A composition for a light-emitting layer and an organic electroluminescent device comprising the same
By using a combination of a host material with a specific structure and a double boron fluorescent material in OLED green light devices, the electron-hole balance is optimized, solving the problems of low efficiency and short lifespan of green light devices, and realizing high-efficiency and long-life green light display.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- JIANGSU SUNERA TECH CO LTD
- Filing Date
- 2024-12-30
- Publication Date
- 2026-06-30
AI Technical Summary
Among existing OLED green light devices, phosphorescence technology suffers from low efficiency and short lifespan, making it difficult to meet the display requirements of high color purity and narrow half-width. Furthermore, the carrier material bears high charge pressure, resulting in unbalanced energy transfer.
A light-emitting layer composition consisting of a first host material, a second host material, and a double-boron fluorescent material with a specific structure is used to optimize electron-hole balance and exciton quenching, thereby improving device efficiency and lifetime.
It improves the efficiency and lifespan of OLED green light devices, meets the display standards of high color purity and narrow half-width, and solves the bottleneck problems of efficiency and lifespan of traditional phosphorescent materials.
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Figure CN122318718A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of display lighting technology, and more particularly to a composition for a light-emitting layer and an organic electroluminescent device comprising the same. Background Technology
[0002] Organic light-emitting diodes (OLEDs) offer significant advantages over liquid crystal displays (LCDs), including being lighter and thinner, having higher color contrast, lower power consumption, faster response times, higher resolution, and greater flexibility. They are considered poised to dominate future display terminal products. With the advent of the 5G era, the new information display industry urgently needs to evolve. Early color gamut standards (BT.709 and DCIP3) are no longer sufficient to meet the high-quality technological demands of display products. To achieve ultra-high definition and higher image quality, the new generation display standard (BT.2020) is driving the development of OLED luminescent materials towards higher color purity, requiring core luminescent materials to have a narrower emission spectrum. Currently, among the three commercially available OLED color display technologies (red, green, and blue), blue light uses traditional phosphorescent triplet-triplet-transition (TTF) technology. This technology has lower efficiency but higher color purity, and it has basically met the BT.2020 display specifications. Green and red light use phosphorescence technology, which has high efficiency, and red light is close to the BT.2020 display specifications. However, traditional green light display technology relies on phosphorescence, resulting in a wider emission spectrum and a higher relative peak height. In commercially available OLED green light devices, the top-to-bottom emission efficiency flip-flop ratio is sacrificed. Therefore, the final efficiency and lifespan of the devices are significantly limited, and it is difficult to achieve a narrower half-width and color purity, which is far from meeting the requirements of high-definition display specifications. Therefore, it is crucial to develop a new generation of green light display technology and apply it to green light devices.
[0003] In traditional phosphorescent devices, the only carrier in the light-emitting layer is the phosphorescent material. Therefore, the material bears extremely high charge pressure, and the energy transfer and transmission process in the device is relatively simple.
[0004] Since 2020, green fluorescent materials with narrow half-width at half-maximum (WHM < 30 nm) based on boron-nitrogen resonant structures have been reported successively. Furthermore, several papers on green boron-nitrogen narrow emission materials and device effects were reported in 2022 and 2023, such as DOI: 10.1002 / anie.202301930, DOI: 10.1038 / s41566-022-01106-8, DOI: 10.1002 / anie.202313254, DOI: 10.1038 / s41566-022-01083-y, DOI: 10.1002 / anie.202202380, demonstrating the high color purity and efficiency of these materials, which have great potential as next-generation green organic electroluminescent display materials. However, these boron-nitrogen material devices still suffer from drawbacks such as low efficiency and short lifespan. They need to be paired with suitable host materials to address issues such as electron-hole balance, carrier or exciton quenching, exciton energy transfer, and device stability, so as to effectively leverage the unique advantages of boron-nitrogen materials and meet the needs of commercial applications. Summary of the Invention
[0005] To address the above technical problems, the present invention provides a composition for a light-emitting layer and an organic electroluminescent device comprising the same. By using a composition for a light-emitting layer formed by a first host material, a second host material, and a double boron fluorescent material with a specific structure in the light-emitting layer of the organic electroluminescent device, the efficiency and lifespan of the device can be effectively improved.
[0006] The present invention provides the following technical solution: a composition for a light-emitting layer, comprising a first host material, a second host material, and a boron-containing fluorescent material, wherein the first host material is selected from the structure shown in general formula (A-1) or general formula (A-2):
[0007]
[0008] In general formulas (A-1) and (A-2), X represents an O atom, a S atom, or a N (-L4-Ar) atom. d );
[0009] L1, L2, L3, and L4 are independently represented as single bonds, substituted bonds, or unsubstituted C6-C6 bonds, respectively. 30 arylene, C2-C, substituted or unsubstituted 30 heteroaryl;
[0010] Ar a Ar b Ar c Ar d Each can be independently represented as either substituted or unsubstituted C3-C3. 10 Cycloalkyl, C3-C6 substituted or unsubstituted10 Heterocyclic alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0011] Ring A represents a benzene ring that is either substituted or unsubstituted;
[0012] R m R n R p R q Each occurrence is independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, C1-C10 alkyl group (substituted or unsubstituted), and C3-C6 alkyl group (substituted or unsubstituted). 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C1-C2 groups 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0013] i, j, s, and k are each independently represented as 0, 1, 2, 3, or 4;
[0014] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorinated alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;
[0015] In the structures shown in general formulas (A-1) and (A-2), any hydrogen atom may optionally be partially or completely replaced by deuterium;
[0016] The second main material is selected from the structure shown in general formula (B):
[0017]
[0018] In general formula (B), L5, L6, and L7 are each independently represented as single bonds, substituted by substituents, or unsubstituted C6 to C7 bonds, respectively. 30arylene, C2-C, substituted or unsubstituted 30 heteroaryl;
[0019] Ar e Ar f Ar g Each occurrence is independently represented as a hydrogen atom, or as a C3-C atom substituted or unsubstituted. 10 Cycloalkyl, C6-C6 substituted or unsubstituted 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0020] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorinated alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;
[0021] In the structure shown in general formula (B), any hydrogen atom may optionally be partially or completely replaced by deuterium;
[0022] Compounds excluded from general formula (B)
[0023] The boron-containing fluorescent material is selected from the structure shown in general formula (C-1) or general formula (C-2):
[0024]
[0025] In general formulas (C-1) and (C-2), the recurrence of Z being the same or different is represented by C-(R). o ); The R o Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the following: heteroaryl, C2-C30 borane alkyl group substituted or unsubstituted, and C3-C30 silane alkyl group substituted or unsubstituted;
[0026] Rings M1, M2, M3, and M4 represent C6-C6 rings substituted or unsubstituted with one or more R groups. 30 aryl group, C2-C2 substituted or unsubstituted by one or more R groups. 30 Heteroaryl, C6-C substituted or unsubstituted with one or more R groups 30 The aliphatic ring, C formed by the fusion of two or more aromatic rings, heteroaromatic rings, or aliphatic rings, substituted or unsubstituted with one or more Rs. 10 ~C 30 One type of fused ring;
[0027] Each occurrence of R, whether the same or different, represents a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the following: heteroaryl, C2-C30 borane alkyl group substituted or unsubstituted, and C3-C30 silane alkyl group substituted or unsubstituted;
[0028] The replacement of R is either a single bond or a parallel ring connection;
[0029] Ar1, Ar2, Ar3, Ar4, and Ar5 are independently represented as C1 to C5 groups, substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0030] X'1, X'2, X'3, and X'4 are independently represented as single bonds, -O-, -S-, and -N(R) bonds, respectively. d )-、-B(R e )-、-C(R f (R) g )-、-Si(R h (R) i - or -C(Rj)=C(R) k )-;
[0031] p, q, i, j represent 0 or 1;
[0032] And at least one of X'2, X'3, and X'4 exists and is represented as -B(R). e )-;
[0033] The R d R e R f R g R h R i R j R k Individually represented as C1 to C2 cells substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0034] The R f With R g Between, R h With R i Between, R d With adjacent R o Between, R e With adjacent R o Between, R d Between M1 and R e Between M1 and R d Between M2 and R e Between M2 and Ar1 and adjacent R o Between, between Ar1 and M3, between Ar2 and Ar3, and any adjacent R o The components between Ar5 and M4 are either not connected or are connected in a loop;
[0035] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C10 Alkyl or fluorine-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups;
[0036] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.
[0037] Furthermore, the R f With R g Between, R h With R i Between, R d With adjacent R o Between, R e With adjacent R o Between, R d Between M1 and R e Between M1 and R d Between M2 and R e Between M2 and Ar1 and adjacent R o Between, between Ar1 and M3, between Ar2 and Ar3, and any adjacent R o The bonds between Ar5 and M4 are not connected, or are connected in a ring through single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2)(R'3)-, -Si(R'4)(R'5)-, or -C(R'6)=C(R'7)-.
[0038] R'1, R'2, R'3, R'4, R'5, R'6, and R'7 are each independently represented as C1 to C2 groups that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0039] R'2 and R'3 are not connected or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene to form a ring.
[0040] R'4 and R'5 are not connected or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene to form a ring.
[0041] R'6 and R'7 are not connected or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene to form a ring.
[0042] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl or fluorine-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups;
[0043] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.
[0044] Furthermore, the first main material is selected from the structure shown in any one of general formulas (A-3) to (A-8):
[0045]
[0046] In general formulas (A-3) to (A-8), L1, L2, L3, and L4 are each independently represented as a single bond, substituted with a substituent, or unsubstituted C6 to C6 bonds, respectively. 30 arylene, C2-C, substituted or unsubstituted 30 heteroaryl;
[0047] The Ar a Ar b Ar c Ar d Each occurrence is independently represented as either substituted or unsubstituted C3-C3. 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0048] The R m R n Rp R q Each occurrence is independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C1-C2 groups 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0049] The i, j, s, and k are each independently represented as 0, 1, 2, 3, or 4;
[0050] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorinated alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;
[0051] In the structures shown in general formulas (A-3) to (A-8), any hydrogen atom may optionally be partially or completely replaced by deuterium; preferably, the first host material is selected from the structures shown in any one of general formulas (A-9) to (A-22).
[0052]
[0053]
[0054] In general formulas (A-9) to (A-22), L1, L2, L3, and L4 are each independently represented as single bonds, substituted with substituents, or unsubstituted C6 to C6 bonds, respectively. 30 arylene, C2-C, substituted or unsubstituted 30 heteroaryl;
[0055] The Ar a Ar b Ar c Ar dEach occurrence is independently represented as either substituted or unsubstituted C3-C3. 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0056] The R m R n R p R q Each occurrence is independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C1-C2 groups 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0057] The i, j, s, and k are each independently represented as 0, 1, 2, 3, or 4;
[0058] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorinated alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;
[0059] In the structures shown in general formulas (A-9) to (A-22), any hydrogen atom may optionally be partially or completely replaced by deuterium.
[0060] Furthermore, L1, L2, L3, and L4 are respectively independently represented as a single bond, a phenylene group substituted or unsubstituted with a substituent, a diphenylene group substituted or unsubstituted with a substituent, a terphenylene group substituted or unsubstituted with a substituent, a naphthylene group substituted or unsubstituted with a substituent, anthracene group substituted or unsubstituted with a substituent, a phenanthrene group substituted or unsubstituted with a substituent, a pyridylene group substituted or unsubstituted with a substituent, a quinolinylene group substituted or unsubstituted with a substituent, and a furan group substituted or unsubstituted with a substituent. , thiopheneyl group substituted or unsubstituted, benzofuranyl group substituted or unsubstituted, benzothiopheneyl group substituted or unsubstituted, dibenzofuranyl group substituted or unsubstituted, dibenzothiopheneyl group substituted or unsubstituted, carbazolyl group substituted or unsubstituted, 9,9-dimethylfluorenyl group substituted or unsubstituted, 9,9-diphenylfluorenyl group substituted or unsubstituted, spirofluorenyl group substituted or unsubstituted;
[0061] The R m R n R p R q Each of the following can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, methyl group (substituted or unsubstituted), ethyl group (substituted or unsubstituted), isopropyl group (substituted or unsubstituted), tert-butyl group (substituted or unsubstituted), cyclohexyl group (substituted or unsubstituted), cyclopentyl group (substituted or unsubstituted), adamantyl group (substituted or unsubstituted), phenyl group (substituted or unsubstituted), diphenyl group (substituted or unsubstituted), terphenyl group (substituted or unsubstituted), naphthyl group (substituted or unsubstituted), anthracene group (substituted or unsubstituted), phenanthryl group (substituted or unsubstituted), pyridyl group (substituted or unsubstituted), quinolinyl group (substituted or unsubstituted), and furfural group (substituted or unsubstituted). alkyl, thiophene group substituted or unsubstituted, benzofuran group substituted or unsubstituted, benzothiophene group substituted or unsubstituted, dibenzofuran group substituted or unsubstituted, dibenzothiophene group substituted or unsubstituted, carbazolyl group substituted or unsubstituted, 9,9-dimethylfluorenyl group substituted or unsubstituted, 9,9-diphenylfluorenyl group substituted or unsubstituted, spirofluorenyl group substituted or unsubstituted, triazine group substituted or unsubstituted, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group substituted or unsubstituted, diphenylamino group substituted or unsubstituted, indole group substituted or unsubstituted, benzoindole group substituted or unsubstituted;
[0062] The Ar a Ar bAr c Ar d Individually represented as methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), cyclopentyl (substituted or unsubstituted), adamantyl (substituted or unsubstituted), phenyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraceneyl (substituted or unsubstituted), phenanthrene (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), furfural (substituted or unsubstituted). alkyl, thiophene group substituted or unsubstituted, benzofuran group substituted or unsubstituted, benzothiophene group substituted or unsubstituted, dibenzofuran group substituted or unsubstituted, dibenzothiophene group substituted or unsubstituted, carbazolyl group substituted or unsubstituted, 9,9-dimethylfluorenyl group substituted or unsubstituted, 9,9-diphenylfluorenyl group substituted or unsubstituted, spirofluorenyl group substituted or unsubstituted, triazine group substituted or unsubstituted, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group substituted or unsubstituted, indolyl group substituted or unsubstituted, benzoindolyl group substituted or unsubstituted;
[0063] The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, azirphenanthreneyl, and 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl.
[0064] Furthermore, the first main material is selected from the structure shown below:
[0065]
[0066]
[0067]
[0068]
[0069] Furthermore, the second main material is selected from the structure shown in any one of general formulas (B-1) to (B-4):
[0070]
[0071] In general formulas (B-1) to (B-4), X' represents an O atom, a S atom, or a N (-L8-Ar atom). h ) or C(Rv)(Rz);
[0072] "X" represents an O atom, an S atom, an N-ph, a dimethyl-substituted methylene or a diphenyl-substituted methylene;
[0073] L5, L6, L7, and L8 are independently represented as single bonds, C6 to C8 bonds substituted with substituents, or C6 to C8 bonds that are unsubstituted, respectively. 30 arylene, C2-C, substituted or unsubstituted 30 heteroaryl;
[0074] The Ar f Ar g Ar h Each of the C3 to C3 atoms can be represented independently as a hydrogen atom, substituted or unsubstituted. 10 Cycloalkyl, C6-C6 substituted or unsubstituted 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0075] Ring B represents a benzene ring that is either substituted or unsubstituted;
[0076] Ra, R b Each can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C1-C2 groups 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0077] g and h can be independently represented as 0, 1, 2, 3 or 4 respectively;
[0078] Each occurrence of Rv and Rz independently represents either a C1-C1 column substituted with or unsubstituted with a substituent. 10 Alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0079] Rv and Rz are not connected or are connected via a single key;
[0080] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorinated alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;
[0081] In the structures shown in general formulas (B-1) to (B-4), any hydrogen atom may optionally be partially or completely replaced by deuterium;
[0082] Compounds excluded from general formula (B-4)
[0083] Preferably, the second main material is selected from the structure shown in any one of general formulas (B-5) to (B-10):
[0084]
[0085] In general formulas (B-5) to (B-10), X' represents an O atom, a S atom, or a N (-L8-Ar atom). h ) or C(Rv)(Rz);
[0086] L5, L6, L7, and L8 are independently represented as single bonds, C6 to C8 bonds substituted with substituents, or C6 to C8 bonds that are unsubstituted, respectively. 30 arylene, C2-C, substituted or unsubstituted 30 heteroaryl;
[0087] The Ar f Ar g Ar h Each of the C3 to C3 atoms can be represented independently as a hydrogen atom, substituted or unsubstituted. 10 Cycloalkyl, C6-C6 substituted or unsubstituted 30 Aryl, substituted or unsubstituted C2-C30 One of the heteroaryl groups;
[0088] R a R b Each can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C1-C2 groups 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0089] g and h can be independently represented as 0, 1, 2, 3 or 4 respectively;
[0090] Each occurrence of Rv and Rz independently represents either a C1-C1 column substituted with or unsubstituted with a substituent. 10 Alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0091] Rv and Rz are not connected or are connected via a single key;
[0092] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorinated alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;
[0093] In the structures shown in general formulas (B-5) to (B-10), any hydrogen atom may optionally be partially or completely replaced by deuterium;
[0094] Preferably, the second body material is selected from the structure shown in any one of general formulas (B-11) to (B-16):
[0095]
[0096] In general formulas (B-11) to (B-16), L5, L6, L7, and L8 are independently represented as single bonds, C6 to C8 bonds substituted with substituents, or C6 to C8 bonds that are unsubstituted. 30 arylene, C2-C, substituted or unsubstituted 30 heteroaryl;
[0097] The Ar f Ar g Ar h Each of the C3 to C3 atoms can be represented independently as a hydrogen atom, substituted or unsubstituted. 10 Cycloalkyl, C6-C6 substituted or unsubstituted 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0098] R a R b Each can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C1-C2 groups 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0099] g and h can be independently represented as 0, 1, 2, 3 or 4 respectively;
[0100] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorinated alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;
[0101] In the structures shown in formulas (B-11) to (B-16), any hydrogen atom may optionally be partially or completely replaced by deuterium.
[0102] Furthermore, L5, L6, L7, and L8 are respectively independently represented as a single bond, a phenylene group substituted or unsubstituted with a substituent, a diphenylene group substituted or unsubstituted with a substituent, a terphenylene group substituted or unsubstituted with a substituent, a naphthylene group substituted or unsubstituted with a substituent, anthracene group substituted or unsubstituted with a substituent, a phenanthrene group substituted or unsubstituted with a substituent, a pyridylene group substituted or unsubstituted with a substituent, a quinolinylene group substituted or unsubstituted with a substituent, and a furan group substituted or unsubstituted with a substituent. , thiopheneyl group substituted or unsubstituted, benzofuranyl group substituted or unsubstituted, benzothiopheneyl group substituted or unsubstituted, dibenzofuranyl group substituted or unsubstituted, dibenzothiopheneyl group substituted or unsubstituted, carbazolyl group substituted or unsubstituted, 9,9-dimethylfluorenyl group substituted or unsubstituted, 9,9-diphenylfluorenyl group substituted or unsubstituted, spirofluorenyl group substituted or unsubstituted;
[0103] The R a R b Each of the following can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, methyl group (substituted or unsubstituted), ethyl group (substituted or unsubstituted), isopropyl group (substituted or unsubstituted), tert-butyl group (substituted or unsubstituted), cyclohexyl group (substituted or unsubstituted), cyclopentyl group (substituted or unsubstituted), adamantyl group (substituted or unsubstituted), phenyl group (substituted or unsubstituted), diphenyl group (substituted or unsubstituted), terphenyl group (substituted or unsubstituted), naphthyl group (substituted or unsubstituted), anthracene group (substituted or unsubstituted), phenanthryl group (substituted or unsubstituted), pyridyl group (substituted or unsubstituted), quinolinyl group (substituted or unsubstituted), and furfural group (substituted or unsubstituted). alkyl, thiophene group substituted or unsubstituted, benzofuran group substituted or unsubstituted, benzothiophene group substituted or unsubstituted, dibenzofuran group substituted or unsubstituted, dibenzothiophene group substituted or unsubstituted, carbazolyl group substituted or unsubstituted, 9,9-dimethylfluorenyl group substituted or unsubstituted, 9,9-diphenylfluorenyl group substituted or unsubstituted, spirofluorenyl group substituted or unsubstituted, triazine group substituted or unsubstituted, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group substituted or unsubstituted, diphenylamino group substituted or unsubstituted, indole group substituted or unsubstituted, benzoindole group substituted or unsubstituted;
[0104] The Ar f Ar g Ar hRv and Rz represent, independently, methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), cyclopentyl (substituted or unsubstituted), adamantyl (substituted or unsubstituted), phenyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraceneyl (substituted or unsubstituted), phenanthrene (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), and [other compounds, substituted or unsubstituted]. Substituted furanyl, thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), benzothiopheneyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiopheneyl (substituted or unsubstituted), carbazolyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), 9,9-diphenylfluorenyl (substituted or unsubstituted), spirofluorenyl (substituted or unsubstituted), triazine (substituted or unsubstituted), 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl (substituted or unsubstituted), indolyl (substituted or unsubstituted), benzoindolyl (substituted or unsubstituted).
[0105] The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, azirphenanthreneyl, and 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl.
[0106] Furthermore, the second main material is selected from the structure shown below:
[0107]
[0108]
[0109]
[0110] Any one of them.
[0111] Furthermore, the boron-containing fluorescent material is selected from any one of general formulas (C-3) to (C-7):
[0112]
[0113] In general formulas (C-3) to (C-7), the meanings of Z, Ar1, Ar2, Ar3, Ar4, Ar5, and M1 are the same as those defined above;
[0114] Z1, Z2, Z3, Z4, Z5, Z6, and Z7 are independently represented as C-(R1), C-(R2), C-(R3), C-(R4), C-(R5), C-(R6), and C-(R7);
[0115] R1, R2, R3, R4, R5, R6, and R7 are independently represented as a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, and C1-C1 atoms substituted or unsubstituted with substituents, respectively. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the following: heteroaryl, C2-C30 borane alkyl group substituted or unsubstituted, and C3-C30 silane alkyl group substituted or unsubstituted;
[0116] Ar1 and R3 are either not connected or connected in a loop;
[0117] Ar1 and R4 are either not connected or connected in a loop;
[0118] Ar1 and R5 are either not connected or connected in a loop;
[0119] The Ar2 and Ar3 rings are either not connected or connected to form a ring;
[0120] R6 and R7 are either not connected or connected in a loop;
[0121] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl or fluorine-substituted C1-C 10 Alkyl, C3-C10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups;
[0122] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.
[0123] Furthermore, Ar1 and R3 are not connected or are connected in a ring by single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2)(R'3)-, -Si(R'4)(R'5)- or -C(R'6)=C(R'7)-;
[0124] Ar1 and R4 are not connected or are connected in a ring by single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2)(R'3)-, -Si(R'4)(R'5)- or -C(R'6)=C(R'7)-;
[0125] Ar1 and R5 are not connected or are connected in a ring by single bond, double bond, -O-, -S-, -N(R'1)-, -C(R'2)(R'3)-, -Si(R'4)(R'5)- or -C(R'6)=C(R'7)-;
[0126] Ar1 and R6 are not connected or are connected in a ring by single bond, double bond, -O-, -S-, -N(R'1)-, -C(R'2)(R'3)-, -Si(R'4)(R'5)- or -C(R'6)=C(R'7)-;
[0127] The Ar2 and Ar3 rings are not connected or are connected to form a ring by single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2)(R'3)-, -Si(R'4)(R'5)- or -C(R'6)=C(R'7)-;
[0128] R6 and R7 are not connected or are connected in a ring by a single bond, double bond, -O-, -S-, -N(R'1)-, -C(R'2)(R'3)-, -Si(R'4)(R'5)- or -C(R'6)=C(R'7)-;
[0129] R'1, R'2, R'3, R'4, R'5, R'6, and R'7 are each independently represented as C1 to C2 groups that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0130] R'2 and R'3 are not connected or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene to form a ring.
[0131] R'4 and R'5 are not connected or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene to form a ring.
[0132] R'6 and R'7 are not connected or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene to form a ring.
[0133] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl or fluorine-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups;
[0134] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.
[0135] Preferably, the boron-containing fluorescent material is selected from the structure shown in any one of general formulas (D-1) to (D-23):
[0136]
[0137]
[0138]
[0139]
[0140] In general formulas (D-1) to (D-23), Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and Ar7 are independently represented as C1 to C7 groups, substituted or unsubstituted.10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0141] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 Each of the following can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the following: heteroaryl, C2-C30 borane alkyl group substituted or unsubstituted, and C3-C30 silane alkyl group substituted or unsubstituted;
[0142] m1, m2, m3, m4, m5, m6, m7, m8, m9, m 10 m 11 m 12 Represented as 0 to the maximum allowed number of substitutions;
[0143] X'4 represents a single bond, -O-, -S-, -N(R) d )-、-B(R e )-、-C(R f (R) g )-、-Si(R h (R) i - or -C(Rj)=C(R) k )-;
[0144] q represents 0 or 1;
[0145] The R d R e R f R g Rh R i R j R k Individually represented as C1 to C2 cells substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0146] The R f With R g Between, R h With R i They are either not connected or connected in a loop;
[0147] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl or fluorine-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups;
[0148] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B;
[0149] Preferably, the boron-containing fluorescent material is selected from any one of general formulas (E-1) to (E-23):
[0150]
[0151]
[0152]
[0153]
[0154] In general formulas (E-1) to (E-23), Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and Ar7 are independently represented as C1 to C7 groups, substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0155] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 Each of the following can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the following: heteroaryl, C2-C30 borane alkyl group substituted or unsubstituted, and C3-C30 silane alkyl group substituted or unsubstituted;
[0156] X'4 represents a single bond, -O-, -S-, -N(R) d )-、-B(R e )-、-C(R f (R) g )-、-Si(R h (R) i - or -C(Rj)=C(R) k )-;
[0157] q represents 0 or 1;
[0158] The R d R e R f R g R h R i R j R k Individually represented as C1 to C2 cells substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;
[0159] The R f With R g Between, R h With R i They are either not connected or connected in a loop;
[0160] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl or fluorine-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups;
[0161] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.
[0162] Furthermore, Ro, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12Represented as hydrogen atom, deuterium atom, halogen atom, cyano group, methyl group (substituted or unsubstituted), ethyl group (substituted or unsubstituted), isopropyl group (substituted or unsubstituted), tert-butyl group (substituted or unsubstituted), cyclohexyl group (substituted or unsubstituted), cyclopentyl group (substituted or unsubstituted), adamantyl group (substituted or unsubstituted), phenyl group (substituted or unsubstituted), diphenyl group (substituted or unsubstituted), terphenyl group (substituted or unsubstituted), naphthyl group (substituted or unsubstituted), anthracene group (substituted or unsubstituted), phenanthryl group (substituted or unsubstituted), pyridyl group (substituted or unsubstituted), quinolinyl group (substituted or unsubstituted), furanyl group (substituted or unsubstituted). Thiophene group substituted or unsubstituted, benzofuran group substituted or unsubstituted, benzothiophene group substituted or unsubstituted, dibenzofuran group substituted or unsubstituted, dibenzothiophene group substituted or unsubstituted, carbazolyl group substituted or unsubstituted, 9,9-dimethylfluorenyl group substituted or unsubstituted, 9,9-diphenylfluorenyl group substituted or unsubstituted, spirofluorenyl group substituted or unsubstituted, triazine group substituted or unsubstituted, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group substituted or unsubstituted, diphenylamino group substituted or unsubstituted, indole group substituted or unsubstituted, benzoindole group substituted or unsubstituted;
[0163] The M1, M2, M3, and M4 rings represent any one of the following groups substituted or unsubstituted by one or more R groups: phenyl, naphthyl, anthracene, phenanthryl, pyridinyl, quinolinyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, indole[3,2,1-jk]carbazoyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and spirofluorenyl.
[0164] R represents a deuterium atom, a halogen atom, a cyano group, a methyl group (substituted or unsubstituted), an ethyl group (substituted or unsubstituted), an isopropyl group (substituted or unsubstituted), a tert-butyl group (substituted or unsubstituted), a cyclohexyl group (substituted or unsubstituted), a cyclopentyl group (substituted or unsubstituted), an adamantyl group (substituted or unsubstituted), a phenyl group (substituted or unsubstituted), a diphenyl group (substituted or unsubstituted), a terphenyl group (substituted or unsubstituted), a naphthyl group (substituted or unsubstituted), anthracene group (substituted or unsubstituted), a phenanthryl group (substituted or unsubstituted), a pyridyl group (substituted or unsubstituted), a quinolinyl group (substituted or unsubstituted), or a furanyl group (substituted or unsubstituted). Thiophene group substituted or unsubstituted, benzofuran group substituted or unsubstituted, benzothiophene group substituted or unsubstituted, dibenzofuran group substituted or unsubstituted, dibenzothiophene group substituted or unsubstituted, carbazolyl group substituted or unsubstituted, 9,9-dimethylfluorenyl group substituted or unsubstituted, 9,9-diphenylfluorenyl group substituted or unsubstituted, spirofluorenyl group substituted or unsubstituted, triazine group substituted or unsubstituted, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group substituted or unsubstituted, diphenylamino group substituted or unsubstituted, indole group substituted or unsubstituted, benzoindole group substituted or unsubstituted;
[0165] Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and Ar7 represent cyclohexyl (substituted or unsubstituted), cyclopentyl (substituted or unsubstituted), adamantyl (substituted or unsubstituted), phenyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraceneyl (substituted or unsubstituted), phenanthryl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), and others (substituted or unsubstituted). Unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenylyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzoindolyl;
[0166] The R d R e R f R g R h R i R j R kThis is represented as methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), cyclopentyl (substituted or unsubstituted), adamantyl (substituted or unsubstituted), phenyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraceneyl (substituted or unsubstituted), phenanthrene (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), and so on. Substituted thiophene group, benzofuran group substituted or unsubstituted, benzothiophene group substituted or unsubstituted, dibenzofuran group substituted or unsubstituted, dibenzothiophene group substituted or unsubstituted, carbazolyl group substituted or unsubstituted, 9,9-dimethylfluorenyl group substituted or unsubstituted, 9,9-diphenylfluorenyl group substituted or unsubstituted, spirofluorenyl group substituted or unsubstituted, triazine group substituted or unsubstituted, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group substituted or unsubstituted, diphenylamino group substituted or unsubstituted, indole group substituted or unsubstituted, benzoindole group substituted or unsubstituted;
[0167] The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, azirphenanthrenel, diphenylamino, and 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl.
[0168] Furthermore, the boron-containing fluorescent material is selected from the following specific structures:
[0169]
[0170]
[0171]
[0172]
[0173]
[0174]
[0175] Any one of them.
[0176] Furthermore, the first main material is a hole-type main material, and the second main material is an electronic-type main material.
[0177] Furthermore, it also includes a sensitizing material, wherein the sensitizing material is a phosphorescent sensitizing material or a TADF sensitizing material;
[0178] Preferably, the phosphorus photosensitive material is a metal complex containing iridium or platinum.
[0179] The present invention also provides an organic electroluminescent device, comprising, in sequence, a substrate, a first electrode, an organic functional layer, and a second electrode, wherein the organic functional layer is located between the first electrode and the second electrode, and the organic functional layer comprises the composition for the light-emitting layer.
[0180] Furthermore, the organic functional layer includes at least one light-emitting layer, and the light-emitting layer includes a composition for the light-emitting layer;
[0181] Furthermore, the organic functional layer includes a hole transport region, a light-emitting layer, and an electron transport region, wherein the light-emitting layer comprises a composition for the light-emitting layer.
[0182] Furthermore, the hole transport region includes a hole injection layer and a hole transport layer.
[0183] Furthermore, the hole transport region includes a hole injection layer, a hole transport layer, and an electron blocking layer.
[0184] Furthermore, the electron transport region includes an electron transport layer and an electron injection layer.
[0185] Furthermore, the electron transport region includes a hole blocking layer, an electron transport layer, and an electron injection layer.
[0186] Compared with the prior art, the beneficial technical effects of the present invention are as follows: The composition for the light-emitting layer provided by the present invention is composed of a first host material, a second host material and a boron-containing fluorescent material. The first host material has a suitable hole mobility, and the second host material has a suitable electron mobility, which helps to achieve a good electron-hole balance in the device, broaden the exciton recombination region and suppress the exciton quenching problem. At the same time, it can efficiently transfer exciton energy to the boron-containing fluorescent material. When applied to the light-emitting layer of organic electroluminescent devices, it improves efficiency and lifetime while giving full play to the high color purity advantage of the boron-containing fluorescent material. Attached Figure Description
[0187] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device of the present invention;
[0188] Wherein, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer. Detailed Implementation
[0189] The principles and features of the present invention are described below with reference to the accompanying drawings and embodiments. The examples given are only for explaining the present invention and are not intended to limit the scope of the present invention.
[0190] In the accompanying drawings, for clarity, the dimensions of layers and regions may be exaggerated. It will also be understood that when a layer or element is referred to as being "above" another layer or substrate, the layer or element may be directly above that other layer or substrate, or intermediate layers may be present. Furthermore, it will be understood that when a layer is referred to as being "between" two layers, the layer may be the only layer between the two layers, or one or more intermediate layers may be present. The same reference numerals throughout the drawings denote the same elements.
[0191] In this invention, the terms "upper," "lower," "top," and "bottom," used to describe electrodes, organic electroluminescent devices, and other structures, indicate orientation only in a specific state and do not imply that the structure can only exist in that orientation. Conversely, if the structure can be repositioned, such as by inverting it, the orientation of the structure changes accordingly. Specifically, in this invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode closer to the substrate during fabrication, while the opposite side farther from the substrate is the "top" or "upper" side.
[0192] In this invention, the substituted or unsubstituted aromatic amino group referred to in this invention means... Wherein Q1 and Q2 represent aromatic groups that are substituted or unsubstituted, and Q1 and Q2 preferably represent C6-C6 groups that are substituted or unsubstituted. 30 The aryl group may be substituted or unsubstituted at C2-C2. 30 Mixed aromatic compounds.
[0193] In this invention, the C3-C3 groups described herein are substituted or unsubstituted. 30 Silyl refers to Where Q3, Q4, and Q5 represent C1 to C2. 10 Alkyl, C3-C 10 Cycloalkyl.
[0194] In this invention, the C2-C1 groups described herein are substituted or unsubstituted. 30 Boronyl refers to Where Q6 and Q7 represent C1-C 10 Alkyl, C3-C 10 Cycloalkyl.
[0195] In this invention, C6 to C6 are substituted or unsubstituted. 30 Aryl refers to an aryl group with 6 to 30 carbon atoms, substituted or unsubstituted, preferably an aryl group with 6 to 20 carbon atoms, preferably an aryl group with 6 to 18 carbon atoms, preferably an aryl group with 6 to 10 carbon atoms, preferably substituted or unsubstituted phenyl, naphthyl, anthracene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, phenanthyl, fused tetraphenyl, pyrene, diphenyl, terphenyl, etc. The following are examples of compounds: triphenylene, perylene, indene, and 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, but not limited to these.
[0196] In this invention, C6~C 30 Aryl refers to an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, and more preferably an aryl group having 6 to 10 carbon atoms. Other preferred aryl groups include phenyl, naphthyl, anthraceneyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, phenanthryl, tetraphenyl, pyrene, diphenyl, and terphenyl. The compounds include, but are not limited to, triphenyl, peryl, indole, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl.
[0197] In this invention, deuterium-substituted C6-C 30 The aryl group refers to a deuterated aryl group with 6 to 30 carbon atoms, preferably a deuterated aryl group with 6 to 20 carbon atoms, preferably a deuterated aryl group with 6 to 18 carbon atoms, preferably a deuterated aryl group with 6 to 10 carbon atoms, and preferably a deuterated phenyl, deuterated naphthyl, deuterated anthracene, deuterated fluorenyl, deuterated dimethylfluorenyl, deuterated diphenylfluorenyl, deuterated spirofluorenyl, deuterated phenanthrene, deuterated tetraphenyl, deuterated pyrene, deuterated diphenyl, deuterated terphenyl, and deuterated... The compounds include, but are not limited to, deuterated triphenyl, deuterated peryl, deuterated indyl, and deuterated 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl.
[0198] In this invention, C2 to C3 are substituted or unsubstituted. 30 A heteroaryl group refers to a heteroaryl group having 2 to 30 carbon atoms, either substituted or unsubstituted, preferably a heteroaryl group having 2 to 20 carbon atoms, preferably a heteroaryl group having 4 to 20 carbon atoms, preferably a heteroaryl group having 4 to 10 carbon atoms, preferably a heteroaryl group having 5 to 10 carbon atoms, preferably a heteroaryl group having 6 to 12 carbon atoms, and preferably a furan with substituted or unsubstituted carbon atoms. Thiophene group (substituted or unsubstituted), pyrrole group (substituted or unsubstituted), pyrazol group (substituted or unsubstituted), imidazo group (substituted or unsubstituted), triazol group (substituted or unsubstituted), oxazol group (substituted or unsubstituted), thiazolyl group (substituted or unsubstituted), oxadiazol group (substituted or unsubstituted), thiadiazol group (substituted or unsubstituted), pyridinyl group (substituted or unsubstituted), pyrimidinyl group (substituted or unsubstituted), pyrazine group (substituted or unsubstituted). Triazine group (substituted or unsubstituted), benzofuran group (substituted or unsubstituted), benzothiophene group (substituted or unsubstituted), benzimidazolyl group (substituted or unsubstituted), indolyl group (substituted or unsubstituted), quinolinyl group (substituted or unsubstituted), isoquinolinyl group (substituted or unsubstituted), quinazolinyl group (substituted or unsubstituted), quinolinyl group (substituted or unsubstituted), naphthidyl group (substituted or unsubstituted), benzoxazine group (substituted or unsubstituted), and others. The following are examples of substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted benzinyl, substituted or unsubstituted benzithiazinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted benzoindolyl, but not limited to these.
[0199] In this invention, C2~C 30The heteroaryl group refers to a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 20 carbon atoms, more preferably a heteroaryl group having 4 to 20 carbon atoms, more preferably a heteroaryl group having 4 to 10 carbon atoms, more preferably a heteroaryl group having 6 to 12 carbon atoms, and preferably furanyl, thiophene, pyrrole, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, or pyrimidinyl. Pyrazinyl, triazinyl, benzofuranyl, benzothiophenyl, benzoimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinolinyl, naphridinyl, benzooxazinyl, benzothiazinyl, acridineyl, benazinoyl, benazinoyl, benazinoyl, benazinoyl, fumonyl, dibenzofuranyl, dibenzothiaphenyl, carbazolyl, N-phenylcarbazolyl substituted or unsubstituted, benzoindolyl, but not limited to these.
[0200] In this invention, deuterium-substituted C2-C 30 The heteroaryl group refers to a heteroaryl group with 5 to 30 deuterated carbon atoms, preferably a heteroaryl group with 5 to 20 deuterated carbon atoms, preferably a heteroaryl group with 5 to 10 deuterated carbon atoms, preferably a heteroaryl group with 6 to 12 deuterated carbon atoms, preferably deuterated furanyl, deuterated thiophene, deuterated pyrrole, deuterated pyrazolyl, deuterated imidazolyl, deuterated triazolyl, deuterated oxazolyl, deuterated thiazolyl, deuterated oxadiazolyl, deuterated thiadiazolyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated triazine, and deuterated... Substituted benzofuranyl, deuterated benzothiophenyl, deuterated benzimidazolyl, deuterated indolyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated quinazolinyl, deuterated quinolinyl, deuterated naphthidyl, deuterated benzoxazinyl, deuterated benzothiazinyl, deuterated acridineyl, deuterated benzazinyl, deuterated benzthiazinyl, deuterated benzoxazinyl, deuterated fumonyl, deuterated dibenzofuranyl, deuterated dibenzothiaphenyl, deuterated carbazoyl, deuterated substituted N-phenylcarbazoyl, deuterated benzoindolyl, but not limited to these.
[0201] In this invention, the number of heteroatoms in the heteroaryl group is 1-5, preferably 1-4, preferably 1-3, preferably 1-2, and preferably 1.
[0202] The C1-C1 components of this invention, whether substituted or unsubstituted, are... 10Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to an alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted, preferably an alkyl group having 1 to 5 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, etc., substituted or unsubstituted. Substituted isobutyl, sec-butyl substituted or unsubstituted, neopentyl substituted or unsubstituted, n-pentyl substituted or unsubstituted, isopentyl substituted or unsubstituted, octyl substituted or unsubstituted, heptyl substituted or unsubstituted, n-decyl substituted or unsubstituted, 1-methylpentyl substituted or unsubstituted, 2-methylpentyl substituted or unsubstituted, 3-methylpentyl substituted or unsubstituted, 1-butylpentyl substituted or unsubstituted, etc., but not limited to these.
[0203] The C1 to C of this invention 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, etc., but not limited to these.
[0204] The deuterium-substituted C1-C of the present invention 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to a deuterated alkyl group having 1 to 10 carbon atoms, preferably a deuterated alkyl group having 1 to 5 carbon atoms, preferably a deuterated alkyl group having 1 to 4 carbon atoms, preferably deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, deuterated tert-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated neopentyl, deuterated n-pentyl, deuterated isopentyl, deuterated octyl, deuterated heptyl, deuterated n-decyl, deuterated 1-methylpentyl, deuterated 2-methylpentyl, deuterated 3-methylpentyl, deuterated 1-butylpentyl, etc., but not limited to these.
[0205] The C3-C3 groups described in this invention, whether substituted or unsubstituted, are... 10The cycloalkyl group preferably uses C4-C9 cycloalkyl groups that are substituted or unsubstituted, more preferably C5-C8 cycloalkyl groups that are substituted or unsubstituted, and particularly preferably C5-C7 cycloalkyl groups that are substituted or unsubstituted. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.
[0206] The C3~C of this invention 10 The cycloalkyl group is preferably C4-C9 cycloalkyl, more preferably C5-C8 cycloalkyl, and particularly preferably C5-C7 cycloalkyl. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.
[0207] The deuterium-substituted C3-C of the present invention 10 The cycloalkyl group is preferably a deuterated C4-C9 cycloalkyl group, more preferably a deuterated C5-C8 cycloalkyl group, and particularly preferably a deuterated C5-C7 cycloalkyl group. Non-limiting examples may include, but are not limited to, deuterated cyclopropyl, deuterated cyclobutyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated 4-methylcyclohexyl, deuterated 4,4-dimethylcyclohexyl, deuterated adamantyl, and deuterated cycloheptyl.
[0208] The halogen atom mentioned in this invention refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
[0209] The C2 to C of this invention 10 Alkenyl refers to vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1,1-dimethylallyl, 1-methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, and 3-phenyl-1-butenyl, etc., but is not limited to these.
[0210] In this invention, the substituents used for the substituent groups are selected from one or more of the following: deuterium, cyano, adamantyl, methyl, ethyl, n-propyl, isopropyl, tert-amyl, tert-butyl, n-butyl, isobutyl, sec-butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, furanyl, thiophene, indolyl, pyrrole, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, spirofluorenyl, carbazole, N-phenylcarbazole, diphenylamino, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, and deuterated tert-butyl.
[0211] The organic electroluminescent device of the present invention can be a bottom-emitting organic electroluminescent device, a top-emitting organic electroluminescent device, or a multilayer organic electroluminescent device, and there is no specific limitation thereto.
[0212] The organic electroluminescent device of the present invention includes a substrate, a first electrode, an organic functional layer, and a second electrode. The organic functional layer may include a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region may include a hole injection layer, a hole transport layer, and an electron blocking layer. The electron transport region may include a hole blocking layer, an electron transport layer, and an electron injection layer. Additionally, a CPL layer may be disposed on the second electrode.
[0213] As the substrate for the organic electroluminescent device of this invention, any substrate commonly used in organic electroluminescent devices can be used. Examples include transparent substrates, such as glass or transparent PI film substrates; and opaque substrates, such as silicon substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Their application varies depending on their properties. In this invention, a transparent PI film substrate is preferred. There are no particular limitations on the thickness of the substrate.
[0214] A first electrode is formed on a substrate, and the first electrode and a second electrode may be opposite each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include metals such as Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, or Cr, or it may be an alloy of several metals, or a combination of metals, metal oxides, or metal alloys. The thickness of the first electrode layer depends on the material used, and is typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.
[0215] The organic functional layer disposed between the first electrode and the second electrode may, from bottom to top, include a hole transport region, a light-emitting layer, and an electron transport region.
[0216] In this invention, the hole transport region constituting the organic electroluminescent device can be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, etc.
[0217] As for the materials used in the hole injection layer, hole transport layer, and electron blocking layer, any material can be selected from known materials used in organic electroluminescent devices.
[0218] The hole injection layer comprises a host organic material capable of conducting holes, and a p-type doped material with a deep HOMO level (correspondingly, a deep LUMO level). Based on empirical observations, to achieve smooth hole injection from the anode to the organic film, the HOMO level of the host organic material used in the anode interface buffer layer must possess certain characteristics with the p-doped material. This is necessary to enable charge transfer states between the host and doped materials, achieve ohmic contact between the buffer layer and the anode, and realize efficient hole injection conduction from the electrode to the hole injection layer.
[0219] Based on the above empirical summary, for hole-based host organic materials with different HOMO energy levels, it is necessary to select different P-doped materials to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.
[0220] Preferably, the main organic material used as the hole injection layer of the present invention may be selected from the following compounds disclosed in the prior art: JP1996048656A, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN105439999A or CN103108859A.
[0221] Preferably, the p-type doped material is a charge-conducting compound disclosed in the prior art. The p-type dopant can be selected from compounds disclosed in any of the following documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2045848A1, DE10200703122. 0A1, US20100181555A1, US20100102709A1, WO2009003455A1, WO2010094378A1, WO2011120709A1, US20100096600A1, DE102012209523A1, CN101728485A and WO2012095143A1, but not limited to these.
[0222] In the hole injection layer of the present invention, the ratio of hole transport material to P-type doped material is 99:1-95:5, preferably 99:1-97:3, based on mass meter.
[0223] The thickness of the hole injection layer of the present invention can be 5-100 nm, preferably 5-50 nm, and more preferably 5-20 nm, but the thickness is not limited to this range.
[0224] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:
[0225]
[0226]
[0227] Preferably, the main organic material used as the hole transport layer material and the hole injection layer of the present invention is selected from the same compound.
[0228] The thickness of the hole transport layer of the present invention can be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.
[0229] In one embodiment of the present invention, the electron blocking layer material may be selected from the compounds disclosed in the prior art:
[0230]
[0231] The thickness of the electron blocking layer of the present invention can be 1-50 nm, preferably 5-40 nm, but the thickness is not limited to this range.
[0232] After forming the hole injection layer, hole transport layer, and electron blocking layer, a corresponding light-emitting layer is formed on top of the electron blocking layer.
[0233] The luminescent layer may include a first host material, a second host material, and a boron-containing fluorescent material. The first host material is selected from the structure shown in general formula (A-1) or general formula (A-2), the second host material is selected from the structure shown in general formula (B), and the boron-containing fluorescent material is selected from the structure shown in general formula (C-1) or general formula (C-2).
[0234] The contents of the first main material, the second main material, and the double boron fluorescent material can be determined based on existing technology or through simple experiments.
[0235] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.
[0236] The main material comprises a first main material and a second main material, wherein the mass ratio of the first main material and the second main material is 1:4 to 1:1, preferably 1:3 to 3:1, preferably 1:2 to 2:1, and preferably 2:3 to 3:2.
[0237] The thickness of the light-emitting layer can be adjusted to optimize luminous efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and even more preferably 15-40 nm, but the thickness is not limited to this range.
[0238] In this invention, the electron transport region may include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed on the light-emitting layer, but is not limited thereto.
[0239] A hole-blocking layer is a layer that prevents holes injected from the anode from penetrating the light-emitting layer and entering the cathode, thereby extending the device's lifetime and improving its performance. The hole-blocking layer of this invention can be disposed on top of the light-emitting layer. As the hole-blocking layer material for the organic electroluminescent device of this invention, compounds with hole-blocking properties known in the prior art can be used, for example:
[0240]
[0241]
[0242] The thickness of the hole blocking layer of the present invention can be 2-200nm, preferably 5-150nm, more preferably 5-50nm, but the thickness is not limited to this range.
[0243] An electron transport layer may be disposed above the light-emitting layer or (if present) a hole-blocking layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers these received electrons to the light-emitting layer. Preferably, a material with high electron mobility is used. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials disclosed in the prior art for organic electroluminescent devices can be used, for example:
[0244]
[0245] In a preferred embodiment of the invention, the electron transport layer further includes other compounds conventionally used in electron transport layers, such as Alq3, Liq, preferably Liq.
[0246] The thickness of the electron transport layer of the present invention can be 10-80 nm, preferably 20-60 nm and more preferably 25-45 nm, but the thickness is not limited to this range.
[0247] An electron injection layer may be disposed above the electron transport layer. The electron injection layer material is typically preferably a material with a low work function, which facilitates electron injection into the organic functional material layer. As the electron injection layer material for the organic electroluminescent device of the present invention, electron injection layer materials for organic electroluminescent devices disclosed in the prior art can be used, for example:
[0248]
[0249]
[0250] The thickness of the electron injection layer of the present invention can be 0.1-5 nm, preferably 0.5-3 nm and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.
[0251] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmission electrode, a semi-transmission electrode, or a reflection electrode. When the second electrode is a transmission electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF2, Ba, Ag, or compounds or mixtures thereof; when the second electrode is a semi-transmission electrode or a reflection electrode, it may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or compounds or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.
[0252] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer.
[0253] The method for preparing the organic electroluminescent device of the present invention includes sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, onto a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI can be used, but are not limited thereto. In the present invention, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.
[0254] All raw materials involved in the synthesis embodiments of the present invention can be purchased from the market or obtained by conventional preparation methods in the art;
[0255] Preparation of compounds
[0256] 1. Synthesis of intermediate P
[0257] Synthesis of intermediate P1:
[0258]
[0259] Add raw material R2 (25 mmol, 7.3 g), potassium carbonate (62.5 mmol, 8.6 g), tricyclohexylphosphine (1.25 mmol, 0.35 g), and palladium acetate (0.4 mmol, 90 mg) to a two-necked flask. Add 160 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 45 minutes. Add raw material R1 (25 mmol, 6.7 g) under nitrogen protection and stir at 140 °C for 12 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate P1.
[0260] Synthesis of intermediate P2:
[0261]
[0262] Add raw material R3 (18.4 mmol, 3.9 g) and cesium carbonate (55.2 mmol, 18.0 g) to a two-necked flask. Add 120 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add intermediate P1 (20.2 mmol, 8.7 g) under nitrogen protection. Reflux the solution under magnetic stirring for 20 hours. Cool, filter, wash with water, dry, and pass through a column to obtain intermediate P2.
[0263] Synthesis of intermediate P3:
[0264]
[0265] In a three-necked flask under nitrogen protection, 2.5 g (10 mmol) of starting material R4, 3.4 g (10 mmol) of starting material R5, 5.6 g (25 mmol) of zinc bromide, and 180 mL of anhydrous toluene were added, and the mixture was heated to 110 °C and reacted for 14 hours. After cooling to room temperature, the mixture was concentrated and purified by silica gel column chromatography to obtain intermediate X1.
[0266] Intermediate X1 (1.2 g, 2.5 mmol) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at 0 °C, 1.6 mL of n-butyllithium (1.6 M) n-hexane solution was slowly added. After stirring at 0 °C for 2 hours, 5 mL of tetrahydrofuran solution of starting material M1 (0.5 g, 2.8 mmol) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water, and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and slowly quenched with an aqueous solution of NaHCO3. The aqueous layer was then separated and extracted with dichloromethane. The product was dried over sodium sulfate, filtered, and evaporated by rotary evaporation. The solution was then column-purified to give intermediate P3.
[0267] Synthesis of intermediate P4:
[0268]
[0269] The preparation method of intermediate P4 is the same as that of intermediate P1, except that raw material R6 is used to replace raw material R2 to obtain intermediate P4.
[0270] Synthesis of intermediate P5:
[0271]
[0272] The preparation method of intermediate P5 is the same as that of intermediate P2, except that intermediate P4 is used to replace intermediate P2 to obtain intermediate P5.
[0273] Synthesis of intermediate P6:
[0274]
[0275] The preparation method of intermediate P6 is the same as that of intermediate P2, except that raw material R7 is used to replace intermediate P2 to obtain intermediate P6.
[0276] Synthesis of intermediate P7:
[0277]
[0278] The preparation method of intermediate P7 is the same as that of intermediate P2, except that intermediate P3 is used to replace intermediate P2 to obtain intermediate P7.
[0279] Synthesis of intermediate P8:
[0280]
[0281] Add raw material R2 (25 mmol, 7.3 g), potassium carbonate (62.5 mmol, 8.6 g), tricyclohexylphosphine (1.25 mmol, 0.35 g), and palladium acetate (0.4 mmol, 90 mg) to a two-necked flask. Add 160 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 45 minutes. Add raw material R8 (25 mmol, 6.7 g) under nitrogen protection and stir at 140 °C for 15 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate P8.
[0282] Synthesis of intermediate P9:
[0283]
[0284] The preparation method of intermediate P9 is the same as that of intermediate P2, except that intermediate P8 is used to replace intermediate P2 to obtain intermediate P9.
[0285] 2. Synthesis of intermediate Q
[0286] Synthesis of intermediate Q1:
[0287]
[0288] Add raw material D1 (18.4 mmol, 6.2 g) and cesium carbonate (55.2 mmol, 18.0 g) to a two-necked flask. Add 120 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add raw material A4 (20.2 mmol, 5.6 g) under nitrogen protection. Reflux the solution under magnetic stirring for 24 hours. Cool, filter, wash with water, dry, and pass through a column to obtain intermediate Y1.
[0289]
[0290] Intermediate Y1 (5.1 mmol, 3.0 g) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.7 mL of n-butyllithium (2.5 M, 11.7 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 2 hours, 15 mL of tetrahydrofuran solution of starting material M1 (5.5 mmol, 1.0 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 20 mL of dilute hydrochloric acid (1.0 M), distilled water, and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and then slowly quenched with an aqueous sodium bicarbonate (NaHCO3) solution. Next, the aqueous layer was separated, extracted with dichloromethane, dried with sodium sulfate, filtered, distilled under reduced pressure, and passed through a column to obtain intermediate Q1.
[0291] Synthesis of intermediate Q2:
[0292]
[0293] The preparation method of intermediate Q2 is the same as that of intermediate Q1, except that raw material M2 is used to replace raw material M1 to obtain intermediate Q2.
[0294] Synthesis of intermediate Q3:
[0295]
[0296] The preparation method of intermediate Q3 is the same as that of intermediate Q1, except that raw material M3 is used to replace raw material M1 to obtain intermediate Q3.
[0297] Synthesis of intermediate Q4:
[0298]
[0299] Under nitrogen protection, starting material R3 (0.52 g, 2.5 mmol) was dissolved in 50 mL of toluene solution, and 4-tert-butylaniline (0.37 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol), and palladium acetate (0.01 g, 0.05 mmol) were added, followed by vigorous stirring. The resulting mixture was heated under reflux for 4 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed with deionized water (100 mL), dried over anhydrous magnesium sulfate, cooled to room temperature, filtered, concentrated, and subjected to column chromatography to obtain intermediate Y2.
[0300] Under nitrogen protection, intermediate Y2 (2.78 g, 10 mmol) and p-toluenesulfonic acid (0.17 g, 1 mmol) were added to a two-necked flask, heated to 150 °C and stirred for 0.5 hours. Then, starting material M2 (3.51 g, 12 mmol) was added, and the reaction was heated to 200 °C and reacted for 1 hour. After cooling to room temperature, the mixture was concentrated and subjected to column chromatography to obtain intermediate Q4.
[0301] Synthesis of intermediate Q5:
[0302]
[0303] Raw material Q1 (1.58 g, 2.5 mmol) was dissolved in 50 mL of toluene solution. Raw material A1 (0.37 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol), and palladium acetate (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 5 hours, and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed three times with deionized water (100 mL). After drying overnight with anhydrous magnesium sulfate, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether with stirring, and filtered to give intermediate Y3.
[0304] Under nitrogen protection, intermediate Y3 (6.99 g, 10 mmol) and p-toluenesulfonic acid (1.7 g, 10 mmol) were added to a two-necked flask, heated to 150 °C and stirred for 5 hours. Then, starting material M1 (2.16 g, 12 mmol) was added, and the reaction was heated to 200 °C and reacted for 1 hour. After cooling to room temperature, the mixture was concentrated and subjected to column chromatography to obtain intermediate Q5.
[0305] Synthesis of intermediate Q6:
[0306]
[0307] Raw material D2 (0.68 g, 2.5 mmol) was dissolved in 50 mL of toluene solution. Raw material A1 (0.75 g, 5.0 mmol), tri-tert-butylphosphine (0.050 g, 0.25 mmol), sodium tert-butoxide (1.25 g, 13 mmol), and palladium acetate (0.018 g, 0.08 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 10 hours, and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed three times with deionized water (100 mL). After drying overnight with anhydrous magnesium sulfate, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether with stirring, and filtered to give intermediate Y4.
[0308]
[0309] Under nitrogen protection, intermediate Y4 (4.07 g, 10 mmol) and p-toluenesulfonic acid (3.44 g, 20 mmol) were added to a two-necked flask, and the mixture was heated to 150 °C and stirred for 6 hours. Then, starting material M1 (4.33 g, 24 mmol) was added, and the reaction was heated to 200 °C and reacted for 3 hours. After cooling to room temperature, the mixture was concentrated and subjected to column chromatography to obtain intermediate Y5.
[0310] Intermediate Y5 (1.83 g, 2.5 mmol) was dissolved in 50 mL of toluene solution. Starting material D3 (0.53 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol), and palladium acetate (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 4 hours, then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed three times with deionized water (100 mL). After drying overnight with anhydrous magnesium sulfate, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether with stirring, and filtered to obtain intermediate Q6.
[0311] Synthesis of intermediate Q7:
[0312]
[0313] Raw material Q2 (1.86 g, 2.5 mmol) was dissolved in 50 mL of toluene solution. Raw material A1 (0.37 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol), and palladium acetate (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 4 hours, and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed three times with deionized water (100 mL). After drying overnight with anhydrous magnesium sulfate, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether with stirring, and filtered to give intermediate Y6.
[0314] Under nitrogen protection, intermediate Y6 (8.12 g, 10 mmol) and p-toluenesulfonic acid (1.7 g, 10 mmol) were added to a two-necked flask, and the mixture was heated to 150 °C and stirred for 5 hours. Then, starting material M1 (2.16 g, 12 mmol) was added, and the reaction was heated to 200 °C and reacted for 1 hour. After cooling to room temperature, the mixture was concentrated and subjected to column chromatography to obtain intermediate Q7.
[0315] Synthesis of intermediate Q8:
[0316]
[0317] Under nitrogen protection, intermediate Y6 (8.12 g, 10 mmol) and p-toluenesulfonic acid (1.7 g, 10 mmol) were added to a two-necked flask, and the mixture was heated to 150 °C and stirred for 5 hours. Then, starting material M2 (3.51 g, 12 mmol) was added, and the reaction was heated to 200 °C and reacted for 1 hour. After cooling to room temperature, the mixture was concentrated and subjected to column chromatography to obtain intermediate Q8.
[0318] 3. Synthesis of the Examples
[0319] Example 1: Synthesis of compound FGD-2:
[0320]
[0321] Intermediate Q1 (11 mmol, 6.94 g), starting material A1 (5 mmol, 0.75 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (30 mmol, 2.88 g), and toluene (160 mL) were added sequentially to a three-necked flask. The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 25 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate J1.
[0322]
[0323] In a three-necked flask under nitrogen protection, intermediate J1 (2 mmol, 2.50 g) and 60 mL of tert-butylbenzene were added. A 1.6 M tert-butyllithium solution in pentane (5 mmol, 3.1 mL) was slowly added at -40 °C, and the mixture was heated to 60 °C and reacted for 6 hours. Then, boron tribromide (5 mmol, 0.5 mL) was added at -40 °C, and the mixture was slowly brought to room temperature and reacted for another 8 hours. Next, N,N-diisopropylethylamine (5 mmol, 0.9 mL) was added to the mixture at 0 °C, and the mixture was heated to 120 °C and reacted for another 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, quenched with methanol, and the organic layer was concentrated under reduced pressure. The resulting product was purified by silica gel column chromatography and dried under vacuum to obtain compound FGD-2.
[0324] The following target compounds were synthesized following the same procedure as in Example 1 for preparing compound FGD-2; the reaction conditions were the same, except that starting material A and intermediate Q listed in Table 1-1 were used.
[0325] Table 1-1
[0326]
[0327] Example 4: Synthesis of compound FGD-7:
[0328]
[0329] Intermediate Q1 (5.5 mmol, 3.47 g), starting material A3 (5 mmol, 0.47 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (15 mmol, 1.44 g), and toluene (80 mL) were added sequentially to a three-necked flask. The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 24 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate J2.
[0330]
[0331] Intermediate Q2 (5.5 mmol, 4.09 g), intermediate J2 (5 mmol, 3.22 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (15 mmol, 1.44 g), and toluene (160 mL) were added sequentially to a three-necked flask. The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 24 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate K2.
[0332]
[0333] In a three-necked flask under nitrogen protection, intermediate K2 (2 mmol, 2.61 g) and 100 mL of tert-butylbenzene were added. A 1.6 M tert-butyllithium solution in pentane (5 mmol, 3.1 mL) was slowly added at -40 °C, and the mixture was heated to 60 °C and reacted for 9 hours. Then, boron tribromide (5 mmol, 0.5 mL) was added at -40 °C, and the mixture was slowly brought to room temperature and reacted for another 6 hours. Next, N,N-diisopropylethylamine (5 mmol, 0.9 mL) was added to the mixture at 0 °C, and the mixture was heated to 120 °C and reacted for another 10 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, quenched with methanol, and the organic layer was concentrated under reduced pressure. The resulting product was purified by silica gel column chromatography and dried under vacuum to obtain compound FGD-7.
[0334] The following target compounds were synthesized following the same procedure as in Example 4 for the preparation of compound FGD-7; the reaction conditions were the same, except that starting material A and intermediate Q and intermediate Q / starting material B were used as listed in Tables 1-2 below;
[0335] Table 1-2
[0336]
[0337] Example 9: Synthesis of compound FGD-26:
[0338]
[0339] Under nitrogen protection, raw material A4 (6.99 g, 25 mmol), cesium carbonate (20.36 g, 62.5 mmol), intermediate Q4 (13.80 g, 25 mmol) and 300 mL of anhydrous DMF were added to a two-necked flask. The mixture was heated under reflux and stirred for 10 hours under nitrogen protection, cooled to room temperature, filtered, washed with water, dried, and passed through a column to obtain intermediate J9.
[0340]
[0341] Intermediate J9 (2.03 g, 2.5 mmol) was dissolved in 80 mL of toluene solution. Starting material B1 (1.17 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol), and palladium acetate (0.01 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 10 hours, and then allowed to reach room temperature. The mixture was concentrated under reduced pressure and separated by column chromatography to obtain intermediate K9.
[0342] Intermediate K9 (14.99 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 18.75 mL of a 1.6 M tert-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 4 hours, boron tribromide (12.53 g, 50 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 3 hours. N,N-diisopropylethylamine (DIPEA) (6.59 g, 51 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 6 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed under vacuum and column chromatography to give compound FGD-26.
[0343] The following target compounds were synthesized following the same procedure as in Example 9 for the preparation of compound FGD-26; the reaction conditions were the same, except that the starting material A / intermediate P, intermediate Q and starting material A / starter B / intermediate P listed in Tables 1-3 below were used.
[0344] Table 1-3
[0345]
[0346]
[0347] Example 15 Synthesis of compound FGD-35:
[0348]
[0349] Add raw material C1 (0.66 g, 2.5 mmol) and cesium carbonate (2.61 g, 8 mmol) to a two-necked flask. Add 50 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 min. Add intermediate P1 (1.08 g, 2.5 mmol) under nitrogen protection and stir at 140 °C for 5 h under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate Y15.
[0350] Intermediate Y15 (1.69 g, 2.5 mmol) was dissolved in 50 mL of toluene solution. Starting material A1 (0.37 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol), and palladium acetate (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 10 hours, and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed three times with deionized water (100 mL). After drying overnight with anhydrous magnesium sulfate, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether with stirring, and filtered to obtain intermediate J15.
[0351]
[0352] Intermediate J15 (1.86 g, 2.5 mmol) was dissolved in 200 mL of toluene solution. Starting material B1 (1.17 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol), and palladium acetate (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 10 hours, and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed three times with deionized water (100 mL). After drying overnight with anhydrous magnesium sulfate, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether with stirring, and filtered to obtain intermediate K15.
[0353] Intermediate K15 (14.17 g, 12.5 mmol) was dissolved in 350 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 12.5 mL of a 2.5 M tert-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 4 hours, boron tribromide (9.39 g, 37.5 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 3 hours. N,N-diisopropylethylamine (DIPEA) (8.08 g, 62.5 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 14 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed under vacuum and column chromatography to give compound FGD-35.
[0354] The following target intermediates were synthesized following the preparation process of intermediate J15 in Synthesis Example 15; the reaction conditions were the same, except that the starting material C, intermediate P and starting material A listed in Table 1-4-1 were used.
[0355] Table 1-4-1
[0356]
[0357] The following target compounds were synthesized following the preparation process of compound FGD-35 in Synthesis Example 15; the reaction conditions were the same, except that intermediates J and P / starting material B listed in Table 1-4-2 were used.
[0358] Table 1-4-2
[0359]
[0360]
[0361]
[0362] Example 24 Synthesis of compound FGD-53:
[0363]
[0364] Intermediate Q5 (2.15 g, 2.5 mmol) was dissolved in 50 mL of toluene solution. Starting material B1 (1.17 g, 2.5 mmol), 2-dicyclohexylphosphine-2',6'-diisopropoxy-1,1'-biphenyl (0.058 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol), and palladium acetate (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 8 hours, and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed three times with deionized water (100 mL). After drying overnight with anhydrous magnesium sulfate, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether with stirring, and filtered to obtain intermediate K24.
[0365] Intermediate K24 (15.62 g, 12.5 mmol) was dissolved in 350 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 12.5 mL of a 2.5 M tert-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 4 hours, boron tribromide (9.39 g, 37.5 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 3 hours. N,N-diisopropylethylamine (DIPEA) (8.08 g, 62.5 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 10 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed under vacuum and column chromatography to give compound FGD-53.
[0366] The following target compounds were synthesized following the same procedure as compound FGD-53 in Synthesis Example 24; the reaction conditions were the same, except that intermediates Q and P / starting material B listed in Tables 1-5 were used.
[0367] Table 1-5
[0368]
[0369]
[0370] The following describes in detail the application effects of the composition formed by the first host material, the second host material, and the double-boron fluorescent material of the present invention in organic electroluminescent devices through device examples 1-46 and device comparative examples 1-8. Device examples 2-46 and device comparative examples 1-8 of the present invention have the same fabrication process as device example 1, and use the same substrate material and electrode material, with the same electrode film thickness. The only difference is the replacement of the material in the light-emitting layer of the device. The layer structure and test results of each device example are shown in Tables 3 and 4, respectively.
[0371] Device Example 1
[0372] The device structure in this embodiment is as follows: Figure 1 As shown, the preparation method is as follows:
[0373] The transparent substrate layer 1 is a transparent glass substrate. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet light and ozone to remove organic residues from the transparent ITO surface. After the above washing, a 10nm thick layer of HT-1 and HI-1 is deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Subsequently, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the organic electroluminescent device is fabricated, using PH-18 and NH-2 as the host materials and FGD-2 as a boron-containing phosphor, with a mass ratio of PH-18, NH-2, and FGD-2 of 69:30:1. The light-emitting layer has a film thickness of 30nm. Following the aforementioned light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer serves as the hole-blocking layer 7. Following the hole-blocking layer 7, ET-1 and Liq are vacuum-deposited at a mass ratio of 1:1, resulting in a film thickness of 30 nm; this layer serves as the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 9. On the electron injection layer 9, an 80 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 10.
[0374]
[0375]
[0376] Device Examples 2-30
[0377] The only difference from Device Example 1 is that a different double-boron fluorescent material is used in the light-emitting layer, as shown in Table 3. All other conditions are the same.
[0378] Device Examples 31-33
[0379] The only difference from Device Example 1 is that different first and second host materials are used in the light-emitting layer, as shown in Table 3. All other conditions are the same.
[0380] Device Example 34
[0381] The only difference from device example 1 is the addition of a phosphorus photosensitizer, as shown in Table 3.
[0382] Device Examples 35-46
[0383] The only difference from Device Example 1 is that different first host materials, second host materials, and double boron fluorescent materials are used in the light-emitting layer, and a phosphorus photosensitizer is added, as shown in Table 3.
[0384] Device Comparison Examples 1-4
[0385] The only difference from Device Example 1 is that a different double-boron fluorescent material is used in the light-emitting layer, as shown in Table 3. All other conditions are the same.
[0386] Device Comparison Examples 5-8
[0387] The only difference from Device Example 1 is that a different double-boron fluorescent material is used in the light-emitting layer, and a phosphorus photosensitizer is added, as shown in Table 3.
[0388] After completing the organic electroluminescent device as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency and lifetime of the device are measured. Examples and comparative examples of devices prepared using the same method are shown in Table 3; the test results for the current efficiency and lifetime of the obtained devices are shown in Table 4.
[0389] Table 3
[0390]
[0391]
[0392]
[0393]
[0394]
[0395] Table 4
[0396]
[0397]
[0398] The current efficiency was tested using an IVL (current-voltage-brightness) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.
[0399] The material and device performance parameters provided in this invention are not limited by testing methods.
[0400] As can be seen from the device data results in Table 4, in the non-sensitized device system, compared with the devices in Comparative Examples 1-4, the organic electroluminescent devices using the light-emitting layer composition of the present invention have achieved a significant improvement in current efficiency and lifetime.
[0401] In the phosphorescently sensitized device system, compared with the devices in Comparative Examples 5-8, the organic electroluminescent devices using the light-emitting layer composition of the present invention show a significant improvement in current efficiency and lifetime after sensitization with phosphorescent materials.
[0402] In summary, the above are merely preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.
Claims
1. A composition for a light-emitting layer, comprising a first host material, a second host material, and a boron-containing fluorescent material, characterized in that, The first main material is selected from the structure shown in general formula (A-1) or general formula (A-2): In general formulas (A-1) and (A-2), X represents an O atom, a S atom, or a N (-L4-Ar) atom. d ); L1, L2, L3, and L4 are independently represented as single bonds, substituted bonds, or unsubstituted C6-C6 bonds, respectively. 30 arylene, C2-C, substituted or unsubstituted 30 heteroaryl groups; Ar a Ar b Ar c Ar d Each can be independently represented as either substituted or unsubstituted C3-C3. 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Ring A represents a benzene ring that is either substituted or unsubstituted; R m R n R p R q Each occurrence is independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, C1-C10 alkyl group (substituted or unsubstituted), and C3-C6 alkyl group (substituted or unsubstituted). 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C1-C2 groups 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; i, j, s, and k are each independently represented as 0, 1, 2, 3, or 4; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorinated alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; In the structures shown in general formulas (A-1) and (A-2), any hydrogen atom may optionally be partially or completely replaced by deuterium; The second main material is selected from the structure shown in general formula (B): In general formula (B), L5, L6, and L7 are each independently represented as single bonds, substituted by substituents, or unsubstituted C6 to C7 bonds, respectively. 30 arylene, C2-C, substituted or unsubstituted 30 heteroaryl groups; Ar e Ar f Ar g Each occurrence is independently represented as a hydrogen atom, or as a C3-C atom substituted or unsubstituted. 10 Cycloalkyl, C6-C6 substituted or unsubstituted 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorinated alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; In the structure shown in general formula (B), any hydrogen atom may optionally be partially or completely replaced by deuterium; Compounds excluded from general formula (B) The boron-containing fluorescent material is selected from the structure shown in general formula (C-1) or general formula (C-2): In general formulas (C-1) and (C-2), the recurrence of Z being the same or different is represented by C-(R). o ); The R o Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the following: heteroaryl, C2-C30 borane alkyl group substituted or unsubstituted, and C3-C30 silane alkyl group substituted or unsubstituted; Rings M1, M2, M3, and M4 represent C6-C6 rings substituted or unsubstituted with one or more R groups. 30 aryl group, C2-C2 substituted or unsubstituted by one or more R groups. 30 Heteroaryl, C6-C substituted or unsubstituted with one or more R groups 30 The aliphatic ring, C formed by the fusion of two or more aromatic rings, heteroaromatic rings, or aliphatic rings, substituted or unsubstituted with one or more Rs. 10 ~C 30 One type of fused ring; Each occurrence of R, whether the same or different, represents a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the following: heteroaryl, C2-C30 borane alkyl group substituted or unsubstituted, and C3-C30 silane alkyl group substituted or unsubstituted; The replacement of R is either a single bond or a parallel ring connection; Ar1, Ar2, Ar3, Ar4, and Ar5 are independently represented as C1 to C5 groups, substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; X'1, X'2, X'3, and X'4 are independently represented as single bonds, -O-, -S-, and -N(R) bonds, respectively. d )-、-B(R e )-、-C(R f (R) g )-、-Si(R h (R) i - or -C(Rj)=C(R) k )-; p, q, i, j represent 0 or 1; And at least one of X'2, X'3, and X'4 exists and is represented as -B(R). e )-; The R d R e R f R g R h R i R j R k Individually represented as C1 to C2 cells substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The R f With R g Between, R h With R i Between, R d With adjacent R o Between, R e With adjacent R o Between, R d Between M1 and R e Between M1 and R d Between M2 and R e Between M2 and Ar1 and adjacent R o Between, between Ar1 and M3, between Ar2 and Ar3, and any adjacent R o The components, Ar5 and M4, are either not connected or connected in a loop; The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.
2. The composition for the light-emitting layer according to claim 1, characterized in that, The first main material is selected from the structure shown in any one of general formulas (A-3) to (A-8): In general formulas (A-3) to (A-8), L1, L2, L3, and L4 are each independently represented as a single bond, substituted with a substituent, or unsubstituted C6 to C6 bonds, respectively. 30 arylene, C2-C, substituted or unsubstituted 30 heteroaryl groups; The Ar a Ar b Ar c Ar d Each occurrence is independently represented as either substituted or unsubstituted C3-C3. 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The R m R n R p R q Each occurrence is independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C1-C2 groups 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The i, j, s, and k are each independently represented as 0, 1, 2, 3, or 4; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorinated alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; In the structures shown in general formulas (A-3) to (A-8), any hydrogen atom may optionally be partially or completely replaced by deuterium; Preferably, the first main material is selected from the structure shown in any one of general formulas (A-9) to (A-22): In general formulas (A-9) to (A-22), L1, L2, L3, and L4 are each independently represented as single bonds, substituted with substituents, or unsubstituted C6 to C6 bonds, respectively. 30 arylene, C2-C, substituted or unsubstituted 30 heteroaryl groups; The Ar a Ar b Ar c Ar d Each occurrence is independently represented as either substituted or unsubstituted C3-C3. 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The R m R n R p R q Each occurrence is independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C1-C2 groups 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The i, j, s, and k are each independently represented as 0, 1, 2, 3, or 4; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorinated alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; In the structures shown in general formulas (A-9) to (A-22), any hydrogen atom may optionally be partially or completely replaced by deuterium.
3. The composition for the light-emitting layer according to claim 1, characterized in that, The first main material is selected from the structure shown below:
4. The composition for the light-emitting layer according to claim 1, characterized in that, The second main material is selected from the structure shown in any one of general formulas (B-1) to (B-4): In general formulas (B-1) to (B-4), X' represents an O atom, a S atom, or a N (-L8-Ar atom). h ) or C(Rv)(Rz); "X" represents an O atom, an S atom, an N-ph, a dimethyl-substituted methylene or a diphenyl-substituted methylene; L5, L6, L7, and L8 are independently represented as single bonds, C6 to C8 bonds substituted with substituents, or C6 to C8 bonds that are unsubstituted, respectively. 30 arylene, C2-C, substituted or unsubstituted 30 heteroaryl groups; The Ar f Ar g Ar h Each of the C3 to C3 atoms can be represented independently as a hydrogen atom, substituted or unsubstituted. 10 Cycloalkyl, C6-C6 substituted or unsubstituted 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Ring B represents a benzene ring that is either substituted or unsubstituted; Ra, R b Each can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C1-C2 groups 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; g and h can be independently represented as 0, 1, 2, 3 or 4 respectively; Each occurrence of Rv and Rz independently represents either a C1-C1 column substituted with or unsubstituted with a substituent. 10 Alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Rv and Rz are not connected or are connected via a single key; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorinated alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; In the structures shown in general formulas (B-1) to (B-4), any hydrogen atom may optionally be partially or completely replaced by deuterium; Compounds excluded from general formula (B-4) Preferably, the second main material is selected from the structure shown in any one of general formulas (B-5) to (B-10): In general formulas (B-5) to (B-10), X' represents an O atom, a S atom, or a N (-L8-Ar atom). h ) or C(Rv)(Rz); L5, L6, L7, and L8 are independently represented as single bonds, C6 to C8 bonds substituted with substituents, or C6 to C8 bonds that are unsubstituted, respectively. 30 arylene, C2-C, substituted or unsubstituted 30 heteroaryl groups; The Ar f Ar g Ar h Each of the C3 to C3 atoms can be represented independently as a hydrogen atom, substituted or unsubstituted. 10 Cycloalkyl, C6-C6 substituted or unsubstituted 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; R a R b Each can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C1-C2 groups 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; g and h can be independently represented as 0, 1, 2, 3 or 4 respectively; Each occurrence of Rv and Rz independently represents either a C1-C1 column substituted with or unsubstituted with a substituent. 10 Alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Rv and Rz are not connected or are connected via a single key; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorinated alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; In the structures shown in general formulas (B-5) to (B-10), any hydrogen atom may optionally be partially or completely replaced by deuterium; Preferably, the second body material is selected from the structure shown in any one of general formulas (B-11) to (B-16): In general formulas (B-11) to (B-16), L5, L6, L7, and L8 are independently represented as single bonds, C6 to C8 bonds substituted with substituents, or C6 to C8 bonds that are unsubstituted. 30 arylene, C2-C, substituted or unsubstituted 30 heteroaryl groups; The Ar f Ar g Ar h Each of the C3 to C3 atoms can be represented independently as a hydrogen atom, substituted or unsubstituted. 10 Cycloalkyl, C6-C6 substituted or unsubstituted 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; R a R b Each can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C3-C6 substituted or unsubstituted 10 Heterocyclic alkyl groups, substituted or unsubstituted C1-C2 groups 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; g and h can be independently represented as 0, 1, 2, 3 or 4 respectively; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorinated alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; In the structures shown in formulas (B-11) to (B-16), any hydrogen atom may optionally be partially or completely replaced by deuterium.
5. The composition for the light-emitting layer according to claim 1, characterized in that, The second main material is selected from the structure shown below:
6. The composition for the light-emitting layer according to claim 1, characterized in that, The boron-containing fluorescent material is selected from any one of general formulas (C-3) to (C-7): In general formulas (C-3) to (C-7), the meanings of Z, Ar1, Ar2, Ar3, Ar4, Ar5, and M1 are the same as those defined in claim 1; Z1, Z2, Z3, Z4, Z5, Z6, and Z7 are independently represented as C-(R1), C-(R2), C-(R3), C-(R4), C-(R5), C-(R6), and C-(R7); R1, R2, R3, R4, R5, R6, and R7 are independently represented as a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, and C1-C1 atoms substituted or unsubstituted with substituents, respectively. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the following: heteroaryl, C2-C30 borane alkyl group substituted or unsubstituted, and C3-C30 silane alkyl group substituted or unsubstituted; Ar1 and R3 are either not connected or connected in a loop; Ar1 and R4 are either not connected or connected in a loop; Ar1 and R5 are either not connected or connected in a loop; The Ar2 and Ar3 rings are either not connected or connected to form a ring; R6 and R7 are either not connected or connected in a loop; The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B; Preferably, the boron-containing fluorescent material is selected from the structure shown in any one of general formulas (D-1) to (D-23): In general formulas (D-1) to (D-23), Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and Ar7 are independently represented as C1 to C7 groups, substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 Each of the following can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the following: heteroaryl, C2-C30 borane alkyl group substituted or unsubstituted, and C3-C30 silane alkyl group substituted or unsubstituted; m1, m2, m3, m4, m5, m6, m7, m8, m9, m 10 m 11 m 12 Represented as 0 to the maximum allowed number of substitutions; X'4 represents a single bond, -O-, -S-, -N(R) d )-、-B(R e )-、-C(R f (R) g )-、-Si(R h (R) i - or -C(Rj)=C(R) k )-; q represents 0 or 1; The R d R e R f R g R h R i R j R k Individually represented as C1 to C2 cells substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The R f With R g Between, R h With R i They are either not connected or connected in a loop; The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B; Preferably, the boron-containing fluorescent material is selected from any one of general formulas (E-1) to (E-23): General Formula (E-3) General Formula (E-4) In general formulas (E-1) to (E-23), Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and Ar7 are independently represented as C1 to C7 groups, substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 Each of the following can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the following: heteroaryl, C2-C30 borane alkyl group substituted or unsubstituted, and C3-C30 silane alkyl group substituted or unsubstituted; X'4 represents a single bond, -O-, -S-, -N(R) d )-、-B(R e )-、-C(R f (R) g )-、-Si(R h (R) i - or -C(Rj)=C(R) k )-; q represents 0 or 1; The R d R e R f R g R h R i R j R k Individually represented as C1 to C2 cells substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The R f With R g Between, R h With R i They are either not connected or connected in a loop; The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.
7. The composition for the light-emitting layer according to claim 1, characterized in that, The boron-containing fluorescent material is selected from the following specific structures: Any one of them.
8. The composition for the light-emitting layer according to any one of claims 1-7, characterized in that, It also includes a sensitizing material, which is a phosphorescent sensitizing material or a TADF sensitizing material; preferably, the phosphorescent sensitizing material is a metal complex containing iridium or platinum.
9. An organic electroluminescent device, comprising, in sequence, a substrate, a first electrode, an organic functional layer, and a second electrode, wherein the organic functional layer is located between the first electrode and the second electrode, characterized in that, The organic functional layer comprises the composition for the light-emitting layer according to any one of claims 1-8.
10. The organic electroluminescent device according to claim 9, wherein the organic functional layer comprises at least one light-emitting layer, characterized in that, The light-emitting layer comprises the composition for the light-emitting layer according to any one of claims 1-8; Preferably, the organic functional layer includes a hole transport region, a light-emitting layer, and an electron transport region, wherein the light-emitting layer comprises the light-emitting layer composition according to any one of claims 1-8.
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