CN115819440A - Fluorescent emission material and organic electroluminescent device - Google Patents
Fluorescent emission material and organic electroluminescent device Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 50
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- LJHHJFAUMZLYRE-UHFFFAOYSA-N 2-(2,3-dimethylindolo[3,2-b]quinoxalin-6-yl)ethyl-dimethylazanium;chloride Chemical compound Cl.CC1=C(C)C=C2N=C3N(CCN(C)C)C4=CC=CC=C4C3=NC2=C1 LJHHJFAUMZLYRE-UHFFFAOYSA-N 0.000 claims abstract description 23
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims abstract description 20
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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- -1 aromatic cycloalkane Chemical class 0.000 claims description 2
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- 239000007787 solid Substances 0.000 description 13
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 229910052757 nitrogen Inorganic materials 0.000 description 6
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
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- 238000004020 luminiscence type Methods 0.000 description 5
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- 238000001819 mass spectrum Methods 0.000 description 4
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- HNWFFTUWRIGBNM-UHFFFAOYSA-N 2-methyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C)=CC=C21 HNWFFTUWRIGBNM-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
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- 238000009825 accumulation Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
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- 150000001924 cycloalkanes Chemical group 0.000 description 1
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- 239000007850 fluorescent dye Substances 0.000 description 1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
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Abstract
The invention discloses a fluorescence emission material and an organic electroluminescent device, which are of a fluorescence core-bridging unit-fluorescence core structure, wherein the fluorescence core is furan [2,3-b ] quinoxaline, dibenzo [ f, h ] furan [2,3-b ] quinoxaline, furan [2',3':5,6 pyrazine [2,3-f ] [1, 10] phenanthroline, the bridging units are aromatic rings with different steric hindrance and conjugation sizes. The material has simple synthesis process, is suitable for large-scale industrial production, and can be used as one of the best choices of organic light-emitting layer materials of organic electroluminescent devices.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a fluorescent emission material and an organic electroluminescent device.
Background
Organic light-emitting diodes (OLEDs) are a new information display technology and lighting technology that have the most promising prospects after liquid crystal displays. The research on materials plays a core fundamental role in promoting the research process of OLEDs, and after more than twenty years of development, OLEDs luminescent materials undergo a third-generation development process. The third generation of luminescent materials, thermal Activated Delayed Fluorescence (TADF), can utilize triplet excitons to emit light, and has luminescent properties equivalent to those of phosphorescent materials, but does not contain heavy metals, thus having lower manufacturing cost and diversified molecular structure design strategies. However, the lifetime of the triplet state of the delayed fluorescent material device is too long, which causes the efficiency roll-off of the device to be serious under high brightness, thereby causing poor stability of the device. Subsequently, a delayed fluorescence-sensitized fluorescence mechanism was proposed to overcome the shortcomings of the single delayed fluorescence device. The delayed fluorescence-sensitized fluorescence contains a delayed fluorescence sensitizer and a common fluorescent material in the light emitting layer, and in this mechanism, triplet excitons of the delayed fluorescence tend to transfer energy to the common fluorescent material by means of Dexter to cause exciton loss.
To solve this problem, fluorescent dye molecules tend to introduce bulky steric groups, but this strategy does not solve the triplet exciton loss problem of this system well.
Disclosure of Invention
The invention provides a fluorescent emission material and an organic electroluminescent device aiming at the defects in the prior art, and aims to solve the technical problem of triplet exciton energy loss of a delayed fluorescence sensitization fluorescent system.
The invention adopts the following technical scheme:
a fluorescence emission material is a fluorescence core-bridging unit-fluorescence core structure, wherein the fluorescence core is furan [2,3-b ] quinoxaline, dibenzo [ f, h ] furan [2,3-b ] quinoxaline, furan [2',3':5,6] pyrazine [2,3-f ] [1, 10] phenanthroline, the bridging units are aromatic rings with different steric hindrance and conjugation sizes.
Specifically, the structural general formula of the fluorescent emission material is as follows:
wherein A is a monocyclic, bicyclic and polycyclic alkane skeleton having 1 to 6 ring system condensed or a monocyclic, bicyclic and polycyclic aromatic skeleton having 1 to 6 ring system condensed; x and Y are fluorescent nuclear framework furan [2,3-b ] quinoxaline, dibenzo [ f, h ] furan [2,3-b ] quinoxaline, furan [2',3':5,6 pyrazine [2,3-f ] [1, 10] phenanthroline.
Further, the structure of a is as follows:
further, the structures of X and Y are as follows:
wherein R is 1 -R 22 Hydrogen atom, chlorine atom, fluorine atom, cyano group, C1-C20 straight chain and branched chain alkyl, C1-C4 is one of phenyl, naphthyl, pyridine, furan, thiophene and pyrrole.
Further, the C1-C20 linear and branched alkyl group is methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, pentyl, hexyl, octyl, heptyl or dodecyl.
Further, the fluorescent emission material is any one of the following compounds:
specifically, the fluorescent core-bridging unit-fluorescent core structure is a three-dimensional structure.
Specifically, the fluorescent emission material can emit blue light, green light, or orange light.
Further, when the bridging unit is monocyclic or non-aromatic cycloalkane, the conjugated system and steric hindrance are small, and blue light is emitted; when the bridging unit is a binary or ternary aromatic condensed ring, the conjugated system and the steric hindrance are moderate, and green light is emitted; when the bridging unit is more than a three-element aromatic condensed ring, a conjugated system and steric hindrance are large, and orange light is emitted.
The invention also provides another technical scheme that the organic electroluminescent device sequentially comprises an ITO anode, a hole injection layer, a hole transport layer, an electron blocking layer, a luminescent layer, a hole blocking layer, an electron transport layer and a cathode from bottom to top, wherein the luminescent layer comprises the fluorescent emission material.
Compared with the prior art, the invention has at least the following beneficial effects:
the invention relates to a fluorescent emission material, which selects furan [2,3-b ] quinoxaline, dibenzo [ f, h ] furan [2,3-b ] quinoxaline, furan [2',3':5,6] pyrazine [2,3-f ] [1, 10] phenanthrene with blue light emission and high luminous efficiency as a luminous unit, has different steric hindrance and conjugate sizes or saturated cycloparaffin as a middle bridging unit, constructs a structure of 'luminous unit-bridging unit-luminous unit', the charge coupling among the luminous units can be conveniently adjusted by the conjugation and steric hindrance of the bridging unit, and the luminous color can also be adjusted by adjusting the charge transfer degree between the luminous unit and the bridging unit; thus, the luminescent color of the material can be adjusted from blue light to green light or even orange light.
Furthermore, the selected luminescence unit furan [2,3-b ] quinoxaline, dibenzo [ f, h ] furan [2,3-b ] quinoxaline, furan [2',3':5,6] pyrazine [2,3-f ] [1, 10] phenanthrene has a luminescence peak positioned in the range of 422nm to 450nm for emitting blue light from deep blue light to blue light, the half-height width of the emission peak can be as narrow as 35nm, and the luminescence efficiency of the blue light of the luminescence unit can reach 58% -78%.
Furthermore, the twist angle between the light-emitting unit and the bridging unit can be adjusted through the conjugation length and steric hindrance of the middle bridging unit, so that the electronic conjugation between the light-emitting unit and the charge transfer between the light-emitting unit and the bridging unit are adjusted and controlled, and the purpose of adjusting and controlling the excited state characteristics is achieved.
Further, the straight-chain and branched alkyl groups of C1-C20 are methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, pentyl, hexyl, octyl, heptyl or dodecyl, so that the solubility of the luminescent molecules in an organic solvent and the mutual distance between the luminescent molecules during solid state accumulation can be regulated, and the quenching of luminescence can be inhibited.
Furthermore, the structural molecule of the 'fluorescent core-bridging unit-fluorescent core' has a twisted structure and a three-dimensional structure, and has a larger distance with a delayed fluorescence sensitizer when being doped into a luminescent layer of delayed fluorescence sensitization, so that the triplet excitons of the delayed fluorescence sensitizer can be inhibited to a certain extent from being directly transferred to the fluorescent molecules in a Dexter mode, and the loss of the triplet excitons in the device is reduced.
Furthermore, a fluorescent material system is established, the material can emit blue light, green light and orange light, is suitable for a delayed fluorescence sensitization fluorescence mechanism, can effectively inhibit efficiency roll-off under high brightness, and has high glass transition temperature and thermal stability.
In conclusion, the material of the invention has simple synthesis process, is suitable for large-scale industrial production, and can be used as one of the best choices of organic light-emitting layer materials of organic electroluminescent devices.
The technical solution of the present invention is further described in detail by the accompanying drawings and embodiments.
Drawings
FIG. 1 is a mass spectrum of example 1;
FIG. 2 is a mass spectrum of example 2;
FIG. 3 is a spectrum of example 3, wherein (a) is a nuclear magnetic spectrum and (b) is a mass spectrum;
FIG. 4 is a spectrum of example 4, wherein (a) is a nuclear magnetic spectrum and (b) is a mass spectrum;
FIG. 5 is a graph of photoluminescence spectra of examples 1, 2,3 and 4;
fig. 6 is a schematic structural view of an organic electroluminescent device according to the present invention.
Detailed Description
The technical solutions of the present invention will be described clearly and completely below, and it should be apparent that the described embodiments are some, but not all, embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
In the present invention, all the embodiments and preferred methods mentioned herein can be combined with each other to form a new technical solution, if not specifically stated.
In the present invention, all the technical features mentioned herein and preferred features may be combined with each other to form a new technical solution, if not specifically stated.
In the present invention, the components referred to or the preferred components thereof may be combined with each other to form a novel embodiment, if not specifically stated.
A "range" disclosed herein can be in the form of one or more lower limits and one or more upper limits, respectively, in terms of lower limits and upper limits.
As used herein, the term "and/or" refers to any and all possible combinations of one or more of the associated listed items and includes such combinations.
In the present invention, unless otherwise specified, the individual reactions or operation steps may be performed sequentially or may be performed in sequence. Preferably, the reaction processes herein are carried out sequentially.
Unless otherwise defined, technical and scientific terms used herein have the same meaning as is familiar to those skilled in the art. In addition, any methods or materials similar or equivalent to those described herein can also be used in the present invention.
The invention provides a fluorescent emission material, which is prepared by selecting a blue fluorescent emission unit with high luminous efficiency: furan [2,3-b ] quinoxaline, dibenzo [ f, h ] furan [2,3-b ] quinoxaline, furan [2',3':5,6] pyrazine [2,3-f ] [1, 10] phenanthroline, a structure of a 'light-emitting unit-bridging unit-light-emitting unit' type is constructed, the structure has high light-emitting efficiency and adjustable light-emitting color, the twist adjustment of a molecular structure is carried out through the steric hindrance of a bridging unit, the adjustment and control of the charge transfer degree between the light-emitting unit and the bridging unit are realized, and the purposes of adjusting and controlling the light-emitting color and the three-dimensional structure are further achieved; the three-dimensional molecular structure is doped with a delayed fluorescence-sensitized light-emitting layer, so that the distance between delayed fluorescence molecules and common fluorescence molecules is increased, and the problem of energy loss of triplet excitons of a delayed fluorescence-sensitized fluorescence system is solved.
The invention relates to a fluorescent emission material, which has a structural general formula (I) as follows:
wherein A is a monocyclic, bicyclic and polycyclic alkane skeleton having 1 to 6 ring system fusions or a monocyclic, bicyclic and polycyclic aromatic skeleton having 1 to 6 ring system fusions, preferably A is of the formula:
x and Y are fluorescent nuclear framework furan [2,3-b ] quinoxaline, dibenzo [ f, h ] furan [2,3-b ] quinoxaline, furan [2',3':5,6 pyrazine [2,3-f ] [1, 10] phenanthroline, wherein X and Y can be the same or different, and X and Y are connected with A at any positions; the specific structure is as follows:
wherein R is 1 -R 22 Is one of hydrogen atom, chlorine atom, fluorine atom, cyano group, C1-C20 straight chain, branched chain alkyl, C1-C4 substituted or unsubstituted aromatic ring, such as phenyl, naphthyl, pyridine, furan, thiophene and pyrrole.
Preferably, the fluorescent emitting material is any one of the following compounds:
referring to fig. 6, an organic electroluminescent device according to the present invention includes an ITO anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and a cathode, wherein the light emitting layer includes a fluorescent emission material.
In the structure of the organic electroluminescent device, HTA-CN is a hole injection layer, TPAC is a hole transport layer, TCTA is an electron blocking layer, MADN is a main body, TPBI is an electron transport layer, and ITO and metal aluminum are respectively used as an anode and a cathode; the fluorescent emitting materials were the embodied compounds (1), (2), (3) and (4).
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are some, but not all embodiments of the present invention. The components of the embodiments of the present invention generally described and illustrated in the figures herein may be arranged and designed in a wide variety of different configurations. Thus, the following detailed description of the embodiments of the present invention, as presented in the figures, is not intended to limit the scope of the invention, as claimed, but is merely representative of selected embodiments of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Synthesis of example (1):
in a dry three-necked bottle, the displaced air was nitrogen, (0.5 g, 68%): 3-bromo-2-phenylfuran [2,3-b]Quinoxaline (0.91g, 2.8mmol), 1,4-bis (4,4,5,5-tetramethyl-1,3,2-dioxoboryl) benzene (0.424g, 1.3mmol), cs 2 CO 3 (2.77g，7.65mmol)and Pd(PPh3) 4 (0.13g, 0.13mmol). Heating to reflux reaction for two days, and after the TCL detection reaction is finished, adding tetrahydrofuran and N, N-dimethylformamide into the reaction system for washing to obtain a solid. The obtained solid is obtained by sublimationPurification gives 0.5g of the product of (1). HRMS (ESI) calcd for C 38 H 22 N 4 O 2 [M+H] + 567.18155, found 567.18022, as shown in FIG. 1.
Synthesis of example (2):
in a dry three-necked flask, the replacement air is nitrogen, 3-bromo-2-phenylfuran [2,3-b]Quinoxaline (0.72g, 2.2 mmol), 4,4' -bis (4,4,5,5-tetramethyl-1,3,2-dioxaboronyl) biphenyl (0.91g, 1.0 mmol), cs 2 CO 3 (2.4g，6.4mmol)，Pd(PPh3) 4 (0.12g, 0.1mmol). Heating to reflux reaction for two days, and after the TCL detection reaction is finished, adding tetrahydrofuran and N, N-dimethylformamide into the reaction system for washing to obtain a solid. The obtained solid was purified by sublimation to obtain 0.45g of (2) as a product. HRMS (ESI) calcd for C 44 H 26 N 4 O 2 [M+H] + 643.21285 and found 643.21203, as shown in FIG. 2.
Synthesis of example (3):
in a dry three-necked flask, the replacement air was nitrogen, 3-bromo-2-phenylfuran [2,3-b]Quinoxaline (0.78g, 2.5 mmol), 9, 10-bis (4,4,5,5-tetramethyl-1,3,2-dioxaboronyl) anthracene (0.5 g,1.16 mmol), cs 2 CO 3 (2.53g，6.9mmol)，Pd(PPh 3 ) 4 (0.14g, 0.13mmol). Heating to reflux reaction for two days, and after the TCL detection reaction is finished, adding tetrahydrofuran and N, N-dimethylformamide into the reaction system for washing to obtain a solid. The obtained solid was purified by sublimation to obtain (3) 0.18 g. 1 H NMR(400MHz,Chloroform-d)δ8.24(d，J＝8.4Hz，2H)，8.13(d，J＝8.3Hz，1H)，8.03(d，J＝8.3Hz，1H)，7.88(ddd，J＝6.7，5.4，3.2Hz，4H)，7.84～7.72(m，2H)，7.74～7.65(m，4H)，7.61～7.54(m，2H)，7.32(ddd，J＝7.7，4.9，3.0Hz，8H)，7.20(t，J＝7.7Hz，2H).HRMS(ESI)calcd for C 46 H 26 N 4 O 2 [M+H] + 667.21285, found667.21314 as shown in FIG. 3.
Synthesis of example (4):
in a dry three-necked flask, the replacement air was nitrogen, 3-bromo-2-phenylfuran [2,3-b]Quinoxaline (0.76g, 2.5 mmol), 4,7-bis (4,4,5,5-tetramethyl-1,3,2-dioxaboronyl) benzene [ c][1，2，5]Thiazole (0.45g, 1.17mmol), cs 2 CO 3 (2.53g，6.9mmol)，Pd(PPh 3 ) 4 (0.13g, 0.12mmol). Heating to reflux reaction for two days, and after TCL detection reaction is finished, adding tetrahydrofuran and N, N' -dimethylformamide into the reaction system for washing to obtain a solid. The solid was further purified by sublimation to give pure (4) 0.22 g. 1 HNMR(600MHz，CDCl3)δ8.30(s，2H)，8.20～8.22(d，J＝12Hz，4H),7.74～7.81(m，8H)，7.43～7.46(t，2H)，7.36～7.38(m,4H)； 13 CNMR(600MHz,CDCl3)δ155.5，149.0，139.4，137.6，134.5，127.2，126.2，124.5，123.7，119.5，107.6；HRMS(ESI)：calcd for C38H20N6O2S[M+H]+625.14412 and found 625.14535, as shown in FIG. 4.
Synthesis of example (18):
in a dry three-necked flask, the displaced air was nitrogen, 6,7-dimethyl-3-bromo-2-phenylfuran [2,3-b]Quinoxaline (0.41g, 1.16mmol), 2,7-bis (4,4,5,5-tetramethyl-1,3,2-dioxaboronyl) -9,9' -spirobifluorene (0.30g, 0.53mmol), cs 2 CO 3 (1.03g，3.2mmol)，Pd(PPh 3 ) 4 (0.061g, 0.053mmol). Heating to reflux reaction for two days, and detecting TCLAfter the reaction is finished, tetrahydrofuran and N, N' -dimethylformamide are added into the reaction system for washing to obtain a solid. The solid was further purified by sublimation to give pure (18) 0.20 g.
Synthesis of example (19):
in a dry three-necked flask, the displaced air was nitrogen, (0.5 g, 68%): 5,6]Pyrazine [2,3-f][1，10]Phenanthroline (1.12g, 2.8mmol), 1,4-bis (4,4,5,5-tetramethyl-1,3,2-dioxoboryl) benzene (0.424g, 1.3mmol), cs 2 CO 3 (2.77g，7.65mmol)and Pd(PPh 3 ) 4 (0.13g, 0.13mmol). Heating to reflux reaction for two days, and after the TCL detection reaction is finished, adding tetrahydrofuran and N, N-dimethylformamide into the reaction system for washing to obtain a solid. The solid obtained is purified by sublimation to give 0.3 g of (19) product. Nuclear magnetic and mass spectrometry are difficult to test due to poor solubility of the resulting product.
The photoelectric properties of the material are as follows:
referring to FIG. 5, compounds (1) and (2) emitted blue light in toluene solution at 470-473 nm. The compounds (3) and (4) emitted highly efficient green light in toluene solution, with emission wavelengths of 515nm and 500nm, respectively.
The luminescent color of the compound is regulated and controlled by the bridging unit, when the conjugation length of the bridging unit is short and the steric hindrance is small, such as a monocyclic aromatic structure or a saturated cycloalkane structure, the material emits blue light, when the conjugation length of the bridging unit is long and the steric hindrance is increased, the material emits red shift, an excited state shows that a charge transfer state between the luminescent unit and the bridging unit emits light and green light or orange light, and when the steric hindrance of the bridging unit is further increased, a twist angle between luminescent cores shows nearly orthogonality, and a three-dimensional spatial conformation is presented.
In summary, the fluorescent emission material and the organic electroluminescent device of the present invention have the advantages of adjustable molecular spatial structure conformation, adjustable luminescent color, three-dimensional structure, and applicability to luminescent dyes of single fluorescent organic electroluminescent devices and fluorescent emission dyes of delayed fluorescence-sensitized fluorescent devices.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (10)
1. A fluorescence emission material is characterized in that the fluorescence emission material is of a fluorescence core-bridging unit-fluorescence core structure, the fluorescence core is furan [2,3-b ] quinoxaline, dibenzo [ f, h ] furan [2,3-b ] quinoxaline, furan [2',3':5,6 pyrazine [2,3-f ] [1, 10] phenanthroline, the bridging units are aromatic rings with different steric hindrance and conjugation sizes.
2. The fluorescent light-emitting material of claim 1, wherein the general structural formula of the fluorescent light-emitting material is as follows:
wherein A is a monocyclic, bicyclic and polycyclic alkane skeleton having 1 to 6 ring system condensed or a monocyclic, bicyclic and polycyclic aromatic skeleton having 1 to 6 ring system condensed; x and Y are fluorescent nuclear framework furan [2,3-b ] quinoxaline, dibenzo [ f, h ] furan [2,3-b ] quinoxaline, furan [2',3':5,6 pyrazine [2,3-f ] [1, 10] phenanthroline.
3. A fluorescent light-emitting material according to claim 2, wherein a has the following structure:
4. a fluorescent light-emitting material according to claim 2, wherein X and Y have the following structures:
wherein R is 1 -R 22 Hydrogen atom, chlorine atom, fluorine atom, cyano group, C1-C20 straight chain and branched chain alkyl, C1-C4 is one of phenyl, naphthyl, pyridine, furan, thiophene and pyrrole.
5. A luminescent material as claimed in claim 3 or 4, wherein the C1-C20 linear, branched alkyl group is methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, pentyl, hexyl, octyl, heptyl or dodecyl.
6. The fluorescent light-emitting material of claim 2, wherein the fluorescent light-emitting material is any one of the following compounds:
7. the fluorescent light-emitting material of claim 1, wherein the fluorescent core-bridging unit-fluorescent core structure is a three-dimensional structure.
8. A fluorescent light-emitting material according to claim 1, wherein the fluorescent light-emitting material is capable of emitting blue, green or orange light.
9. The fluorescent emitting material of claim 8, wherein when the bridging unit is a monocyclic ring or a non-aromatic cycloalkane, the conjugated system and steric hindrance are small, and blue light is emitted; when the bridging unit is a binary or ternary aromatic condensed ring, the conjugated system and the steric hindrance are moderate, and green light is emitted; when the bridging unit is more than a ternary aromatic condensed ring, a conjugated system and steric hindrance are large, and orange light is emitted.
10. An organic electroluminescent device comprising, in order from bottom to top, an ITO 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, and a cathode, wherein the light emitting layer comprises the fluorescent emitting material according to any one of claims 1 to 9.
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| CN111825687A (en) * | 2020-07-20 | 2020-10-27 | 西安交通大学 | Fluorescent emission material and organic electroluminescent device prepared from same |
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| CN111825687A (en) * | 2020-07-20 | 2020-10-27 | 西安交通大学 | Fluorescent emission material and organic electroluminescent device prepared from same |
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