermediate N - 4B’
[0135] Under nitrogen purge, add 20 g (1.0 eq) of 4a, 9.87 g (1.0 eq) of 4b, 1.7 g (2% eq) of Pd(PPh3)4, 8.37 g (2.0 eq) of NaHCO3, 180 mL of tetrahydrofuran (4a:tetrahydrofuran = 1 g:9 mL), and 60 mL of ultrapure water (4a:ultrapure water = 1 g:3 mL) to a 500 - mL three - necked flask equipped with a magnetic stirrer. React completely at 65 °C for 2 h. Purify by column chromatography to obtain 10 g of the product.
[0136] 1.2 Synthesis of Intermediate N - 4B
[0137] Add 10 g (1.0 eq) of intermediate N-4B’, 20.5 g (6.0 eq) of anhydrous FeCl3, and 100 mL of anhydrous dichloromethane (intermediate N-4B’: dichloromethane = 1 g: 10 mL) to a 250 mL three-necked flask equipped with magnetic stirring. React completely at -10 °C for 1 h. Purify by column chromatography to obtain 7 g of the product.
[0138] 1.3 Synthesis of Compound N-4
[0139] Under nitrogen purge, add 7 g (1.0 eq) of N-4B, 4.0 g (1.1 eq) of N-4A, 0.27 g (2% eq) of Pd2(dba)3, 2.85 g (2.0 eq) of t-BuONa, and 70 mL of anhydrous toluene (N-4B: anhydrous toluene = 1 g: 10 mL) to a 250 mL three-necked flask equipped with magnetic stirring. React completely at 100 °C for 2 h. Purify by column chromatography to obtain 5 g of the product (yield 53%).
[0140] Elemental analysis: C 48 H 32 Theoretical values for N2: C, 90.54; H, 5.07; N, 4.40; Measured values: C, 90.53; H, 5.08; N, 4.41; HRMS (ESI) m / z (M+): Theoretical value: 636.26; Measured value: 637.55.
[0141] Example 2
[0142] This example provides a preparation method for a compound with an N-5 structure in an organic electroluminescent material, including the following steps:
[0143]
[0144] Synthesis of Compound N-5
[0145] Under nitrogen purge, add 7 g (1.0 eq) of intermediate N-4B, 4.82 g (1.1 eq) of N-5A, 0.27 g (2% eq) of Pd2(dba)3, 2.85 g (2.0 eq) of t-BuONa, and 70 mL of anhydrous toluene to a 250 mL three-necked flask equipped with magnetic stirring. React completely at 100 °C for 2 h. Purify by column chromatography to obtain 5 g of the product (yield 49%).
[0146] Elemental analysis: C 52 H 34 Theoretical values for N2: C, 90.93; H, 4.99; N, 4.08; Measured values: C, 90.92; H, 4.98; N, 4.10; HRMS (ESI) m / z (M+): Theoretical value: 686.27; Measured value: 687.22.
[0147] Example 3
[0148] This example provides a preparation method of a compound with an N-14 structure in an organic electroluminescent material, including the following steps:
[0149]
[0150] Synthesis of Compound N-14
[0151] Under nitrogen purge, add 7 g (1.0 eq) of intermediate N-4B, 4.4 g (1.1 eq) of N-14A, 0.27 g (2% eq) of Pd2(dba)3, 2.85 g (2.0 eq) of t-BuONa, and 70 mL of anhydrous toluene into a 250 mL three-necked flask equipped with a magnetic stirrer. React completely at 100 °C for 2 h. Purify by column chromatography to obtain 5 g of the product (yield 51%).
[0152] Elemental analysis: C 50 H 32 Theoretical values for N2: C, 90.88; H, 4.88; N, 4.24; Measured values: C, 90.86; H, 4.88; N, 4.26; HRMS(ESI) m / z (M+): Theoretical value: 660.25; Measured value: 661.37.
[0153] Examples 4-16
[0154] The preparations of Examples 4-16 are similar to the above example. Specifically, the raw materials used and the products obtained in Examples 4-15 are shown in the following table:
[0155]
[0156]
[0157]
[0158] The product characterization data are as follows:
[0159]
[0160] Example 17
[0161] This example provides a preparation method of a compound with an N-423 structure in an organic electroluminescent material, including the following steps:
[0162]
[0163] Synthesis of Intermediate N-423B'
[0164] Add 20 g of 423a, 29.9 g of 423b, 2.3 g of Pd[P(C6H5)3]4, 27.9 g of K2CO3, 280 mL of toluene, 120 mL of H2O, and 120 mL of ethanol into a 1000 mL three-necked flask equipped with a mechanical stirrer, a reflux condenser, and a thermometer. Replace the gas with nitrogen three times and react at 85 °C under nitrogen protection. React for 150 min starting from the temperature rise. After the reaction is completed, add 120 mL of water to quench the reaction. After liquid separation, rotary evaporate to obtain an oily substance (wet weight 44 g), and obtain 25 g of N-423B’ after vacuum pumping.
[0165] Synthesis of Intermediate N-423B
[0166] Add the crude product of N-423B’ (oily substance) and 750 mL of dichloromethane [N-423B’: DCM = 1 g: 30 mL] into a 2 L three-necked flask equipped with a stirrer and a thermometer. Control the temperature at -5 ± 2 °C, and add ferric chloride in two batches, adding 3 equivalents of ferric chloride every 15 min, and control the temperature at -5 ± 2 °C. After the reaction is completed, slowly add 750 mL of ethanol [N-423B’: ethanol = 1 g: 30 mL], and control the temperature below 0 °C. After adding, continue to stir for 0.5 h, and yellowish-white solids will precipitate. Filter, wash the filter cake with 250 mL of ethanol [N-423B’: ethanol = 1 g: 1 mL] to obtain yellow solids. Then dissolve it with 1.75 L of chlorobenzene, desolvate and crystallize, and when it naturally drops to 60 ± 5 °C, add 250 mL of n-hexane solution dropwise and filter to obtain 20 g of crude product N-423.
[0167]
[0168] Synthesis of Compound N-423
[0169] Add 25 g of N-423A, 40.48 g of N-423B, 1.86 g of Pd2(dba)3, 1.67 g of sphos, 24.4 g of t-BuONa, and 500 mL of toluene into a 1000 mL three-necked flask equipped with a mechanical stirrer, a reflux condenser, and a thermometer. Replace the gas with nitrogen three times and react at 110 °C under nitrogen protection. React for 120 min starting from the temperature rise. After the reaction is completed, add 120 mL of water to quench the reaction. After liquid separation, rotary evaporate, pass through a column, and dry to obtain 35 g of crude product N-423 (yield 61%).
[0170] Elemental analysis: C 42 H 27 NO; Theoretical values: C, 89.81; H, 4.85; N, 2.49; O, 2.85; Measured values: C, 89.78; H, 4.86; N, 2.51; HRMS(ESI) m / z(M+): Theoretical value: 561.21; Measured value: 562.29.
[0171] Example 18
[0172] This example provides a method for preparing a compound with an N-425 structure in an organic electroluminescent material, including the following steps:
[0173]
[0174] Synthesis of Compound N-425
[0175] Add 14 g of N-425A, 18.8 g of N-423B, 0.86 g of Pd2(dba)3, 1.9 g of sphos, 9.1 g of t-BuONa, and 150 mL of toluene to a 500 mL three-necked flask equipped with a mechanical stirrer, a reflux condenser, and a thermometer. Replace the gas with nitrogen three times and react at 110 °C under nitrogen protection. React for 120 min starting from the temperature rise. After the reaction is completed, add 150 mL of water to quench the reaction. After liquid separation, spin dry, slurry with ethanol, and then desolvate and crystallize with toluene to obtain 16 g of crude N-425 (yield 55%).
[0176] Elemental analysis: C 46 H 29 Theoretical values for C, H, N, and O: C, 90.32; H, 4.78; N, 2.29; O, 2.62; Measured values: C, 90.30; H, 4.77; N, 2.32; HRMS(ESI) m / z(M+): Theoretical value: 611.22; Measured value: 612.45.
[0177] Examples 19 - 36
[0178] The preparation of Examples 19 - 36 is similar to that of Example 1. Specifically, the raw materials used in Examples 19 - 36 and the obtained products are shown in the following table:
[0179]
[0180]
[0181]
[0182]
[0183] The product characterization data are as follows:
[0184]
[0185]
[0186] Example 37
[0187] This embodiment provides a method for preparing a compound with an N-912 structure in an organic electroluminescent material, comprising the following steps:
[0188]
[0189] A mixture of 35.2 g (100 mmol) of 2,7-dibromo-9,9-dimethyl-9H-fluorene, 21.8 g (110 mmol) of 2-biphenylylboronic acid, 2.31 g (2 mmol) of Pd(PPh3)4, 75 ml of 2M Na2CO3, 150 ml of EtOH, and 300 ml of toluene was degassed and placed under nitrogen, and then heated at 100 °C for 12 hours. After completion of the reaction, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate and water, dried over anhydrous magnesium sulfate, the solvent was removed, and the residue was purified by column chromatography on a silica gel-packed column to give the product as a white solid (26.8 g, 63.0 mmol, 63%).
[0190] In a 3000 ml three-necked flask that was degassed and filled with nitrogen, 26.8 g (60 mmol) of 2-(biphenyl-2-yl)-7-bromo-9,9-dimethyl-9H-fluorene was dissolved in anhydrous dichloromethane (1500 ml), then 97.5 g (600 mmol) of iron(III) chloride was added and the mixture was stirred for one hour. 500 ml of methanol was added to the mixture, and the organic layer was separated and the solvent was removed in vacuo. The residue was purified by column chromatography (hexane-dichloromethane) on a silica gel-packed column to give a white solid (the final structure as shown above) (10.7 g, 25.3 mmol, 40%).
[0191]
[0192] A mixture of 20 g (41.3 mmol) of N-(biphenyl-4-yl)-9,9'-spirobifluorene-2-amine, 14 g (49.5 mmol) of 1-bromo-4-iodobenzene, 2.4 g (12.4 mmol) of copper(I) iodide, 17.1 g (123.9 mmol) of potassium carbonate, and 300 ml of DMF was refluxed overnight under nitrogen. After completion of the reaction, it was then cooled to room temperature. The organic layer was extracted with ethyl acetate and water, dried over anhydrous magnesium sulfate, the solvent was removed, and the residue was purified by column chromatography (hexane-dichloromethane) on a silica gel-packed column to give 26.3 g (yield 43%) of the product as a white solid.
[0193] A mixture of 10 g (15.6 mmol) of N-(biphenyl-4-yl)-N-(4-bromophenyl)-9,9'-spirobi[fluorene]-2-amine, 4.75 g (18.72 mmol) of bis(pinacolato)diboron, 0.18 g (0.156 mmol) of tetrakis(triphenylphosphine)palladium, 2 g (20.28 mmol) of potassium acetate, and 300 ml of 1,4-dioxane was degassed and placed under nitrogen, and then heated at 90 °C for 16 h. After completion of the reaction, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate and water, dried over anhydrous magnesium sulfate, the solvent was removed, and the product was purified by column using a mixture of hexane and ethyl as the eluent to obtain 8.77 g of a pale yellow product (yield 82%).
[0194]
[0195] A mixture of 15 g (35.43 mmol) of 12-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphenylene, 29.1 g (42.51 mmol) of N-(biphenyl-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9,9'-spirobifluorene-2-amine, 0.41 g (0.35 mmol) of tetrakis(triphenylphosphine)palladium, 23 ml of 2M Na2CO3, 100 ml of EtOH, and 200 ml of toluene was degassed and placed under nitrogen, and then heated at 100 °C for 8 hours. After completion of the reaction, the mixture was cooled to room temperature. The organic layer was extracted with dichloromethane and water, dried over anhydrous magnesium sulfate, the solvent was removed, and the residue was purified by column chromatography (hexane-dichloromethane) packed with silica gel to obtain 17.5 g (yield 55%) of the product as a yellow solid.
[0196] Elemental analysis: C 70 H 47 Theoretical values: C, 93.20; H, 5.25; N, 1.55; Found: C, 93.16; H, 5.27; N, 1.57; HRMS (ESI) m / z (M+): Theoretical value: 901.37; Found: 902.21.
[0197] Example 38
[0198] This example provides a method for preparing a compound having an N-895 structure in an organic electroluminescent material, comprising the following steps:
[0199]
[0200] A mixture of 5 g (11.8 mmol) of 12-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphenylene, 6.8 g (14.1 mmol) of N-(biphenyl-4-yl)-9,9'-spirobifluorene-2-amine, 0.03 g (0.11 mmol) of palladium(II) acetate, 0.04 g (0.11 mmol) of 2-(dicyclohexylphosphino)biphenyl, 1.7 g (17.7 mmol) of sodium tert-butoxide and 100 ml of toluene was refluxed overnight under nitrogen. After completion of the reaction, it was then cooled to room temperature. The organic layer was extracted with dichloromethane and water, dried over anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography (hexane-dichloromethane) packed with silica gel to give 5.8 g (yield 60%) of the product as a yellow solid.
[0201] Elemental analysis: C 64 H 43 Theoretical values for C, H, N: C, 93.06; H, 5.25; N, 1.70; Found: C, 93.02; H, 5.25; N, 1.73; HRMS (ESI) m / z (M+): Theoretical value: 825.34; Found: 826.19.
[0202] Examples 39 - 45
[0203] The preparations of Examples 39 - 45 were similar to the above example. Specifically, the starting materials used in Examples 38 - 41 and the products obtained are shown in the following table:
[0204]
[0205]
[0206] The product characterization data are shown below:
[0207]
[0208]
[0209] Example 46
[0210] This example provides a method for preparing a compound having the M-17 structure in an organic electroluminescent material, comprising the following steps:
[0211]
[0212] Synthesis of M-17: Take a 50 mL two-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux tube above. After drying, fill it with nitrogen. Respectively add compound M17-A (14.1 mmol), M17-B (18.3 mmol), tetrakis(triphenylphosphine)palladium (0.7 mmol), potassium carbonate (28.2 mmol), 42 mL of toluene, 10 mL of ethanol and 14 mL of distilled water, and stir the mixture at 140 °C for 8 hours. After the reaction is completed, add the mixture dropwise to methanol, and filter the obtained solid. Purify the obtained solid by column chromatography to obtain compound M-17 (5.8 g, yield: 75%).
[0213] Elemental analysis: C 39 H 23 For C, H, N3O theoretical values: C, 85.23; H, 4.22; N, 7.65; O, 2.91; measured values: C, 85.22; H, 4.21; N, 7.66; HRMS(ESI) m / z (M+): theoretical value: 549.18; measured value: 550.57.
[0214] Example 47
[0215] This example provides a preparation method of a compound with M-230 structure in an organic electroluminescent material, including the following steps:
[0216]
[0217] Synthesis of intermediate M230-A
[0218] Add intermediate M230-1 (20 g) to a 250 mL three-necked flask equipped with a thermometer and magnetic stirring, and 200 mL of anhydrous tetrahydrofuran. Under nitrogen protection, cool the temperature to -78 °C, control the temperature and dropwise add n-butyllithium (1.6 M 45.2 mL). After the addition, stir for 1 h, then control the temperature at -78 °C and dropwise add triisopropyl borate (19.52 g). After the addition, transfer it to room temperature and react for 12 h. Dropwise add hydrochloric acid solution (6.5 mL of 36% concentrated hydrochloric acid + 24 mL of water). Add 50 mL of ethyl acetate and 25 mL of water to the reaction solution for extraction and liquid separation. Rotate and dry the organic phase, add 50 mL of n-hexane, reflux and stir for 1 h, filter at room temperature, and obtain intermediate M230-2, 15 g after drying.
[0219] Add intermediate M230-2 (15 g), intermediate 3-bromopyridine-4-carbaldehyde (11.2 g), potassium carbonate (16.6 g) and tetrakis(triphenylphosphine)palladium(0) (2.0 g) to a 250 mL three-necked flask equipped with a thermometer and magnetic stirring. Add toluene (80 mL), ethanol (35 mL) and water (35 mL). Under nitrogen protection, heat to 85 °C and react for 6 h. Add 50 mL of ethyl acetate and 25 mL of water to the reaction solution for extraction and liquid separation. The organic phase is stirred and passed through a column to obtain intermediate M230-3, 15.2 g.
[0220] Add intermediate M230-3 (15.2 g) and (methoxymethyl)triphenylphosphonium chloride (23.5 g) to a 250 mL three-necked flask equipped with a thermometer and magnetic stirring. Add 75 mL of anhydrous tetrahydrofuran. Under nitrogen protection, control the temperature to -5 °C and dropwise add a tetrahydrofuran solution of potassium tert-butoxide (10.2 g, 76 mL). After dropping, react for 1 h. Add 50 mL of ethyl acetate and 25 mL of water to the reaction solution for extraction and liquid separation. The organic phase is stirred and passed through a column to obtain intermediate M230-4, 14 g.
[0221] Add intermediate M230-4 (14 g) and 1,1,1,3,3,3-hexafluoroisopropanol (70 mL) to a 250 mL three-necked flask equipped with a thermometer and magnetic stirring. Under nitrogen protection, control the temperature to 0 °C and dropwise add trifluoromethanesulfonic acid (11 mL). After dropping, react for 1 h. Add 30 mL of dichloromethane and 25 mL of water to the reaction solution for extraction and liquid separation. The organic phase is stirred and passed through a column to obtain intermediate M230-5, 5 g.
[0222] Add intermediate M230-5 (5 g), bis(pinacolato)diboron (5 g), potassium acetate (4 g) and Pd(dppf)Cl2 (0.25 g) to a 250 mL three-necked flask equipped with a thermometer and magnetic stirring. Add 1,4-dioxane (60 mL). Under nitrogen protection, heat to 110 °C and react for 4 h. Add 60 mL of ethyl acetate and 100 mL of water to the reaction solution for extraction and liquid separation. The organic phase is stirred and passed through a column to obtain intermediate M230-A 5 g.
[0223] Synthesis of Compound M-230
[0224]
[0225] Add intermediate M230-A (5 g), intermediate M230-B (4.5 g), potassium carbonate (4.5 g) and tetrakis(triphenylphosphine)palladium(0) (0.54 g) to a 250 mL three-necked flask equipped with a thermometer and magnetic stirring. Add toluene (50 mL), ethanol (20 mL) and water (20 mL). Under nitrogen protection, heat to 85 °C and react for 6 h. Add water and ethanol to the reaction solution at room temperature for filtration. After drying, product M230, 5 g (yield 50%) is obtained.
[0226] Elemental analysis: C 38H 24 Theoretical values of N4: C, 85.05; H, 4.51; N, 10.44; Measured values: C, 83.45; H, 4.39; N, 12.16; HRMS(ESI) m / z (M+): Theoretical value: 536.20; Measured value: 537.09.
[0227] Examples 48 - 54
[0228] The preparation of Examples 48 - 54 is similar to the above examples. Specifically, the raw materials used in Examples 48 - 54 and the obtained products are shown in the following table:
[0229]
[0230]
[0231] The product characterization data are as follows:
[0232]
[0233] Device Example
[0234] This example provides an organic electroluminescent device, as Figure 1 shown, including an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8 that are sequentially stacked on a substrate 1. Its device structure is: anode (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / light-emitting layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Al).
[0235] The materials for manufacturing the organic electroluminescent device are as follows:
[0236]
[0237] The preparation of the above organic electroluminescent device includes the following steps:
[0238] 1) Substrate cleaning:
[0239] The glass substrate coated with transparent ITO is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤ 10 wt%, triethanolamine ≤ 1 wt%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (the volume ratio of acetone to ethanol is 1:1), baked in a clean environment until all moisture is removed, and then cleaned with ultraviolet light and ozone.
[0240] 2) Organic layer preparation:
[0241] Transfer the ITO transparent substrate into the evaporation equipment and evacuate it to 1×10 -6 to 2×10 -4 Pa, and then deposit a 10-nm hole injection layer (HIL) / 80-nm hole transport layer (HTL) / 38-nm emitting layer (EML) / 30-nm electron transport layer (ETL) / 1-nm electron injection layer (EIL) / 80-nm-thick cathode (Al) on the anode film in sequence.
[0242] Among them:
[0243] The material of the hole injection layer (HIL) is a mixture of NDP-9 and HT, and the mass ratio of NDP-9 to HT is 3:97;
[0244] The material of the hole transport layer (HTL) is HT;
[0245] The material of the emitting layer (EML) includes a host material and a guest material. The host material is the compound represented by formula (I) and the compound represented by formula (2) prepared in the present invention, and the guest material is (piq)2Ir(acac); the specific materials and ratios are shown in Table 1;
[0246] The material of the electron transport layer (ETL) is shown in Table 1;
[0247] The material of the electron injection layer (EIL) is LiQ;
[0248] The cathode is aluminum;
[0249] Some layers of the organic light-emitting device, their materials and thicknesses are shown in Table 1.
[0250] Table 1
[0251]
[0252]
[0253]
[0254] Test Example
[0255] Test the organic light-emitting devices obtained from Device Examples 1-18 and Device Comparative Examples 1-22 in the device examples.
[0256] Instrument: The current, voltage, brightness, emission spectrum and other characteristics of the device are synchronously tested using a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system;
[0257] Test conditions: The optoelectronic characteristic test condition: the current density is 10 mA / cm2.
[0258] Lifetime test: When the current density is 50 mA / cm2, record the time (in hours) when the device brightness drops to 95% of the original brightness.
[0259] The test results of the device performance are shown in Table 2:
[0260] Table 2
[0261]
[0262]
[0263] As can be seen from Table 2, the compound N provided by the present invention cooperates with the compound M and has a synergistic effect. Using it as the host material of the light-emitting layer can effectively reduce the interlayer energy level difference, balance the electron and hole transport rates, effectively improve the lifetime of the organic light-emitting diode, and at the same time enable the device to have a lower driving voltage and a higher current efficiency.
[0264] Obviously, the above embodiments are merely examples for clear illustration and are not limitations on the implementation manners. For those of ordinary skill in the art, other different forms of changes or modifications can be made based on the above description. It is not necessary and impossible to enumerate all the implementation manners here. And the obvious changes or modifications derived therefrom are still within the protection scope of the present invention.
Claims
1. An organic electroluminescent material, characterized in that, The organic electroluminescent material comprises a first host material and a second host material, and the first host material comprises a compound represented by formula (I): Among them, X is selected from O, S, Se, NAr, CR 6 R 7 ; R 1 is —L 1 Ar 1 ,R 2 is —L 2 Ar 2 ,R 3 is —L 3 Ar 3 ; Ar is selected from hydrogen, deuterium, C6-C30 aryl; R 6 ,R 7 each independently selected from a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, L 1 -L 3 Each independently selected from a linking group, a C6-C30 arylene group; Ar 1 -Ar 3 At least one of them is a structure represented by formula (II), and the others are hydrogen, deuterium, or tritium; R 4 is —L 4 Ar 4 ,R 5 is —L 5 Ar 5 , Among them, L 4 -L 5 are each independently selected from a linking group, an arylene group having 6 to 30 carbon atoms; Ar 4 -Ar 5 Each is independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; The second host material is a compound represented by formula (2): Wherein, X 1 and X 2 are each independently selected from N or CR, and R is selected from hydrogen or deuterium; L is selected from a linking bond; Ar 8 ,Ar 9 each independently selected from substituted or unsubstituted C6-C30 aryl, C3-C30 heteroaryl; The substituents in the substituted C6-C30 aryl and the substituted C3-30 heteroaryl are selected from one or a combination of two of deuterium, C1-C6 alkyl, C6-C30 aryl, and C3-C30 heteroaryl; In the organic electroluminescent material, the mass ratio of the compound represented by formula (1) to the compound represented by formula (2) is 4:6 - 6:
4.
2. The organic electroluminescent material according to claim 1, characterized in that, In the second host material, L is a linking bond; Ar 8 , Ar 9 are each independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, group, dimethylfluorene group, spirobifluorene group, fluoranthenyl group, diphenylfluorene group, benzyldimethylfluorene group, benzylbiphenylfluorene group, benzospirobifluorene group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, phenylcarbazolyl group, dipyridyl group, pyrimidinyl group, triazinyl group.
3. The organic electroluminescent material according to claim 2, wherein In the second main material, X 1 , X 2 are each independently selected from CR, and R is selected from hydrogen or deuterium; Or, X 1 Selected from N, X 2 Selected from CR, where R is selected from hydrogen or deuterium.
4. The organic electroluminescent material according to claim 3, wherein The compound represented by formula (2) has any one of the following structures:
5. The organic electroluminescent material according to claim 1, wherein In the first host material, L 1 -L 3 is selected from a linking bond, a C6-C30 arylene group; Ar 1 -Ar 3 One of them is a structure represented by formula (II), and the remaining two are selected from hydrogen.
6. The organic electroluminescent material according to claim 1, characterized in that, L 1 -L 3 selected from a linking group, an arylene group having 6 to 30 carbon atoms, Ar 1 -Ar 3 Two of them are the structures shown in formula (II), and the remaining one is selected from hydrogen.
7. The organic electroluminescent material according to claim 5, characterized in that, In the first host material, Ar is selected from C6-C30 aryl; R 6 ,R 7 each independently selected from C1-C5 alkyl; Ar 4 -Ar 5 Each independently selected from C6-C30 aryl, C3-C30 heteroaryl.
8. The organic electroluminescent material according to claim 1, wherein Ar is selected from phenyl, naphthyl, biphenyl, terphenyl, triphenylene, yl, dibenzofuranyl, dibenzothiophenyl.
9. The organic electroluminescent material according to claim 1, characterized in that, L 4 -L 5 Each is independently selected from a linking group, a phenylene group, and a naphthylene group.
10. The organic electroluminescent material according to claim 1, characterized in that, L 4 -L 5 Each is independently selected from linking keys.
11. The organic electroluminescent material according to claim 1, wherein Ar 4 -Ar 5 Each independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, group, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, triphenylene, dimethylfluorenyl, spirobifluorenyl, fluoranthenyl, carbazolyl, phenylcarbazolyl, diphenylfluorenyl, benzyldimethylfluorenyl, benzyl diphenylfluorenyl, benzospirobifluorenyl, pyridyl, pyrimidinyl, triazinyl.
12. The organic electroluminescent material according to claim 1, wherein Ar 4 、Ar 5 Each independently is selected from the structures represented by the following formula (III) or formula (IV): R T1 -R T6 Each independently selected from hydrogen, deuterium, C1-C30 alkyl, C6-C30 aryl, C3-C30 heteroaryl; or, R T1 -R T5 adjacent ones of which are fused to each other to form ring A, and the ring A is selected from phenyl, naphthyl, phenanthryl; When there are multiple Rs T1 -R T6 At this time, the Rs T1 -R T6 are each independent of one another and can be the same or different; Y is selected from O, S, NAr, CR 6 R 7 ; Wherein the definitions of Ar, R6, and R7 are the same as those in claim 1.
13. The organic electroluminescent material according to claim 1, wherein In the first host material, the compound represented by formula (I) has any one of the structures shown in Chemical Formula 1-1 to Chemical Formula 1-17: wherein R 1 -R 7 、L 1 -L 3 、Ar are as defined in claim 1.
14. The organic electroluminescent material according to claim 13, characterized in that, R 1 -R 3 Each independently selected from hydrogen; R 6 、R 7 Each independently selected from C1-C5 alkyl; R 4 is —L 4 Ar 4 wherein R 5 is —L 5 Ar 5 and L 4 -L 5 are each independently selected from a linking group, an arylene group having 6 to 30 carbon atoms.
15. The organic electroluminescent material according to claim 13, wherein R 6 、R 7 Each independently selected from methyl and ethyl.
16. The organic electroluminescent material according to claim 13, wherein L 4 -L 5 Each independently selected from a linking group, a phenylene group, and a naphthylene group.
17. The organic electroluminescent material according to claim 13, characterized in that, L 4 -L 5 Each is independently selected from linking keys; Ar 4 -Ar 5 Each is independently selected from C6-C30 aryl and C3-C30 heteroaryl.
18. The organic electroluminescent material according to claim 13, wherein Ar 4 -Ar 5 Each independently selected from the following groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, group, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, triphenylene, dimethylfluorenyl, spirobifluorenyl, fluoranthenyl, carbazolyl, phenylcarbazolyl, diphenylfluorenyl, benzyldimethylfluorenyl, benzyl diphenylfluorenyl, benzospirobifluorenyl, pyridyl, pyrimidinyl, triazinyl.
19. The organic electroluminescent material according to claim 13, wherein L 1 -L 3 Each is independently selected from a linking group and an arylene group having 6 to 30 carbon atoms.
20. The organic electroluminescent material according to claim 13, characterized in that, L 1 -L 3 Each is independently selected from a linking group, a phenylene group, a naphthylene group, a triphenylene group, and a biphenylene group.
21. The organic electroluminescent material according to claim 13, wherein L 1 selected from linking keys, L 2 selected from phenylene, naphthylene, terphenylenylene, biphenylenylene, L 3 is a linking key; Ar is selected from C6-C30 aryl; The C6-C30 aryl is selected from phenyl, naphthyl, and biphenyl.
22. The organic electroluminescent material according to claim 1, wherein In the first host material, the compound represented by formula (I) has any one of the following structures:
23. Use of the organic electroluminescent material according to any one of claims 1-22 in the preparation of an optical device.
24. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises an anode and a cathode, and an organic layer disposed between the anode and the cathode, and the organic layer comprises the organic electroluminescent material according to any one of claims 1-22.
25. The organic electroluminescent device according to claim 24, wherein The light-emitting layer in the organic layer comprises the organic electroluminescent material according to any one of claims 1-22.
26. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises the organic electroluminescent device according to claim 24.
Citation Information
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