Chain silicon compound and application thereof
By using chain silicon compounds as key layer materials for organic electroluminescent elements, the shortcomings of existing materials in carrier injection and transport performance, electroluminescent performance and lifespan are solved, the driving voltage is reduced, the luminous efficiency is improved and the element life is extended, and the performance of full-color organic light-emitting panels is optimized.
Patent Information
- Application Number
- CN202510686808.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-05-26
- Publication Date
- 2025-09-23
AI Technical Summary
Existing organic electroluminescent materials have deficiencies in carrier injection and transport performance, material electroluminescent properties, service life and color purity, which affect the performance and life of OLED components.
Chain silicon compounds are used as hole injection layer, hole transport layer, light-emitting layer, electron transport layer or hole blocking layer materials of organic electroluminescent elements. By introducing multiple substituents to adjust the HOMO and LUMO energy levels, the electron transport capacity and thermal stability are improved.
Significantly reduce driving voltage, improve luminous efficiency and life, enhance triplet-triplet fusion effect, and optimize the performance of full-color organic light-emitting panels.
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Figure CN120682267A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to the technical field of organic electroluminescent materials, and in particular to a chain silicon compound and its application in organic light-emitting elements. Background Art
[0002] In recent years, organic electroluminescent display (OLED) technology has matured, and some products have entered the market. However, many challenges remain to be addressed during industrialization. In particular, many issues remain to be resolved regarding the various organic materials used to make the components, including their carrier injection and transport properties, electroluminescent properties, service life, color purity, and matching between the various materials and with the electrodes. OLEDs utilize organic thin films that emit light when a voltage is applied to the device. OLEDs are becoming an increasingly popular technology for applications such as displays, lighting, and backlighting.
[0003] Therefore, in order to overcome the above-mentioned technical problems and further improve the characteristics of organic electroluminescent elements, there is a continuous demand for the development of more stable and effective substances that can be used as electron injection and transport substances in organic electroluminescent elements.
[0004] In view of this, the present invention is proposed. Summary of the Invention
[0005] The present invention aims to provide a chain silicon compound that can improve the thermal stability of the material and the ability to transport carriers. An organic electroluminescent element prepared using the chain silicon compound can significantly reduce the driving voltage and improve the luminous efficiency and lifespan. Another object of the present invention is to provide an application of the compound.
[0006] Specifically, the present invention provides the following technical solutions:
[0007] The present invention provides a chain silicon compound, the structural formula of which is shown in formula (I):
[0008]
[0009] in,
[0010] L 1 Selected from substituted or unsubstituted C6-C 60 Arylene, substituted or unsubstituted C2-C 60 A group consisting of a heteroarylene group, or an amino group;
[0011] L 2 Each independently selected from a single bond, a substituted or unsubstituted C6-C 60 Arylene, or substituted or unsubstituted C2-C 60 The group consisting of heteroarylene;
[0012] n represents an integer from 1 to 5, such as 2, 3 or 4;
[0013] m represents an integer from 0 to 5, such as 1, 2, 3 or 4;
[0014] Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Each independently selected from substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Arylamine, or substituted or unsubstituted C2-C 60 The group consisting of heteroaryl groups;
[0015] Het represents a substituted or unsubstituted C2-C 60 Heteroaryl, substituted or unsubstituted C6-C 60 aryl;
[0016] Optionally, L 1 、L 2 、Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 The substituents substituted in Het are each independently selected from hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, amidine, hydrazine, hydrazone, carboxyl or its carboxylate, sulfonic acid or its sulfonate, phosphate or its phosphate, C1-C 40 Alkyl, C2-C 40 Alkenyl, C2-C 40 Alkynyl, C1-C 40 Alkoxy, C3-C 40 Cycloalkyl, C3-C 40 Cycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Aryl sulfide group and C2-C 60 Any one or a combination of at least two of the heterocyclic aromatic groups.
[0017] The chain silicon compound according to the present invention is represented by the above chemical formula (I), wherein the chain silicon compound comprises two tetravalent silicon derivatives connected by a single bond, an arylene group, or a heteroarylene group. 1 、L 2Combined with a heteroaryl group to form a basic skeleton. The compound represented by formula (I) of the present invention is not only electrochemically stable and has excellent electron mobility, but also has a high glass transition temperature and excellent thermal stability compared to the single tetravalent silicon substituents known in the past. Thus, the chain silicon compound of the present invention has excellent electron transport ability and luminescent properties, and can therefore be used as a material for any one of the hole injection layer, hole transport layer, light-emitting layer, electron transport layer and hole blocking layer of the organic layer of an organic electroluminescent element. It is preferably a material for any one of the light-emitting layer, the electron transport layer and the electron transport auxiliary layer stacked in one step on the electron transport layer, and more preferably a material for the electron transport layer, the electron transport auxiliary layer and the light-emitting layer.
[0018] Specifically, the compound shown in the compound formula (I) of the present invention passes through the heterocyclic compound comprising two tetravalent silicon derivatives, so as to have a stronger electron transport ability compared with the heterocycle of a tetravalent silicon derivative, it is possible to show relatively high luminous efficiency and high glass transition temperature. Thus, in the case where the compound shown in the formula (I) of the present invention is used for an organic electroluminescent element, it is possible not only to have excellent thermal stability, carrier transport ability, electron transport ability and luminous ability, but also to reduce the driving voltage of the element, improve efficiency and lifespan, and as the latest electron transport layer material, it is possible to show the excellent efficiency caused by the triplet-triplet fusion effect due to high triplet energy level.
[0019] Furthermore, the chain silicon compound represented by formula (I) of the present invention is modified by introducing various substituents Ar into the basic skeleton. 1 、Ar 2 、Ar 3 、Ar 4 and Ar 5 The HOMO and LUMO energy levels can be adjusted according to the type of substituent, thereby having a wide band gap. An organic electroluminescent device using such a compound can exhibit high electron transport properties.
[0020] In addition, the heterocyclic compound represented by formula (I) of the present invention is modified by introducing various substituents L into the above basic skeleton. 1 、L 2 and Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5, especially aryl and / or heteroaryl groups, significantly increases the molecular weight of the compound, thereby raising the glass transition temperature and thus having higher thermal stability than previous luminescent materials, such as phenanthridine. Therefore, the performance and lifespan characteristics of organic electroluminescent devices containing the compounds according to the present invention can be greatly improved. Organic electroluminescent devices with such improved performance and lifespan characteristics can ultimately maximize the performance of full-color organic light-emitting panels.
[0021] An aryl group, as defined herein, contains 6 to 60 carbon atoms, and a heteroaryl group contains 2 to 60 carbon atoms and at least one heteroatom, provided that the total number of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O, or S. In this case, the two or more rings of the heteroaryl group may be simply attached to each other or attached in a condensed form, and further, may also be condensed with the aryl group. Non-limiting examples of such heteroaryl groups include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathiyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazolyl, and carbazolyl; and 2-furyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, and 2-pyrimidinyl.
[0022] Furthermore, the aryl, heteroaryl or heterocyclic aryl is preferably selected from phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, pyrenyl, yl, peryl, fluoranthenyl, tetraphenyl, pentacene, benzopyrenyl, biphenyl, phenylene, terphenyl, triphenyl, quadriphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, triphenylene, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, cis- or trans-indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzocarbazolyl, dibenzocarbazolyl, azadibenzo[g,ij]naphtho[2,1,8-cde]azulene, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, spiroistrimerized indenyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo[5,6]quinolyl, benzo[6,7]quinolyl, benzo[7,8]quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, isoxazolyl, 1,2- Thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazatriphenylenyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorescein ring group, naphthyridinyl, azacarbazolyl, benzocarbolinyl, carbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1 ,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl or a group derived from a combination of these systems.
[0023] In some embodiments, Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Each independently selected from substituted or unsubstituted C6-C 30 (e.g. C6, C9, C 10 、C 12 、C 14、C 15 、C 16 、C 18 、C 20 、C 22 、C 24 、C 26 、C 28 etc.) aryl, substituted or unsubstituted C2-C 30 (e.g. C4, C6, C9, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 、C 20 、C 22 、C 24 、C 26 、C 28 etc.) heteroaryl groups.
[0024] In some embodiments, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 are each independently selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, pyrenyl, phenyl, fluorenyl, peryl, fluoranthenyl, tetraphenyl, pentacene, benzopyrenyl, biphenyl, phenylene, terphenyl, triphenyl, quadriphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, triphenylene, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, cis- or trans-indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzocarbazolyl, dibenzocarbazolyl, azadibenzo[g,ij]naphtho[2,1,8-cde]azulene, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, spiroistrimerized indenyl, furanyl, benzofuranyl, isobenzofuran yl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo[5,6]quinolyl, benzo[6,7]quinolyl, benzo[7,8]quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, isoxazolyl, 1 ,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazatriphenylene radical, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorescein ring radical, naphthyridinyl, azacarbazolyl, benzocarbolinyl, carbolinyl, phenanthroline radical, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazole oxazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl or a group derived from a combination of these systems.
[0025] In some embodiments, Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted pyridyl.
[0026] In some embodiments, the Ar1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 The substituents substituted in the substituted are independently selected from deuterium, halogen (F, Cl, Br or I), cyano, C1-C 10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C 10 (e.g. C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C 20 (e.g., C7, C8, C9, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 etc.) aryl, C3-C 20 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 any one or a combination of at least two of the heteroaryl groups (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62
[0027] In some embodiments, each Het is independently selected from substituted or unsubstituted C2-C 30 (e.g. C4, C6, C9, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 、C 20 、C 22 、C 24 、C 26 、C 28 etc.) heteroaryl, substituted or unsubstituted C6-C 30 (e.g. C6, C9, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 、C 20 、C 22 、C 24 、C26 、C 28 etc.) aromatic groups.
[0028] In some embodiments, the Het is selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, pyrenyl, phenyl, benzothiophene, benzopyrenyl, biphenyl, phenylene, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, triphenylene, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo[5 ,6]quinolyl, benzo[6,7]quinolyl, benzo[7,8]quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, isoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazatriphenylenyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoline Oxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorescein ring group, naphthyridinyl, azacarbazolyl, benzocarbolinyl, carbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl or a group derived from a combination of these systems.
[0029] In some embodiments, the substituents substituted in Het are independently selected from deuterium, halogen (F, Cl, Br or I), cyano, C1-C 10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C 10 (e.g. C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C20 (e.g. C7, C8, C9, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 etc.) aryl, C3-C 20 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 any one or a combination of at least two of the heteroaryl groups.
[0030] According to an embodiment of the present invention, the Het is selected from the group consisting of the following groups shown in II-1 to II-13:
[0031]
[0032] in,
[0033] Z1 and Z2 are each independently selected from hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, amidine, hydrazine, hydrazone, carboxyl or its carboxylate, sulfonic acid or its sulfonate, phosphate or its phosphate, C1-C 40 Alkyl, C2-C 40 Alkenyl, C2-C 40 Alkynyl, C1-C 40 Alkoxy, C3-C 40 Cycloalkane, C3-C 40 Cycloalkene, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Aryl sulfide, substituted or unsubstituted C6-C 60 Arylamine, or substituted or unsubstituted C2-C 60 A group consisting of heteroaryl groups; adjacent Z1s are not connected or are connected to form a ring through chemical bonds, and adjacent Z2s are not connected or are connected to form a ring through chemical bonds
[0034] x1 represents an integer from 1 to 4, such as 2 or 3; x2 represents an integer from 1 to 3, such as 2; x3 represents 1 or 2; x4 represents an integer from 1 to 6, such as 2, 3, 4 or 5; x5 represents an integer from 1 to 5, such as 2, 3 or 4;
[0035] T1 and T2 represent O, S, CR'R" or NAr';
[0036] R', R" are each independently selected from hydrogen, C1-C 60 Alkyl, C1-C 60 Heteroalkyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Arylamine, or substituted or unsubstituted C2-C 60 A group consisting of heteroaryl groups, R' and R" may be optionally joined or fused to form one or more additional substituted or unsubstituted rings, containing or not containing one or more heteroatoms N, P, B, O or S in the formed rings; preferably, R', R" are hydrogen, methyl, phenyl or fluorenyl;
[0037] Ar' is selected from C1~C 40 Alkyl, C1~C 40 Heteroalkyl, C3~C 40 Cycloalkyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C 10 -C 60 Condensed ring aromatic group, substituted or unsubstituted C6-C 60 Arylamine, or substituted or unsubstituted C2-C 60 The group consisting of heteroaryl; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
[0038] represents the attachment site of the group;
[0039] Optionally, the substituents substituted in Z1, Z2, R', R", and Ar' are independently selected from deuterium, halogen (F, Cl, Br or I), cyano, C1-C 10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C 10 (e.g. C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C 20 (e.g. C7, C8, C9, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 etc.) aryl, C3-C 20 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 any one or a combination of at least two of the heteroaryl groups.
[0040] In some embodiments, Z1 and Z2 are each independently selected from hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, or substituted or unsubstituted groups:
[0041]
[0042] T is selected from O, S, Se, CMe2, CPh2, CFlu, NPh, NPhPh, Me represents a methyl group, Ph represents a phenyl group, PhPh represents a biphenyl group, and Flu represents a fluorenyl group;
[0043] Preferably, the substituents in Z1 and Z2 are selected from any one of deuterium, halogen, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, sec-butyl, tert-butyl, deuterated tert-butyl, isobutyl, isopentyl, tert-pentyl, cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, naphthyl, pyridyl, and carbazolyl.
[0044] In some embodiments, NPhPh is selected from In some embodiments, CFlu is selected from
[0045] In some embodiments, adjacent Z1s are not connected or are connected by chemical bonds to form the following ring; adjacent Z2s are not connected or are connected by chemical bonds to form the following ring: C3-C 10 (e.g. C4, C5, C6, C7, C8, C9, etc.) alicyclic, substituted or unsubstituted C3-C 20 (e.g. C3, C4, C5, C6, C9, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 etc.) heteroaromatic ring or substituted or unsubstituted C6-C 20 (e.g. C6, C9, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 etc.) aromatic rings.
[0046] Preferably, adjacent Z1s are not connected or are connected by chemical bonds to form the following ring, and adjacent Z2s are not connected or are connected by chemical bonds to form the following ring:
[0047] etc., the dotted line represents a fused bond). wherein the ring is optionally selected from deuterium, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C6-C 12 Aryl, C3-C 12The heteroaryl group is substituted by any one or more substituents.
[0048] In the chain silicon compound represented by formula (I) of the present invention, L 1 、L 2 The functional group for connecting the two tetravalent silicon derivatives to Het can be selected from single bonds, C6-C 60 Arylene and C2-C 60 In this case, preferably, the L 1 、L 2 Each independently selected from any one of the following formulas (20) to (35):
[0049]
[0050]
[0051] wherein Y is selected from O, S, SO, SO2, Se, CR'R", SiR'R" or NAr';
[0052] R represents one, two or more to saturated substitution, and each is independently selected from hydrogen, deuterium, halogen atoms, hydroxyl, nitrile, nitro, amino, amidine, hydrazine, hydrazone, carboxyl or its carboxylate, sulfonic acid or its sulfonate, phosphoric acid or its phosphate, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Cycloalkane, C3-C 60 Cycloalkene, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Aryl sulfide group, or substituted or unsubstituted C2-C 60 The group consisting of heteroaryl groups;
[0053] R', R" are each independently selected from hydrogen, C1-C 60 Alkyl, C1-C 60 Heteroalkyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Arylamine, or substituted or unsubstituted C2-C 60 A group consisting of heteroaryl groups, R' and R" may be optionally joined or fused to form one or more additional substituted or unsubstituted rings, containing or not containing one or more heteroatoms N, P, B, O or S in the formed rings; preferably, R', R" are hydrogen, methyl, phenyl or fluorenyl;
[0054] Ar' is selected from C1-C 60 Alkyl, C1-C 60 Heteroalkyl, C3-C 60 Cycloalkyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Condensed ring aromatic group, substituted or unsubstituted C6-C 60 Arylamine, or substituted or unsubstituted C2-C 60 The group consisting of heterocyclic aromatic groups; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
[0055] Dashed lines represent the attachment sites of the groups;
[0056] Optionally, the substituents substituted in R, R', R", Ar' are independently selected from deuterium, halogen (F, Cl, Br or I), cyano, C1-C 10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C 10 (e.g. C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C 20 (e.g. C7, C8, C9, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 etc.) aryl, C3-C 20 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 any one or a combination of at least two of the heteroaryl groups.
[0057] In some embodiments, R is selected from hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, or a substituted or unsubstituted group:
[0058]
[0059] Preferably, the substituent in R is selected from deuterium, halogen, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, sec-butyl, tert-butyl, deuterated tert-butyl, isobutyl, isopentyl, tert-pentyl, cyclopentyl, cyclohexyl, phenyl or one or a combination of at least two of the following groups:
[0060]
[0061] T is selected from O, S, Se, CMe2, CPh2, CFlu, NPh, NPhPh, Me represents a methyl group, Ph represents a phenyl group, PhPh represents a biphenyl group, and Flu represents a fluorenyl group.
[0062] In the present invention, the term "substituted or unsubstituted" means a group selected from hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidine group, a hydrazine group, a hydrazone group, a carboxyl group or a carboxylate thereof, a sulfonic acid group or a sulfonate thereof, a phosphoric acid group or a phosphate thereof, a C1-C 40 Alkyl, C2-C 40 Alkenyl, C2-C 40 Alkynyl, C1-C 40 Alkoxy, C3-C 40 Cycloalkyl, C3-C 40 Cycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Aryl sulfide group and C2-C 60 The heterocyclic aryl group may be substituted or unsubstituted with one or more substituents, or may be substituted or unsubstituted with a substituent formed by linking two or more of the substituents exemplified above.
[0063] Alkyl within the meaning of the present invention is a straight-chain or branched alkyl radical having 1 to 40 carbon atoms, in which individual hydrogen atoms or -CH2- groups may also be substituted; and alkenyl or alkynyl having at least two carbon atoms. Alkyl, alkenyl or alkynyl is preferably taken to mean, by way of non-limiting example, the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
[0064] Alkoxy groups preferably having 1 to 40 carbon atoms are taken to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy.
[0065] Heteroalkyl is preferably an alkyl group having 1 to 40 carbon atoms and refers to a group in which a single hydrogen atom or -CH2- group is replaced by an oxygen, sulfur or halogen atom, and refers, as non-limiting examples, to alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, in particular to methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio thio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, hexynyloxy, and hexynylthio, ethynyloxy, ethynylthio, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, and hexynylthio.
[0066] Generally speaking, the cycloalkyl and cycloalkenyl groups according to the present invention can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, or cycloheptenyl, wherein one or more -CH2- groups can be replaced by the above groups; in addition, one or more hydrogen atoms can also be replaced by a deuterium atom, a halogen atom, or a nitrile group.
[0067] The heterocycloalkyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a non-aromatic hydrocarbon having 3 to 40 atomic nuclei. In this case, one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted with heteroatoms such as N, O, or S. Non-limiting examples include tetrahydrofuran, tetrahydrothiophene, morpholine, and piperazine.
[0068] The fused ring aromatic group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms and combining two or more rings. In this case, the two or more rings may be attached to each other in a simple or condensed form. Non-limiting examples thereof include phenanthrenyl, anthracenyl, fluoranthenyl, pyrenyl, triphenylene, perylene, Ji et al.
[0069] The arylamine group used in the present invention refers to an amine substituted with an aryl group having 6 to 60 carbon atoms. Non-limiting examples of arylamine groups include diphenylamine, N-phenyl-1-naphthylamine, and N-(1-naphthyl)-2-naphthylamine. A heteroarylamine group refers to an amine substituted with an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 2 to 60 carbon atoms. Non-limiting examples of heteroarylamine groups include N-phenylpyridin-3-amine, N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-2-amine, and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine.
[0070] The alkoxy group used in the present invention refers to RO - The monovalent functional group represented by R is an alkyl group having 1 to 40 carbon atoms, which may include a linear, branched, or cyclic structure. Non-limiting examples of such alkoxy groups include methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentyloxy, cyclopentyloxy, and cyclohexyloxy.
[0071] The aryloxy group used in the present invention refers to R'O - The monovalent functional group represented by is an aryl group having a carbon number of 6 to 60. Non-limiting examples of such an aryloxy group include phenoxy, naphthyloxy, biphenyloxy and the like.
[0072] The alkylsilyl group used in the present invention refers to a silyl group substituted by an alkyl group having 1 to 40 carbon atoms, wherein the number of carbon atoms constituting the alkylsilyl group is at least 3. Non-limiting examples of the alkylsilyl group include trimethylsilyl and triethylsilyl. The arylsilyl group refers to a silyl group substituted by an aryl group having 6 to 60 carbon atoms.
[0073] The arylphosphino group used in the present invention refers to a diarylphosphino group substituted with an aryl group having 6 to 60 carbon atoms. Non-limiting examples of arylphosphino groups include diphenylphosphino and bis(4-trimethylsilylphenyl)phosphino. An aryloxyphosphino group is a diarylphosphino group in which the phosphorus atom is oxidized to its highest valence state.
[0074] The arylboryl group used in the present invention refers to a diarylboryl group substituted with an aryl group having 6 to 60 carbon atoms. Non-limiting examples of the arylboryl group include diphenylboryl and di(2,4,6-trimethylphenyl)boryl. The alkylboryl group refers to a dialkylboryl group substituted with an alkyl group having 1 to 40 carbon atoms. Non-limiting examples of the alkylboryl group include di-tert-butylboryl and diisobutylboryl.
[0075] In the present invention, "ring" in the substituted or unsubstituted ring formed by the bonding of adjacent groups refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. A condensed ring refers to a condensed aliphatic ring, a condensed aromatic ring, a condensed aliphatic heterocycle, a condensed aromatic heterocycle, or a combination thereof.
[0076] The chain silicon compound represented by formula (I) of the present invention is preferably selected from the group consisting of the following structures:
[0077]
[0078]
[0079]
[0080] The symbols used have the same meanings as those defined above;
[0081] Preferably, Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 All are phenyl.
[0082] In some embodiments, the chain silicon compound is selected from the group consisting of the following compounds:
[0083]
[0084]
[0085] Wherein, T is selected from O, S, Se, CMe2, CPh2, CFlu, NPh, NPhPh, Me represents a methyl group, Ph represents a phenyl group, PhPh represents a biphenyl group, and Flu represents a fluorenyl group.
[0086] In some embodiments, the chain silicon compound is selected from the compounds represented by the following formulas J544-J660:
[0087]
[0088]
[0089]
[0090]
[0091]
[0092]
[0093] Part or all of the hydrogen in the above structure may be replaced by deuterium.
[0094] In some embodiments, the compounds of Formula I described herein may be at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated. As used herein, percent deuteration has its ordinary meaning and includes the percentage of all possible hydrogen atoms (e.g., hydrogen or deuterium positions) occupied by deuterium atoms. In some embodiments, one or more hole transport moieties are partially or completely deuterated. In some embodiments, one or more electron transport moieties are partially or completely deuterated. In some embodiments, one or more fused ring systems are partially or completely deuterated. In some embodiments, one or more non-fused rings are partially or completely deuterated. In some embodiments, one or more rings or fused rings containing one or more heteroatoms are partially or completely deuterated. In some embodiments, one or more fused or non-fused phenyl rings are partially or fully deuterated. In some embodiments, one or more alkyl or cycloalkyl groups are partially or fully deuterated.
[0095] The present disclosure encompasses any chemical structure comprising the chain silicon compound of the present disclosure or its monovalent or multivalent variant. In other words, the compound of the present invention or its monovalent or multivalent variant can be part of a larger chemical structure. Such chemical structures can be selected from the group consisting of: monomers, polymers, macromolecules and supramolecules (also referred to as supermolecules). As used herein, "monovalent variant of a compound" refers to a portion identical to the compound, but one of the hydrogen atoms has been removed and replaced with a bond to the rest of the chemical structure. As used herein, "multivalent variant of a compound" refers to a portion identical to the compound, but more than one hydrogen atoms has been removed and replaced with one or more bonds to the rest of the chemical structure. In the case of a supramolecule, the compound of the present invention can also be incorporated into a supramolecular complex without covalent bonds. As used in this context, the description that structure A includes part B means that structure A includes the structure of part B, and the structure of the part B does not include H or D atoms that can be connected to part B. This is because at least one H or D on a given moiety structure must be replaced with a substituent so that moiety B can be part of structure A, and after it becomes part of structure A, one or more of the H or D on a given moiety B structure can be further substituted.
[0096] The present invention also provides an organic electroluminescent material, the raw material of which includes the above-mentioned chain silicon compound; the organic electroluminescent material including the chain silicon compound of the present invention has the ability of carrier transport.
[0097] The present invention also provides the use of the above-mentioned chain silicon compound in the preparation of an organic electroluminescent element.
[0098] The present invention also provides an organic electroluminescent element, which includes: a first electrode, a second electrode, a capping layer and one or more organic layers disposed between the first electrode and the second electrode; the material of at least one of the organic layers or the capping layer includes the above-mentioned chain silicon compound.
[0099] The organic electroluminescent element comprises a cathode, an anode and at least one light-emitting layer. In addition to these layers, it may also comprise other layers, for example, in each case, comprising one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and / or charge generation layers. An intermediate layer having, for example, an exciton blocking function may also be introduced between two light-emitting layers. However, it should be noted that each of these layers does not necessarily have to be present. The organic electroluminescent device described herein may comprise one light-emitting layer, or it may comprise multiple light-emitting layers. That is, a variety of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred is a system with three light-emitting layers, wherein the three layers can display blue, green and red light emission. If there is more than one light-emitting layer, according to the present invention, at least one of these layers comprises the chain silicon compound of the present invention.
[0100] Furthermore, the organic electroluminescent element according to the present invention does not include a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, that is, the light-emitting layer is directly adjacent to the electron blocking layer or hole transport layer or anode, and / or the light-emitting layer is directly adjacent to the electron transport layer or electron injection layer or cathode.
[0101] In the other layers of the organic electroluminescent element according to the invention, in particular in the hole injection and hole transport layers as well as in the electron injection and electron transport layers, all materials can be used in the manner commonly used according to the prior art. A person skilled in the art will therefore be able to use all materials known for organic electroluminescent elements in combination with the emitting layer according to the invention without inventive step.
[0102] Furthermore, preference is given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation process, wherein the organic electroluminescent elements are applied in a vacuum sublimation apparatus at temperatures below 10 -5 Pa, preferably less than 10 -6 The material is applied by vapor deposition at an initial pressure of 10 Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa.
[0103] Likewise preferred are organic electroluminescent components in which one or more layers are applied by means of an organic vapor phase deposition method or by means of carrier gas sublimation, wherein at 10 -5 The material is applied at a pressure between 100 Pa and 1 Pa. A particular example of this method is the organic vapor jet printing method, in which the material is applied directly through a nozzle and is thus structured.
[0104] Furthermore, organic electroluminescent elements are preferred in which one or more layers are produced from solution, for example by spin coating, or by any desired printing method, such as screen printing, flexographic printing, lithographic printing, photoinduced thermography, thermal transfer printing, inkjet printing, or nozzle printing. Soluble compounds are obtained, for example, by suitable substitution. These methods are also particularly suitable for oligomers, dendrimers, and polymers. Hybrid methods are also possible, in which, for example, one or more layers are applied from solution and one or more additional layers are applied by vapor deposition.
[0105] These methods are generally known to those skilled in the art, and they can apply them to organic electroluminescent elements comprising the compounds according to the invention without inventive step.
[0106] The present invention therefore also relates to a method for producing an organic electroluminescent element according to the invention, applying at least one layer by means of a sublimation method and / or applying at least one layer by means of an organic vapor phase deposition method or by means of carrier gas sublimation and / or applying at least one layer from solution by spin coating or by means of a printing method.
[0107] The present invention also relates to a composition comprising at least one of the chain silicon compounds of the present invention as described above. The same preferences as described above for organic electroluminescent elements apply to the compounds of the present invention. In particular, the chain silicon compound may preferably contain other compounds in addition to the chain silicon compound. Liquid-phase processing of the heterocyclic compound of the present invention, for example, by spin coating or by printing methods, requires a formulation for processing the compounds of the present invention. These formulations may, for example, be solutions, dispersions, or emulsions. For this purpose, a mixture of two or more solvents may preferably be used. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenketone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpenes benzothiazole, butyl benzoate, isopropylbenzene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenethyl ether, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, or a mixture of these solvents.
[0108] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer or an electron blocking layer.
[0109] In some embodiments, the compound of the present invention may be a host, and the first organic layer may be an emissive layer comprising a phosphorescent or fluorescent emitter. As used herein, phosphorescence generally refers to the emission of photons when the electron spin quantum number changes, i.e., the initial and final states of the emission have different electron spin quantum numbers, such as from the T1 to the S0 state. Most iridium, platinum, or palladium complexes currently used in OLEDs are phosphorescent emitters. In some embodiments, if the exciplex formation involves a triplet emitter, such exciplexes may also emit phosphorescence. On the other hand, a fluorescent emitter generally refers to the emission of photons when the electron spin quantum number does not change, such as from the S1 to the S0 state or from the D1 to the D0 state. The fluorescent emitter may be a delayed fluorescent emitter or a non-delayed fluorescent emitter. Depending on the spin state, the fluorescent emitter may be a singlet emitter, a doublet emitter, or other multiplet emitter. It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. There are two types of delayed fluorescence, namely P-type and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA). On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but relies on the thermal population between the triplet and singlet excited states. Thermal energy can activate the triplet transition back to the singlet state. This type of delayed fluorescence is also called TADF. E-type delayed fluorescence characteristics can be found in exciplex systems or single compounds. Without being bound by theory, it is believed that TADF emission needs to have a small singlet-triplet energy gap (ΔE) of less than or equal to 400, 350, 300, 250, 200, 150, 100 or 50 meV. S-T ) compounds or excited complexes. There are two main types of TADF emitters, one is called donor-acceptor type TADF and the other is called multi-resonance (MR) TADF. Typically, a single compound donor-acceptor TADF compound is constructed by connecting an electron donor portion (such as an amino or carbazole derivative) and an electron acceptor portion (such as a nitrogen-containing six-membered aromatic ring or a cyano-substituted aromatic ring). A donor-acceptor excited complex can be formed between a hole transport compound and an electron transport compound. Examples of MR-TADF materials include highly conjugated fused ring systems. In some embodiments, MR-TADF materials contain boron, carbon, and nitrogen atoms. Such materials may also contain other atoms, such as oxygen, sulfur, and selenium. In some embodiments, the reverse intersystem crossing time from T1 to S1 of delayed fluorescence emission at 293K is less than or equal to 10 microseconds. In some embodiments, such time may be greater than 10 microseconds and less than 100 microseconds.
[0110] In some embodiments, the compound of the present invention is a host, and the organic layer is an emissive layer comprising a phosphorescent or fluorescent material.
[0111] In some embodiments, the emissive dopant may be a phosphorescent or fluorescent material.
[0112] In some embodiments, the non-emissive dopant may also be a phosphorescent or fluorescent material.
[0113] In some embodiments, the OLED can include additional compounds selected from the group consisting of: non-delayed fluorescent materials, delayed fluorescent materials, phosphorescent materials, and combinations thereof.
[0114] In some embodiments, the phosphorescent material is an emitter that emits light within the OLED. In some embodiments, the phosphorescent material does not emit light within the OLED. In some embodiments, the phosphorescent material transfers energy from its excited state to another material within the OLED. In some embodiments, the phosphorescent material participates in charge transport within the OLED. In some embodiments, the phosphorescent material is a sensitizer or a component of a sensitizer, and the OLED further comprises an acceptor. In some embodiments, the phosphorescent material forms an exciplex with another material within the OLED (e.g., a host material, an emitter material).
[0115] In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material is an emitter that emits light within the OLED.
[0116] In some embodiments, the non-delayed fluorescent material or delayed fluorescent material does not emit light within the OLED. In some embodiments, the non-delayed fluorescent material or delayed fluorescent material energy transfers its excited state to another material within the OLED. In some embodiments, the non-delayed fluorescent material or delayed fluorescent material participates in charge transport within the OLED. In some embodiments, the non-delayed fluorescent material or delayed fluorescent material is an acceptor, and the OLED further comprises a sensitizer.
[0117] In some embodiments, the compound of the present invention may be an acceptor, and the OLED may further comprise a sensitizer selected from the group consisting of delayed fluorescent materials, phosphorescent materials, and combinations thereof.
[0118] In some embodiments, the compounds of the present invention can be non-delayed fluorescent emitters, delayed fluorescent emitters, or components of exciplexes that are non-delayed fluorescent emitters or delayed fluorescent emitters. In some embodiments, the emission of the compounds of the present invention at room temperature has a full width at half maximum (FWHM) of equal to or less than 50, 45, 40, 35, 30, 25, 20, 15, 10, or 5 nm. A narrower FWHM means better color purity for OLED display applications.
[0119] In some embodiments, a compound of the present invention is a host and the OLED comprises an acceptor as an emitter and a sensitizer selected from the group consisting of a delayed fluorescent material, a phosphorescent material, and combinations thereof; wherein the sensitizer transfers energy to the acceptor.
[0120] In some embodiments, the phosphorescent material may be a metal coordination complex having a metal-carbon bond, a metal-nitrogen bond, or a metal-oxygen bond. In some embodiments, the metal is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Zn, Au, Ag, and Cu. In some embodiments, the metal is Ir. In some embodiments, the metal is Pt. In some embodiments, the metal is Pd, Cu, Ag, or Au. In some embodiments, the phosphorescent material has the formula M(L 3 ) x (L 4 ) y (L 5 ) z ;
[0121] Among them L 3 、L 4 and L 5 Can be the same or different;
[0122] where x is 1, 2, or 3;
[0123] where y is 0, 1, or 2;
[0124] where z is 0, 1, or 2;
[0125] wherein x+y+z is the oxidation state of the metal M; regarding the oxidation state of the metal M, when M is Ir, the oxidation valence state of Ir may be 3, and when M is Pt, the oxidation valence state of Pt may be 2.
[0126] Among them L 3 、L 4 Selected from the group consisting of:
[0127]
[0128]
[0129] Among them L 5 Selected from the group consisting of:
[0130]
[0131] M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Zn, Au, Ag and Cu; preferably, M is selected from Ir or Pt;
[0132] Y 1 is a direct bond or is selected from the group consisting of NR, PR, O, S and Se; preferably, the Y 1 is a direct key or O;
[0133] Y 2 Selected from the group consisting of BR, NR, PR, O, S, Se, C=O, S=O, SO2, CR2, SiR2 and GeR2; two adjacent Rs may be joined or fused to form a ring;
[0134] R independently represents monosubstitution, polysubstitution to the maximum possible number of substitutions, or no substitution;
[0135] Each R is independently hydrogen, deuterium, or a substituent selected from the group consisting of general substituents defined herein; and any two substituents can be fused or joined to form a ring or a multidentate ligand. In some embodiments, the phosphorescent material has a structural formula selected from the group consisting of: Ir(L 3 )3、Ir(L 3 )(L 4 )2、Ir(L 3 )2(L 4 )、Ir(L 3 )2(L 5 )、Ir(L 3 )(L 4 )(L 5 ) and Pt(L 3 )(L 4 ); where L 3 、L 4 and L 5 Different from each other in Ir compounds;
[0136] Among them L 3 and L 4 may be the same or different in the Pt compound; and wherein L 3 and L 4 capable of linking to form a tetradentate ligand in the Pt compound.
[0137] In some embodiments, the phosphorescent material has a structure shown in Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, Formula XI, Formula XII, Formula XIII, or Formula XIV:
[0138]
[0139] Where R and Y 2 The meaning of is the same as the aforementioned definition, and the metal Pt may be replaced by Pd.
[0140] In some embodiments of the OLED, the delayed fluorescent material comprises at least one donor group and at least one acceptor group. In some embodiments, the delayed fluorescent material is a metal complex. In some embodiments, the delayed fluorescent material is a non-metal complex. In some embodiments, the delayed fluorescent material is a Zn, Cu, Ag, or Au complex.
[0141] In some embodiments, the delayed fluorescent material comprises at least one acceptor moiety selected from the group consisting of nitrile, isonitrile, borane, fluoride, pyridine, pyrimidine, pyrazine, triazine, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-triphenylene, imidazole, pyrazole, oxazole, thiazole, isoxazole, isothiazole, triazole, thiadiazole, and oxadiazole. In some embodiments, the acceptor moiety and the donor moiety as described herein can be directly linked, via a conjugated linker or a non-conjugated linker such as sp 3 carbon or silicon atoms) connected.
[0142] In some embodiments, the OLEDs or emission regions comprising the compounds of the present invention disclosed herein can be incorporated into a full-color pixel arrangement of a device. The full-color pixel arrangement of such a device comprises at least one pixel, wherein the at least one pixel comprises a first subpixel and a second subpixel. The first subpixel comprises a first OLED comprising a first emission region. The second subpixel comprises a second OLED comprising a second emission region. In some embodiments, the first and / or second OLED, the first and / or second emission regions may be the same or different and each may independently have various device features and various embodiments of the compounds of the present invention included therein, as well as various combinations and sub-combinations of various device features and various embodiments of the compounds of the present invention included therein, as disclosed herein.
[0143] In some embodiments, the first emission region is configured to emit light having a peak wavelength λ max1 The second emission region is configured to emit light having a peak wavelength λ max2 In some embodiments, the peak wavelength λ max1 and λ max2 The difference between the two is at least 4 nm, but within the same color. For example, light blue and dark blue light as described above. In some embodiments, the first emission region is configured to emit light having a peak wavelength λ in one region of the visible spectrum of 400-500 nm, 500-600 nm, 600-700 nm. max1 and the second emission region is configured to emit light having a peak wavelength λ in one of the remaining regions of the visible spectrum of 400 to 500 nm, 500 to 600 nm, 600 to 700 nm; max2In some embodiments, the first emitting region comprises (if more than one) a first number of emitting layers deposited one above the other; and the second emitting region comprises (if more than one) a second number of emitting layers deposited one above the other; and the first number is different from the second number.
[0144] In some embodiments, the first emission region and the second emission region both comprise phosphorescent materials, which may be the same or different. In some embodiments, the first emission region comprises a phosphorescent material and the second emission region comprises a fluorescent material. In some embodiments, the first emission region and the second emission region both comprise fluorescent materials, which may be the same or different.
[0145] In some embodiments, the OLED or at least one pixel of the emissive region includes a total of N subpixels; wherein the N subpixels include a first subpixel and a second subpixel; wherein each of the N subpixels includes an emissive region; wherein the total number of emissive regions within the at least one pixel is equal to or less than N-1. In some embodiments, the second emissive region is identical to the first emissive region; and each subpixel of the at least one pixel includes an emissive region that is identical to the first emissive region. In some embodiments, a full-color pixel arrangement can have a plurality of pixels including a first pixel region and a second pixel region; wherein at least one display feature in the first pixel region is different from a corresponding display feature in the second pixel region, and wherein the at least one display feature is selected from the group consisting of: resolution, cavity mode, color, outcoupling, and color filter.
[0146] In some embodiments, the OLED is a stacked OLED comprising one or more charge generation layers (CGLs). In some embodiments, the OLED comprises a first electrode, a first emission region disposed above the first electrode, a first CGL disposed above the first emission region, a second emission region disposed above the first CGL, and a second electrode disposed above the second emission region. In some embodiments, the first emission region and / or the second emission region may have various device features as described above for pixelated devices. In some embodiments, the stacked OLED is configured to emit white. In some embodiments, one or more of the emission regions in the pixelated OLED or stacked OLED comprises a sensitizer and an acceptor having various sensitizing device features and various embodiments of the compounds of the present invention disclosed herein. For example, the first emission region is included in the sensitizing device, while the second emission region is not included in the sensitizing device; in some cases, both the first emission region and the second emission region are included in the sensitizing device.
[0147] The present invention also provides a consumer product comprising the organic electroluminescent element described above. The consumer product described in the present invention can be one of the following devices: a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a lamp for internal or external lighting and / or signaling, a head-up display, a fully transparent or partially transparent display, a flexible display, a laser printer, a telephone, a cellular phone, a tablet computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay with a diagonal of less than 2 inches, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, a light therapy device, and a sign.
[0148] In addition, unless otherwise specified, the raw materials used in the present invention can be obtained commercially, and any range recorded in the present invention includes the end value and any numerical value between the end values and any sub-range formed by the end value or any numerical value between the end values.
[0149] The beneficial effects achieved by the present invention are:
[0150] The chain silicon compound represented by formula (I) provided by the present invention can be applied to the organic layer of an organic electroluminescent device due to its excellent electron mobility, thermal stability, and luminescent properties. In particular, when the chain silicon compound represented by formula (I) of the present invention is used in the electron transport layer, electron transport auxiliary layer, and light-emitting layer, it is possible to produce an organic electroluminescent device with lower driving voltage, higher efficiency, and longer life than conventional electron transport materials. Furthermore, it is also possible to produce a full-color display panel with improved performance and life. BRIEF DESCRIPTION OF THE DRAWINGS
[0151] Figure 1 A schematic diagram of an organic light-emitting device 100 is shown. Device 100 includes a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, an organic light-emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. Device 100 can be fabricated by depositing the described layers in sequence.
[0152] Figure 2Schematic diagram of an organic light-emitting device 200 showing two light-emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light-emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. Device 200 can be fabricated by sequentially depositing the described layers. The emission peaks of the first and second light-emitting layers of device 200 can overlap, overlap, or be non-overlapping. Materials similar to those described for device 100 can be used in the corresponding layers of device 200. DETAILED DESCRIPTION
[0153] The following examples are used to illustrate the present invention but are not intended to limit the scope of the present invention.
[0154] In the description of the present invention, unless otherwise specified, “plurality” means two or more; the orientations or positional relationships indicated by the terms “upper”, “lower”, etc. are based on the orientations or positional relationships shown in the accompanying drawings, and are only for the convenience of describing the present invention and simplifying the description, rather than indicating or implying that the device or element referred to must have a specific orientation, be constructed and operate in a specific orientation, and therefore cannot be understood as a limitation on the present invention.
[0155] Unless otherwise specified, the experimental methods used in the following examples are all conventional methods. The experimental raw materials and related equipment used in the following examples are all commercially available, unless otherwise specified, and the percentages are all weight percentages unless otherwise specified.
[0156] The following examples use the following testing instruments and methods to test the performance of OLED materials and components:
[0157] OLED component performance test conditions:
[0158] Brightness and chromaticity coordinates: tested using a spectrum scanner PhotoResearch PR-715;
[0159] Current density and turn-on voltage: tested using a Keithley 2420 digital source meter;
[0160] Power efficiency: Tested using NEWPORT 1931-C.
[0161] Example 1
[0162] The preparation method of compound J591 comprises the following steps:
[0163] Step 1: Preparation of intermediate Int-1
[0164]
[0165] Under nitrogen, 20.0 mmol of compound sub-1 was dissolved in 80 mL of dry THF, cooled to -78°C, and 22.0 mmol of a 2.5 M n-butyllithium solution in n-hexane was added dropwise. The reaction was stirred for 30 minutes. 22.0 mmol of compound sub-2 was quickly added, the temperature was slowly raised to room temperature, and the reaction was stirred for 12 hours. 40 mL of saturated aqueous ammonium chloride was added, and the mixture was extracted with ethyl acetate. The organic phase was dried and filtered. The filtrate was concentrated under reduced pressure to dryness and then purified using a silica gel column to obtain compound Int-1 as a white solid in a yield of 71%.
[0166] Step 2: Preparation of compound J591
[0167]
[0168] Under nitrogen, 20.0 mmol of compound sub-3 was dissolved in 80 mL of dry THF, cooled to -78°C, and 22.0 mmol of a 2.5 M n-butyllithium solution in n-hexane was added dropwise. The reaction was stirred for 30 minutes. 20.0 mmol of compound Int-1 was quickly added, the temperature was slowly raised to room temperature, and the reaction was stirred for 12 hours. 40 mL of saturated aqueous ammonium chloride was added, the organic phase was separated, and the aqueous phase was extracted with dichloromethane. The organic phases were combined, dried, filtered, and the filtrate was concentrated under reduced pressure to dryness. Compound J591 was obtained as a white solid in a 64% yield. MS (TOF) m / z: 915.3275 [M+H]. 1 HNMR (δ, CDCl3): 8.85(2H,s); 8.64(1H,s); 8.56~8.52(2H,m); 8.45~8.42(1H,m); 8.08~8.06(2H,m); 7.89(1H,s); 7.76~7.72 (2H,m); 7.69~7.65(3H,m); 7.63~7.58(10H,m); 7.55~7.51(2H,m); 7.45~7.41(3H,m); 7.39~7.37(2H,m); 7.23~7.15(15H,m).
[0169] Example 2
[0170] Preparation of compound J555:
[0171]
[0172] Under nitrogen protection, 20.0 mmol of compound sub-4 was dissolved in 80 mL of dry THF, cooled to -78 ° C, and 22.0 mmol of 2.5 M n-butyl lithium n-hexane solution was added dropwise, and the reaction was stirred for 30 minutes. 20.0 mmol of compound Int-2 (prepared by the synthesis method of the first step of Example 1) was quickly added, slowly warmed to room temperature, and stirred for 12 hours. 40 mL of saturated ammonium chloride aqueous solution was added, the organic phase was separated, the aqueous phase was extracted with dichloromethane, the organic phases were combined and dried, filtered, and the filtrate was concentrated and dried under reduced pressure, and separated and purified by silica gel column to obtain compound J555.
[0173] T=NPh, yellow solid, yield: 72%. MS (TOF) m / z: 760.2802 [M+H]; 1 HNMR(δ, CDCl3): 8.39(1H,s); 7.98(1H,s); 7.86~7.82(4H,m); 7.68~7.64(10H,m); 7.55~7.53(1H,d ); 7.49~7.46(4H,m); 7.44~7.42(1H,d); 7.39~7.33(3H,m); 7.31~7.28(1H,m); 7.23~7.15(15H,m).
[0174] Preparation of Compound 555-1 to Compound 555-4
[0175] The preparation method is the same as compound 555, except that compounds sub-4-1, sub-4-2, sub-4-3 and sub-4-4 are used respectively instead of compound sub-4.
[0176]
[0177] White solid, yield: 75%. MS (TOF) m / z: 685.2317 [M+H]; 1 HNMR(δ, CDCl3): 8.01(1H,s); 7.95(1H,s); 7.86~7.82(4H,m); 7.68~7.64(10H,m); 7.62~7 .60(1H,d); 7.56~7.54(1H,m); 7.46~7.44(1H,d); 7.38~7.33(2H,m); 7.23~7.15(15H,m).
[0178]
[0179] White solid, yield: 73%. MS (TOF) m / z: 701.2088 [M+H]; 1HNMR (δ, CDCl3): 8.26(1H,s); 8.14(1H,s); 7.86~7.82(5H,m); 7.80~7.78(1H,d); 7.72~7. 70(1H,d); 7.68~7.64(10H,m); 7.62~7.60(1H,d); 7.44~7.40(1H,m); 7.23~7.15(15H,m).
[0180]
[0181] White solid, yield: 68%. MS (TOF) m / z: 711.2839 [M+H]; 1 HNMR (δ, CDCl3): 8.17 (1H, s); 8.02~8.00 (1H, d); 7.85~7.80 (4H, m); 7.69~7.62 ( 10H,m); 7.42~7.38(4H,m); 7.23~7.15(15H,m); 7.12~7.08(1H,m); 1.68(6H,s).
[0182]
[0183] White solid, yield: 65%. MS (TOF) m / z: 833.2996 [M+H]; 1 HNMR (δ, CDCl3): 8.09 (1H, s); 7.92~7.88 (3H, m); 7.64~7.62 (1H, d); 7.56 ~7.50(6H,m); 7.44~7.38(10H,m); 7.36~7.27(18H,m); 7.24~7.18(5H,m).
[0184] Example 3
[0185] The preparation of compound J634 comprises the following steps:
[0186] Step 1: Preparation of intermediate Int-3
[0187]
[0188] Under nitrogen, 20.0 mmol of 3,5-dibromochlorobenzene was dissolved in 80 mL of dry THF, cooled to -78°C, and 22.0 mmol of a 2.5 M n-butyllithium solution in n-hexane was added dropwise. The reaction was stirred for 30 minutes. 22.0 mmol of triphenylsilyl chloride was added dropwise, the temperature was slowly warmed to room temperature, and the reaction was stirred for 1 hour. The temperature was cooled to -78°C, and 22.0 mmol of a 2.5 M n-butyllithium solution in n-hexane was added dropwise. The reaction was stirred for 30 minutes. 22.0 mmol of triphenylsilyl chloride was added dropwise, the temperature was slowly warmed to room temperature, and the reaction was stirred for 1 hour. 40 mL of saturated aqueous ammonium chloride was added, and the mixture was extracted with ethyl acetate. The organic phase was dried and filtered. The filtrate was concentrated under reduced pressure to dryness and then purified using a silica gel column to obtain compound Int-3 as a white solid in a yield of 53%.
[0189] Step 2: Preparation of intermediate Int-4
[0190]
[0191] Under nitrogen, 20.0 mmol of compound Int-3 was dissolved in 50 mL of dry DMF. 24.0 mmol of anhydrous sodium acetate, 22.0 mmol of pinacol diboronate, 0.2 mmol of Pd(dba)2, and 0.4 mmol of XPhos were added. The temperature was raised to 110°C and stirred for 12 hours. The mixture was cooled to room temperature, and 150 mL of saturated aqueous ammonium chloride was added. The mixture was extracted with ethyl acetate, the organic phase was dried, filtered, and the filtrate was concentrated under reduced pressure to dryness. The mixture was then purified on a silica gel column to obtain compound Int-4 as a white solid in a 92% yield.
[0192] Step 3: Preparation of compound J634
[0193]
[0194] Under nitrogen, 22.0 mmol of compound Int-4 prepared in the previous step, 20.0 mmol of compound Sub-5, and 40 mL of toluene were mixed. 50.0 mmol of anhydrous potassium carbonate, 0.01 mmol of Pd132 catalyst, 20 mL of water, and 20 mL of ethanol were added, and the mixture was stirred at reflux for 15 hours. The mixture was cooled to room temperature, 50 mL of water was added, and the organic phase was separated. The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. Compound J634 was obtained as a light yellow solid in a 68% yield. MS (TOF) m / z: 1080.3853 [M+H]. 1HNMR (δ, CDCl3): 8.87(1H,s); 8.74(1H,s); 8.58~8.54(2H,m); 8.28(1H,s); 8.12~8.06(3H,m); 7.97~7.95(2H,m); 7 .63~7.58(12H,m); 7.55~7.51(1H,m); 7.45~7.41(3H,m); 7.39~7.38(1H,d); 7.36~7.28(8H,m); 7.23~7.15(18H,m).
[0195] Example 4
[0196] An OLED element is provided, and a preparation method thereof comprises the following steps:
[0197] 1) A glass substrate coated with an ITO conductive layer was ultrasonically treated in a cleaning agent for 30 minutes, rinsed in deionized water, ultrasonically treated in an acetone / ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dry, irradiated with an ultraviolet light cleaner for 10 minutes, and bombarded with a low-energy cation beam.
[0198] 2) Place the treated ITO glass substrate in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10 -5 Pa, metallic silver is evaporated on the above ITO film as the anode, and the thickness of the evaporated film is Continue to evaporate compound HI01 and F4TCNQ as hole injection layer, wherein compound F4TCNQ is 3% of HI01 mass and the evaporation film thickness is
[0199] 3) Continue to evaporate the compound HTM on the hole injection layer to form a hole transport layer with a thickness of
[0200] 4) Continue to evaporate the compound EBL on the hole transport layer to form an electron blocking layer with a film thickness of
[0201] 5) The chain silicon compound of the present invention is continuously evaporated on the electron blocking layer as the main material and the compound BD012 is used as the doping material. The mass ratio of the compound BD012 to the chain silicon compound is 1:9. The organic light-emitting layer of the element is formed. The film thickness of the organic light-emitting layer obtained by evaporation is
[0202] 6) Continue to evaporate a layer of compound LiQ and ET025 on the organic light-emitting layer as the electron transport layer of the element, wherein the mass ratio of compound ET025 to LiQ is 1:1, and the evaporated film thickness is
[0203] 7) Continue to evaporate a layer of LiF on the electron transport layer as the electron injection layer, and the evaporated film thickness is
[0204] 8) On the electron injection layer, magnesium and silver are evaporated as the transparent cathode layer of the element. The mass ratio of magnesium to silver is 1:10, and the thickness of the evaporated film is
[0205] 9) On top of the transparent cathode layer, a layer of CPD is evaporated as the CPL layer of the element. The thickness of the evaporated film is The OLED element provided by the present invention is obtained.
[0206] The structure of the compound used in Example 4 is as follows:
[0207]
[0208] Comparative Example 1
[0209] The same steps as in Example 4 were followed, except that the chain silicon compound of the present invention in step 5) was replaced with the comparative compound H01 to obtain a comparative element 1;
[0210]
[0211] The organic electroluminescent element prepared by the above process was subjected to the following performance tests:
[0212] The driving voltage, current efficiency and life of the organic electroluminescent elements prepared in Example 4 and Comparative Example 1 were measured using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1 V per second, and the luminance of the organic electroluminescent element was measured when it reached 1000 cd / m 2 The voltage at which the luminance is measured is the driving voltage, and the current density at this time is measured at the same time; the ratio of brightness to current density is the current efficiency; the LT95% life test is as follows: use a luminance meter at 1000cd / m 2 Under the same brightness, the current is kept constant and the brightness decay of the organic electroluminescent element is measured to be 950cd / m 2 The data listed in Table 1 are relative data compared with comparative element 1.
[0213] Table 1
[0214]
[0215]
[0216]
[0217] As shown in Table 1, the device prepared from the chain silicon compound of the present invention has a lower driving voltage than H01 at the same brightness, and the current efficiency is significantly improved, reaching up to 1.2 times that of the comparative device. In addition, the LT95% life of the device is significantly improved, indicating that the chain silicon compound of the present invention is an excellent electroluminescent layer material.
[0218] Although the present invention has been described in detail above using general descriptions and specific embodiments, it will be apparent to those skilled in the art that modifications and improvements may be made based on the present invention. Therefore, such modifications and improvements, which do not depart from the spirit of the present invention, are intended to be within the scope of protection claimed herein.
Claims
1. A chain silicon compound, the structural formula of which is shown in formula (I): in, L 1 Selected from substituted or unsubstituted C6-C 60 Arylene, substituted or unsubstituted C2-C 60 A group consisting of a heteroarylene group, or an amino group; L 2 Each independently selected from a single bond, a substituted or unsubstituted C6-C 60 Arylene, or substituted or unsubstituted C2-C 60 The group consisting of heteroarylene; n represents an integer from 1 to 5; m represents an integer from 0 to 5; Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Each independently selected from substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Arylamine, or substituted or unsubstituted C2-C 60 The group consisting of heteroaryl groups; Het represents a substituted or unsubstituted C2-C 60 Heteroaryl, substituted or unsubstituted C6-C 60 aryl; Optionally, L 1 、L 2 、Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 The substituents substituted in Het are each independently selected from hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, amidine, hydrazine, hydrazone, carboxyl or its carboxylate, sulfonic acid or its sulfonate, phosphate or its phosphate, C1-C 40 Alkyl, C2-C 40 Alkenyl, C2-C 40 Alkynyl, C1-C 40 Alkoxy, C3-C 40 Cycloalkyl, C3-C 40 Cycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Aryl sulfide group and C2-C 60 Any one or a combination of at least two of the heterocyclic aromatic groups.
2. The chain silicon compound according to claim 1, characterized in that The Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Each independently selected from substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 The group consisting of heteroaryl groups; Preferably, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 are each independently selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, pyrenyl, phenyl, fluorenyl, peryl, fluoranthenyl, tetraphenyl, pentacene, benzopyrenyl, biphenyl, phenylene, terphenyl, triphenyl, quadriphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, triphenylene, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, cis- or trans-indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzocarbazolyl, dibenzocarbazolyl, azadibenzo[g,ij]naphtho[2,1,8-cde]azulene, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, spiroistrimerized indenyl, furanyl, benzofuranyl, isobenzofuran yl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo[5,6]quinolyl, benzo[6,7]quinolyl, benzo[7,8]quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, isoxazolyl, 1 ,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazatriphenylene radical, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorescein ring radical, naphthyridinyl, azacarbazolyl, benzocarbolinyl, carbolinyl, phenanthroline radical, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazole oxazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl or a group derived from a combination of these systems; More preferably, Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl; Optionally, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 The substituents substituted in the 10 Alkyl, C3-C 10 Cycloalkyl, C6-C 20 Aryl, C3-C 20 Any one or a combination of at least two of the heteroaryl groups is preferably selected from any one of deuterium, halogen, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, sec-butyl, tert-butyl, deuterated tert-butyl, isobutyl, isopentyl, tert-pentyl, cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, naphthyl, and pyridyl.
3. The chain silicon compound according to claim 1 or 2, characterized in that The Het are each independently selected from substituted or unsubstituted C2-C 30 Heteroaryl, substituted or unsubstituted C6-C 30 A group consisting of aromatic groups; Preferably, the Het is selected from the group consisting of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, pyrenyl, phenyl, benzothiophene, benzopyrenyl, biphenyl, phenylene, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, triphenylene, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo[5 ,6]quinolyl, benzo[6,7]quinolyl, benzo[7,8]quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, isoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazatriphenylenyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoline Oxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorescein ring group, naphthyridinyl, azacarbazolyl, benzocarbolinyl, carbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl or a group derived from a combination of these systems; Optionally, the substituents substituted in the Het are independently selected from deuterium, halogen, cyano, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C6-C 20 Aryl, C3-C 20 Any one or a combination of at least two of the heteroaryl groups.
4. The chain silicon compound according to any one of claims 1 to 3, characterized in that The Het is selected from the group consisting of the following groups shown in II-1 to II-13: in, Z1 and Z2 are each independently selected from hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, amidine, hydrazine, hydrazone, carboxyl or its carboxylate, sulfonic acid or its sulfonate, phosphate or its phosphate, C1-C 40 Alkyl, C2-C 40 Alkenyl, C2-C 40 Alkynyl, C1-C 40 Alkoxy, C3-C 40 Cycloalkane, C3-C 40 Cycloalkene, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Aryl sulfide, substituted or unsubstituted C6-C 60 Arylamine, or substituted or unsubstituted C2-C 60 A group consisting of heteroaryl groups; adjacent Z1s are not connected or are connected to form a ring through chemical bonds, and adjacent Z2s are not connected or are connected to form a ring through chemical bonds; x1 represents an integer from 1 to 4; x2 represents an integer from 1 to 3; x3 represents 1 or 2; x4 represents an integer from 1 to 6; x5 represents an integer from 1 to 5; T1 and T2 represent O, S, CR'R" or NAr'; R', R" are each independently selected from hydrogen, C1-C 60 Alkyl, C1-C 60 Heteroalkyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Arylamine, or substituted or unsubstituted C2-C 60 A group consisting of heteroaryl groups, R' and R" may be optionally joined or fused to form one or more additional substituted or unsubstituted rings, containing or not containing one or more heteroatoms N, P, B, O or S in the formed rings; preferably, R', R" are hydrogen, methyl, phenyl or fluorenyl; Ar' is selected from C1~C 40 Alkyl, C1~C 40 Heteroalkyl, C3~C 40 Cycloalkyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C 10 -C 60 Condensed ring aromatic group, substituted or unsubstituted C6-C 60 Arylamine, or substituted or unsubstituted C2-C 60 The group consisting of heteroaryl; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl; Optionally, the substituents substituted in Z1, Z2, R', R", and Ar' are independently selected from deuterium, halogen, cyano, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C6-C 20 Aryl, C3-C 20 Any one or a combination of at least two of heteroaryl groups; Indicates the attachment site of a group.
5. The chain silicon compound according to any one of claims 1 to 4, characterized in that The L 1 、L 2 Each independently selected from any one of the following formulas (20) to (35): wherein Y is selected from O, S, SO, SO2, Se, CR'R", SiR'R" or NAr'; R represents one, two or more to saturated substitution, and each is independently selected from hydrogen, deuterium, halogen atoms, hydroxyl, nitrile, nitro, amino, amidine, hydrazine, hydrazone, carboxyl or its carboxylate, sulfonic acid or its sulfonate, phosphoric acid or its phosphate, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Cycloalkane, C3-C 60 Cycloalkene, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Aryl sulfide group, or substituted or unsubstituted C2-C 60 The group consisting of heteroaryl groups; R', R" are each independently selected from hydrogen, C1-C 60 Alkyl, C1-C 60 Heteroalkyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Arylamine, or substituted or unsubstituted C2-C 60 A group consisting of heteroaryl groups, R' and R" may be optionally joined or fused to form one or more additional substituted or unsubstituted rings, containing or not containing one or more heteroatoms N, P, B, O or S in the formed rings; preferably, R', R" are hydrogen, methyl, phenyl or fluorenyl; Ar' is selected from C1-C 60 Alkyl, C1-C 60 Heteroalkyl, C3-C 60 Cycloalkyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Condensed ring aromatic group, substituted or unsubstituted C6-C 60 Arylamine, or substituted or unsubstituted C2-C 60 The group consisting of heterocyclic aromatic groups; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl; Optionally, the substituents substituted in R, R', R", and Ar' are independently selected from deuterium, halogen, cyano, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C6-C 20 Aryl, C3-C 20 Any one or a combination of at least two of heteroaryl groups; Dashed lines represent the sites of attachment of the groups.
6. The chain silicon compound according to any one of claims 1 to 5, characterized in that The chain silicon compound is selected from the group consisting of the following compounds: T is selected from O, S, Se, CMe2, CPh2, CFlu, NPh, NPhPh, Me represents a methyl group, Ph represents a phenyl group, PhPh represents a biphenyl group, and Flu represents a fluorenyl group.
7. The chain silicon compound according to any one of claims 1 to 5, characterized in that The chain silicon compound is selected from the compounds shown in the following formulas J544-J660: Part or all of the hydrogen in the above structure may be replaced by deuterium.
8. Use of the chain silicon compound according to any one of claims 1 to 7 in the preparation of an organic electroluminescent element.
9. An organic electroluminescent element comprising a first electrode, a second electrode, a capping layer, and an organic layer disposed between the first electrode and the second electrode; the material of at least one of the organic layer and / or the capping layer comprises the chain silicon compound according to any one of claims 1 to 7; Preferably, the organic layer includes a hole injection layer, a hole transport layer, a hole blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer or an electron blocking layer; the light-emitting layer, the electron transport layer or the hole blocking layer includes the chain silicon compound according to any one of claims 1 to 7.
10. A consumer product, characterized in that: It comprises the organic electroluminescent element according to claim 9.