CN114591257A - Spiro compound, electron transport material, and light-emitting device - Google Patents
Spiro compound, electron transport material, and light-emitting device Download PDFInfo
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- CN114591257A CN114591257A CN202210323740.3A CN202210323740A CN114591257A CN 114591257 A CN114591257 A CN 114591257A CN 202210323740 A CN202210323740 A CN 202210323740A CN 114591257 A CN114591257 A CN 114591257A
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- spiro compound
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- 239000000463 material Substances 0.000 title claims abstract description 92
- 150000003413 spiro compounds Chemical class 0.000 title claims abstract description 58
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- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims abstract description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
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- 238000013461 design Methods 0.000 claims description 6
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- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 4
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- GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 3
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- NJESAUCSIMQRGL-UHFFFAOYSA-N 4-bromophenanthrene Chemical compound C1=CC=CC2=C3C(Br)=CC=CC3=CC=C21 NJESAUCSIMQRGL-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
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- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
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- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000001505 phosphinoxide group Chemical group 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Abstract
The embodiment of the application provides a spiro compound, an electron transport material and a light-emitting device, wherein the structural general formula of the spiro compound is shown as the following general formula (I), and in the general formula (I), R1-R8 independently comprise substituted or unsubstituted groups; ar1 and Ar2 at least contain one electron-withdrawing group and cannot be hydrogen at the same time; each of the a ring and the B ring independently includes a substituted or unsubstituted monocyclic or polycyclic aromatic ring, or includes a substituted or unsubstituted phenyl, naphthyl, phenanthrene, fluoranthene, fluorene, thiophene, or furyl group; n is 0 or 1; and in the case that N is 1, X is one of a direct bond, O, S, C and N, wherein when X is a direct bond, the A ring and the B ring can not both be unsubstituted phenyl, the spiro compound has an orthogonal spatial configuration, can reduce intermolecular van der Waals force, is beneficial to preventing crystallization of an electron transport material, and has a rigid structure, and can improve the light emitting efficiency of a light emitting device.
Description
Technical Field
The application relates to the technical field of luminescent materials, in particular to a spiro compound, an electron transport material and a luminescent device.
Background
With the progress of the information industry, organic light-emitting diodes (OLEDs) in light-emitting devices have the advantages of all solid state, self-luminescence, high brightness, high resolution, wide viewing angle, fast response speed, thin thickness, small volume, light weight, capability of using a flexible substrate, low-voltage direct current driving, low power consumption, wide working temperature range and the like, and can be applied to the fields of lighting systems, communication systems, vehicle-mounted display, portable electronic devices, high-definition display, military and the like.
However, in the current light emitting device, the electron transport material is easily crystallized and has insufficient rigidity, and the display performance and the light emitting efficiency of the light emitting device are reduced.
Disclosure of Invention
The application provides a spiro compound, an electron transport material and a luminescent device aiming at the defects of the existing mode, and aims to solve the technical problems that the electron transport material is easy to crystallize and has insufficient rigidity, and the display performance and the luminous efficiency of the luminescent device are reduced in the existing luminescent device.
In a first aspect, the present embodiments provide a spiro compound having a general structural formula as shown in formula (i):
in the general formula (I), R1-R8 each independently include a substituted or unsubstituted design group; ar1 and Ar2 at least contain one electron-withdrawing group and cannot be hydrogen at the same time; each of the a ring and the B ring independently includes a substituted or unsubstituted monocyclic or polycyclic aromatic ring, or includes a substituted or unsubstituted phenyl, naphthyl, phenanthrene, fluoranthene, fluorene, thiophene, or furyl group; n is 0 or 1; in the case where N is 1, X is one of a direct bond, O, S, C, and N, wherein when X is a direct bond, both ring a and ring B cannot be unsubstituted phenyl.
Alternatively, when n in formula (I) is 0, the structural formula is shown as the following formula (II):
alternatively, when X in formula (I) is a direct bond, the general structural formula is shown in the following formula (III):
alternatively, when N is 1 and X is one of O, S, C and N, the structural formula is shown as the following formula (IV):
optionally, the spiro compound comprises at least one of:
the electron-withdrawing group is independently one of pyridyl, pyrimidyl, triazinyl, phosphinyl, nitrile, nitro, oxazolyl, quinoxalinyl, thiazolyl, quinolyl, imidazole, phenylpyrimidine, oxaboronyl, sulfone and derivatives thereof;
the Ar1 and the Ar2 are each independently one of: hydrogen, deuterium, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an alkenyl group, a silyl group, a boron group, an amine group, an arylphosphino group, a phosphinoxide group, an aryl group, a heteroaryl group, or adjacent groups may be bonded to each other to form a ring.
Optionally, the design groups of R1-R8 are each independently one of the following: hydrogen, deuterium, cyano, halogen, nitro, hydroxyl, carbonyl, ester, imide, amide, alkyl, cycloalkyl, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, alkenyl, silyl, boron, amine, phosphine oxide, aryl, heteroaryl, pyridyl, pyrimidinyl, triazinyl, phosphinyl, nitrile, nitro, oxazolyl, quinoxalinyl, thiazolyl, quinolinyl, imidazole, phenylpyrimidine, boroheterocyclyl, sulfone, and derivatives thereof.
Optionally, the a ring and the B ring are each independently one of the following structural formulas:
in a second aspect, embodiments of the present application provide an electron transport material, including the spiro compound described above.
In a third aspect, the present application provides a light emitting device, including a first electrode, a light emitting functional layer, and a second electrode, which are sequentially stacked, where the light emitting functional layer includes an electron transport layer, and the electron transport layer includes the above electron transport material.
Optionally, the light-emitting functional layer further includes a hole blocking layer disposed on a side of the electron transport layer close to the first electrode, and the hole blocking layer includes the above-mentioned electron transport material.
The beneficial technical effects brought by the technical scheme provided by the embodiment of the application comprise:
the application provides a spiro compound, which has an orthogonal spatial configuration, can reduce intermolecular van der Waals force, is beneficial to preventing crystallization of an electron transport material containing the spiro compound, and can further improve the display performance of a light-emitting device containing the electron transport material; the spiro compound has a rigid structure, so that an electron transport material containing the spiro compound has higher glass transition temperature, the stability of the electron transport material is favorably improved, the luminous efficiency of a luminescent device can be further improved, and the service life of the luminescent device can be prolonged; an electron-withdrawing group is introduced into the spiro compound, so that the HOMO and the LUMO can be effectively separated, the adjacent functional layers can be adjusted to be matched, the current carrier transmission is smoother, and the driving voltage of the light-emitting device is further reduced.
Additional aspects and advantages of the present application will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the present application.
Drawings
The foregoing and/or additional aspects and advantages of the present application will become apparent and readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings of which:
fig. 1 is a schematic structural diagram of a cross-sectional film layer of a light emitting device according to an embodiment of the present disclosure.
Description of reference numerals:
1-a first electrode;
2-a light-emitting functional layer; 21-a hole injection layer; 22-a hole transport layer; 23-an electron blocking layer; 24-a light emitting layer; 25-a hole blocking layer; 26-an electron transport layer; 27-electron injection layer.
3-a substrate;
4-a second electrode;
100-light emitting device.
Detailed Description
Embodiments of the present application are described below in conjunction with the drawings in the present application. It should be understood that the embodiments set forth below in connection with the drawings are exemplary descriptions for explaining technical solutions of the embodiments of the present application, and do not limit the technical solutions of the embodiments of the present application.
As used herein, the singular forms "a", "an", "the" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. It will be further understood that the terms "comprises" and/or "comprising," when used in this specification, specify the presence of stated features, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of other features, information, data, steps, operations, elements, components, and/or groups thereof, that may be implemented as required by the art. The term "and/or" as used herein means at least one of the items defined by the term, e.g., "a and/or B" may be implemented as "a", or as "B", or as "a and B".
In the description herein, the terms "one embodiment," "some embodiments," "example," "particular example" or "some examples" or the like are intended to indicate that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the disclosure. The schematic representations of the above terms are not necessarily referring to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be included in any suitable manner in any one or more embodiments or examples.
To make the objects, technical solutions and advantages of the present application more clear, embodiments of the present application will be described in further detail below with reference to the accompanying drawings.
The research and development idea of the application comprises: in general, the hole mobility is higher than the electron mobility in a light emitting device, and in order to realize charge balance transmission and effective recombination of carriers and prevent accumulation of single carriers, an electron transport material plays an important role. At present, the electron transport material is easy to crystallize and has insufficient rigidity, and the display performance and the luminous efficiency of a light-emitting device are reduced.
The following describes the technical solutions of the present application and how to solve the above technical problems with specific embodiments. It should be noted that the following embodiments may be referred to, referred to or combined with each other, and the description of the same terms, similar features, similar implementation steps, etc. in different embodiments is not repeated.
The embodiments of the present application provide a spiro compound having a structural formula shown in general formula (i):
in the general formula (I), R1 to R8 each independently include a substituted or unsubstituted design group; ar1 and Ar2 at least contain one electron-withdrawing group and cannot be hydrogen at the same time; each of the a ring and the B ring independently includes a substituted or unsubstituted monocyclic or polycyclic aromatic ring, or includes a substituted or unsubstituted phenyl, naphthyl, phenanthrene, fluoranthene, fluorene, thiophene, or furyl group; n is 0 or 1; in the case where N is 1, X is one of a direct bond, O, S, C, and N, wherein when X is a direct bond, both ring a and ring B cannot be unsubstituted phenyl.
It is to be noted that the a ring and the B ring each independently include a substituted or unsubstituted monocyclic or polycyclic aromatic ring, and this means that the a ring and the B ring each independently include a substituted monocyclic aromatic ring, an unsubstituted monocyclic aromatic ring, a substituted polycyclic aromatic ring, or an unsubstituted polycyclic aromatic ring; polycyclic means at least two rings.
In the embodiment, the spiro compound has an orthogonal spatial configuration, so that the van der waals force among molecules can be reduced, the crystallization of an electron transport material containing the spiro compound can be prevented, and the display performance of a light-emitting device can be improved; the spiro compound has a high triplet state energy level, and the electron transport material containing the spiro compound has a high triplet state energy level, so that excitons generated in the light emitting layer can be prevented from diffusing to the electron transport layer, and the light emitting efficiency of the light emitting device is improved.
And SP3 hybridization of a central C atom in the spiro compound is utilized to break the conjugation of molecules, so that the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) energy levels are distributed in the upper part and the lower part, and the regulation and control of the energy level of an electron transport material are facilitated, and the reduction of triplet level is prevented; the spiro compound has a rigid structure, so that the electron transport material containing the spiro compound has higher glass transition temperature, the stability of the electron transport material is favorably improved, and the luminous efficiency and the service life of a luminescent device are further improved; meanwhile, the spiro compound adopts an asymmetric spiro structure, so that the symmetry of molecules can be reduced, and the film-forming property of the molecules can be improved.
Optionally, the electron-withdrawing group is independently pyridyl, pyrimidyl, triazinyl, phosphinyl, nitrile, nitro, oxazolyl, quinoxalinyl, thiazolyl, quinolyl, imidazole, phenylpyrimidine, oxaboronyl, sulfone, and derivatives thereof, wherein the derivative refers to one of pyridyl, pyrimidyl, triazinyl, phosphinyl, nitrile, nitro, oxazolyl, quinoxalyl, thiazolyl, quinolyl, imidazole, phenylpyrimidine, oxaboronyl, and sulfone.
In the embodiment, the electron-withdrawing group is introduced into the spiro compound and is connected with the electron group, so that the HOMO and the LUMO can be effectively separated, the energy level of the light-emitting layer can be adjusted to be matched with an adjacent functional layer, and the carrier transmission is smoother.
Alternatively, specific electron-withdrawing groups such as a phosphino group, a cyano group, and an imidazole group are introduced into the spiro compound, so that the injectability of the electron transport material can be improved, and the driving voltage of the light-emitting device can be reduced.
Optionally, Ar1 and Ar2 are each independently one of: hydrogen, deuterium, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an alkenyl group, a silyl group, a boron group, an amine group, an arylphosphino group, a phosphino group, an aryl group, a heteroaryl group, or adjacent groups bonded to each other to form a ring, wherein adjacent groups refer to any two adjacent groups in the structure of the compound.
Alternatively, each of the design groups of R1-R8 is independently one of: hydrogen, deuterium, cyano, halogen, nitro, hydroxyl, carbonyl, ester, imide, amide, alkyl, cycloalkyl, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, alkenyl, silyl, boron, amine, phosphine oxide, aryl, heteroaryl, pyridyl, pyrimidinyl, triazinyl, phosphinyl, nitrile, nitro, oxazolyl, quinoxalinyl, thiazolyl, quinolinyl, imidazole, phenylpyrimidine, boroheterocyclyl, sulfone, and derivatives thereof.
Alternatively, ring a and ring B are each independently one of the following structural formulas:
the structure of the A, B ring is not limited to the above structure, and a specific suitable structure may be selected according to the actual situation.
Alternatively, when n in the general formula (I) is 0, the structural general formula is shown as the following general formula (II):
in this embodiment, the compounds having the general formula (ii) may include the following compounds 1 to 3:
the structure of the compound of the general formula (ii) is not limited to the above structure.
Alternatively, when X in formula (I) is a direct bond, the general structural formula is shown as formula (III):
in the present embodiment, the compound having the general formula (iii) may include the following compounds 4 to 60:
the structure of the compound of the general formula (iii) is not limited to the above structure.
Alternatively, when N is 1 and X is one of O, S, C and N, the structural formula is shown as the following formula (IV):
in this example, the compounds having the general formula (iv) may include the following compounds 61 to 87:
the structure of the compound of the general formula (iv) is not limited to the above structure.
Specific production methods of spiro compounds of the present application will be described in detail below by taking a plurality of synthesis examples as examples, but the production methods of the present application are not limited to these synthesis examples.
Various chemicals used in the application, such as basic chemical raw materials of 4-bromophenanthrene, tetrahydrofuran, butyl lithium, acetic acid, sulfuric acid, dioxane, potassium acetate, potassium carbonate aqueous solution, anhydrous magnesium sulfate and the like, can be purchased in domestic chemical product markets.
Synthesis example 1
Synthesis of compound E1:
step 1: intermediate 1 was synthesized as follows:
in a three-neck flask, 70 millimoles (mmol) of compound 1a (4-bromophenanthrene) are dissolved in 200mL of Tetrahydrofuran (THF) and cooled to-78 ℃; slowly dropwise adding 64mmol of butyl lithium (n-BuLi) at the temperature of not more than-75 ℃, and heating to room temperature for reacting for 1h after dropwise adding; adding 200mL of THF solution dissolved with 60mmol of compound 1b into a reaction bottle, and refluxing the mixed solution for reaction for 3 h; after the reaction was detected by TLC (Thin Layer Chromatography), extraction was performed with ethyl acetate; concentration after extraction was complete gave compound 1 c.
Adding 50mmol of the compound 1c into 200mL of acetic acid, stirring at 80 ℃, and dripping 1-2 drops of sulfuric acid; and (3) after refluxing for 3h, cooling the temperature to normal temperature, after the reaction is finished, extracting by using dichloromethane, and separating to obtain a compound 1 d.
Completely dissolving the 38mmo compound 1d and 40.5mmol compound 1e in 170mL Dioxane (Dioxane), adding 110.5mmol potassium acetate, heating and stirring, cooling to room temperature, removing potassium carbonate solution, and filtering to remove potassium acetate; solidifying the filtrate with ethanol and filtering; the white solid was washed with ethanol 2 times, respectively, to give intermediate 1 in 82% yield.
Step 2: compound E1 was synthesized as follows:
after completely dissolving 15mmol of intermediate 1 and 13mmol of compound A1 in 300ml of tetrahydrofuran in a 500ml round-bottom flask under nitrogen, 100ml of 2M aqueous potassium carbonate solution was added; after adding 0.39mmol of tetrakis (triphenylphosphine) palladium (Pd (PPh3)4), the mixture was stirred with heating for 4 hours; cooling to normal temperature, removing water layer, drying with anhydrous magnesium sulfate, and concentrating under reduced pressure; recrystallization from 250ml of ethyl acetate gave compound E1 in 76% yield.
Synthesis example 2
Synthesis of compound E2:
step 1: intermediate 2 was synthesized as follows:
the synthesis procedure was the same as for intermediate 1 except that compound 1b was changed to compound 2b and the other reagents were unchanged to give intermediate 2 in 72.3% yield.
Step 2: compound E1 was synthesized as follows:
after 18.9mmol of intermediate 2 and 16.47mmol of compound B1 were completely dissolved in 150ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 100ml of 2M aqueous potassium carbonate solution was added; adding 0.48mmol of tetrakis (triphenylphosphine) palladium, heating and stirring for 4 hours; the temperature was lowered to normal temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration under reduced pressure was performed, followed by recrystallization from 250ml of ethyl acetate to obtain compound E2 with a yield of 75.8%.
Synthesis example 3
Synthesis of compound E3:
step 1: intermediate 3 was synthesized as follows:
the synthesis procedure was the same as for intermediate 1 except that compound 1b was changed to 3b and the other reagents were unchanged to give intermediate 3 in 79.5% yield.
Step 2: compound E3 was synthesized as follows:
after 18.9mmol of intermediate 3 and 16.47mmol of compound C1 were completely dissolved in 150ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen, 100ml of 2M aqueous potassium carbonate solution was added, 0.48mmol of tetrakis (triphenylphosphine) palladium was added, and the mixture was stirred under heating for 4 hours; after the temperature was decreased to normal temperature and the aqueous layer was removed and dried over anhydrous magnesium sulfate, concentration under reduced pressure and recrystallization from 250ml of ethyl acetate were carried out to obtain compound E2 in a yield of 75.8%.
Synthesis example 4
Synthesis of compound E4:
step 1: intermediate 4 was synthesized as follows:
the synthesis procedure was the same as for intermediate 1 except that compound 1b was changed to 4b and the other reagents were unchanged to give intermediate 4 in 83.6% yield.
Step 2: compound E4 was synthesized as follows:
after 16.7mmol of intermediate 4 and 13.26mmol of compound D1 were completely dissolved in 150ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 100ml of a 2M aqueous potassium carbonate solution was added, 0.41mmol of tetrakis (triphenylphosphine) palladium was added, and the mixture was stirred under heating for 4 hours; the temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration under reduced pressure was performed, followed by recrystallization from 250ml of ethyl acetate to obtain compound E4 with a yield of 81.3%.
As shown in the following table 1, the spatial configuration of the spiro compounds of the general formula (II), the general formula (III) and the general formula (IV) is simulated by using molecular simulation software, which is specifically as follows:
TABLE 1
As can be seen from table 1, the spiro compound of the present application belongs to an orthogonal spatial configuration, and the electron transport material containing the spiro compound is utilized to make molecules have a better spatial structure, reduce the intermolecular van der waals force, effectively prevent crystallization of the electron transport material, and improve the light emitting performance of the light emitting device.
As shown in table 2 below, the electron cloud distribution of the spiro compounds of general formula (ii), general formula (iii) and general formula (iv) was simulated using molecular simulation software as follows:
TABLE 2
As can be seen from table 2, SP3 hybridization of a central C atom in the spiro compound can break conjugation of molecules, so that energy levels of HOMO and LUMO are distributed in an upper part and a lower part, which is beneficial to regulation of an energy level of an electron transport material and prevention of triplet level reduction, and can realize matching with an adjacent functional layer, and meanwhile, the spiro compound adopts an asymmetric spiro structure, so that symmetry of molecules can be reduced, and film-forming property of molecules can be improved.
As shown in table 3 below, the glass transition temperature (Tg) of the spiro compounds of the general formula (ii), the general formula (iii) and the general formula (iv) was measured by using a DSC differential scanning calorimeter as a measuring instrument, nitrogen as a measuring atmosphere, a temperature rise rate of 10 ℃/min, and a temperature range of 50 to 380 ℃, as follows:
TABLE 3
As can be seen from table 3, the spiro compound has a rigid three-dimensional structure, and the electron transport material containing the spiro compound has a higher glass transition temperature, which is beneficial to improving the thermodynamic stability of the electron transport material; when the evaporation process is carried out, the electronic transmission material is not cracked and changed, so that the method has better moldability and prolongs the service life of the electronic transmission material. The electronic transmission material with high glass transition temperature is used in the luminescent device, so that the performance of the device can be obviously improved.
Based on the same inventive concept, embodiments of the present application provide an electron transport material including the spiro compound provided in the above embodiments.
In this embodiment, the electron transport material includes the above mentioned spiro compound, and the beneficial effects of the electron transport material include the beneficial effects of the above mentioned spiro compound, which are not described herein again.
Based on the same inventive concept, the present embodiment provides a light emitting device 100, as shown in fig. 1, including a first electrode 1, a light emitting functional layer 2, and a second electrode 4, which are sequentially stacked, wherein the light emitting functional layer 2 includes an electron transport layer 26, and the electron transport layer 26 includes the electron transport material provided in the above embodiment.
In this embodiment, the first electrode 1 is an anode, and may be a transparent oxide ITO or IZO, or may be a composite electrode formed by ITO/Ag/ITO, Ag/IZO, CNT/ITO, CNT/IZO, GO/ITO, GO/IZO, etc.; the second electrode 4 is a cathode. The electron transport material in the light emitting device 100 introduces a spiro compound, so that the electron transport material has a high triplet energy level, and can prevent excitons generated in the light emitting layer 24 from diffusing to the electron transport layer 26, thereby improving the light emitting efficiency of the light emitting device 100; the introduction of the spiro compound into the electron transport material can improve the injectability of the electron transport material, thereby reducing the driving voltage of the light emitting device 100; the electron transport material has a high glass transition temperature, and is favorable for improving the stability of the electron transport material, so that the luminous efficiency of the light-emitting device 100 can be improved, and the service life of the light-emitting device 100 can be prolonged.
Optionally, the light-emitting functional layer 2 further includes a hole blocking layer 25 disposed on a side of the electron transport layer 26 close to the first electrode 1, and the hole blocking layer 25 includes the electron transport material provided in the above embodiment.
Optionally, the light emitting device 100 further comprises a substrate 3 disposed on a side of the first electrode 1 away from the second electrode 4, and the substrate 3 may be a transparent rigid or flexible substrate 3 material, such as glass, polyimide, or the like.
Optionally, the light-emitting functional layer 2 further comprises a hole injection layer 21, a hole transport layer 22, an electron blocking layer 23 and a light-emitting layer 24 which are arranged on the first electrode 1 close to the hole blocking layer 25 in a stacked manner; the light-emitting functional layer 2 further includes an electron injection layer 27 disposed on the side of the electron transport layer 26 remote from the hole blocking layer 25.
In the present embodiment, the hole injection layer 21 may be an inorganic oxide such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, or the like, or may be a dopant of a strong electron-withdrawing system such as F4TCNQ, HATCN, or the like, or may be P-doped in the hole transport material, and the thickness of the hole injection layer 21 may be 5nm (nanometers) to 30nm (nanometers). The hole transport layer 22 is made of an aromatic amine or carbazole material, such as NPB, TPD, BAFLP, DFLDPBi, etc., and the thickness of the hole transport layer 22 may be 100nm to 2000 nm. The electron blocking layer 23, i.e., the luminescence auxiliary layer, has a hole transport property, and may be a red luminescence auxiliary layer, a green luminescence auxiliary layer, or a blue luminescence auxiliary layer, the material of the luminescence auxiliary layer may be arylamine or carbazole materials, such as CBP, PCzPA, or the like, and the thickness of the electron blocking layer 23 may be 5nm to 100 nm.
The light-emitting layer 24 may be a phosphorescent host and a red phosphorescent dopant, a phosphorescent host and a green phosphorescent dopant, or a fluorescent host and a fluorescent dopant, and the host material of the light-emitting layer 24 may include one material or a mixture of two or more materials, wherein the host material of the blue light-emitting layer 24 may be selected from anthracene derivatives ADN, MADN, and the like, and the guest material may be a pyrene derivative, a fluorene derivative, a perylene derivative, a styryl amine derivative, a metal complex, and the like, such as TBPe, BDAVBi, DPAVBi, FIrpic, and the like; the host material of the green light emitting layer 24 can be selected from coumarin dyes, quinacridone copper derivatives, polycyclic aromatic hydrocarbons, diamine anthracene derivatives, carbazole derivatives, such as DMQA, BA-NPB, Alq3, etc., and the guest material can be metal complexes, such as Ir (ppy)3, Ir (ppy)2(acac), etc.; the red light emitting host material can be selected from DCM series materials such as DCM, DCJTB, DCJTI, etc., the guest material can be a metal complex such as Ir (piq)2(acac), PtOEP, Ir (btp)2(acac), etc., and the thickness of the light emitting layer 24 can be 20nm to 100 nm.
The thickness of the hole-blocking layer 25 may be 5nm to 100nm, the thickness of the electron-transporting layer 26 may be 20nm to 100nm, and the hole-blocking layer 25 and the electron-transporting layer 26 independently include aromatic heterocyclic compounds such as imidazole derivatives such as benzimidazole derivatives, imidazopyridine derivatives, and benzimidazolophthalridine derivatives, and oxazine derivatives such as pyrimidine derivatives and triazine derivatives, and also include compounds containing a nitrogen-containing six-membered ring structure such as quinoline derivatives, isoquinoline derivatives, and phenanthroline derivatives, and may also include compounds having a substituent of the phosphine oxide series on the heterocyclic ring, for example: OXD-7, TAZ, p-etaz), BPhen, BCP, electron transport materials of the present application, and the like. The thickness of the electron injection layer 27 may be 1nm to 10nm, and the material of the electron injection layer 27 includes alkali metal or metal, such as LiF, Yb, Mg, Ca, or a compound thereof, etc.
Taking fig. 1 as an example, the structure of the light emitting device 100 is: substrate 3 (glass plate)/first electrode 1 (ITO)/hole injection layer 21(10 nm)/hole transport layer 22(100 nm)/electron blocking layer 23(35 nm)/light emitting layer 24(20 nm)/hole blocking layer 25(5 nm)/electron transport layer 26(30 nm)/electron injection layer 27(1 nm)/second electrode 4(100 nm).
The following describes the fabrication process of the light emitting device 100 in fig. 1 in detail:
the substrate 3 (glass plate) provided with the first electrode 1(ITO) is subjected to ultrasonic treatment in a cleaning agent, washed in deionized water, ultrasonically degreased in an acetone-ethanol mixed solvent, and baked in a clean environment until water is completely removed.
Placing the glass plate with ITO in a vacuum chamber, vacuumizing to 1 × 10-5～1×10-6A hole injection layer 21 is formed by vacuum-depositing a hole injection material on the side of the ITO remote from the glass plate.
A hole transport material is evaporated on the side of the hole injection layer 21 remote from the ITO to form a hole transport layer 22.
An electron blocking material is vacuum-deposited on the side of the hole transport layer 22 remote from the hole injection layer 21, to form an electron blocking layer 23.
And (3) performing vacuum evaporation on the side, away from the hole transport layer 22, of the electron blocking layer 23 to form a light emitting layer 24, wherein the light emitting material comprises a host material and a guest material, and the weight ratio of the host material to the guest material is 97: 3.
a hole blocking material is vacuum-evaporated on the side of the light emitting layer 24 remote from the electron blocking layer 23 to form a hole blocking layer 25.
An electron transport material is vacuum-evaporated on the side of the hole blocking layer 25 remote from the light emitting layer 24 to form an electron transport layer 26.
An inorganic material (LiF) having a thickness of 1nm was vacuum-deposited on the side of the electron transport layer 26 remote from the hole blocking layer 25 as an electron injecting material, thereby forming an electron injecting layer 27.
An Al layer is plated on the electron injection layer 27 away from the electron transport layer 26 as a cathode.
As shown in table 4 below, are compounds among the materials used for the hole injection layer 21, the hole transport layer 22, the electron blocking layer 23, the light-emitting layer 24, the hole blocking layer 25, and the electron transport layer 26.
TABLE 4
The driving voltage and the luminous efficiency of five light emitting devices were measured at a fixed current density at 15mA/cm2The light-emitting device of example 1, in which the electron transport material included compound E1; the electron transport layer material in the light-emitting device of example 2 includes a compound E2; the electron transporting material in the light-emitting device of embodiment 3 includes a compound E3; the electron transporting material in the light-emitting device of embodiment 4 includes a compound E4; the electron transporting material in the light-emitting device of embodiment 5 includes a compoundAn object 83; the electron transport material in the light emitting device of example 6 included the comparative compound, and the test results are shown in table 5.
TABLE 5
As can be seen from table 5, the driving voltages of examples 1 to 5 are lower than those of example 6, because the compound E1, the compound E2, the compound E3, the compound E4, and the compound 83 contained in the electron transport layer are hybridized with SP3 of the central C atom, which can break the conjugation of molecules, facilitate the separation of HOMO and LUMO, facilitate the adjustment of energy levels, facilitate the matching of adjacent functional layers, and further the light emitting device has a lower driving voltage.
It can also be seen from table 5 that the light emitting efficiency and the service life of embodiments 1 to 5 are both higher than those of embodiment 6, because the compound E1, the compound E2, the compound E3, the compound E4, and the compound 83 contained in the electron transport layer have orthogonal spatial configurations, which can reduce intermolecular van der waals force, and is beneficial to preventing crystallization of the electron transport material, thereby improving the display performance of the light emitting device, and the compound E1, the compound E2, the compound E3, the compound E4, and the compound 83 have rigid structures, so that the electron transport material has a higher glass transition temperature, and is beneficial to improving the stability of the electron transport material, thereby improving the light emitting efficiency and the service life of the light emitting device.
By applying the embodiment of the application, at least the following beneficial effects can be realized:
1. the spiro compound provided by the embodiment of the application has an orthogonal spatial configuration, so that intermolecular van der waals force can be reduced, the electronic transmission material containing the spiro compound is prevented from crystallizing, and the display performance of a light-emitting device can be improved.
2. The spiro compound provided by the embodiment of the application has a high triplet energy level, and the electron transport material containing the spiro compound has a high triplet energy level, so that excitons generated in the light emitting layer can be prevented from diffusing to the electron transport layer, and the light emitting efficiency of the light emitting device is improved.
3. The SP3 hybridization of the central C atom in the spiro compound provided by the embodiment of the application can break the conjugation of molecules, so that the energy levels of HOMO and LUMO are distributed at the upper part and the lower part, and the regulation and control of the energy level of an electron transport material are facilitated, and the reduction of a triplet level is facilitated.
4. The spiro compound provided by the embodiment of the application has a rigid structure, so that an electron transmission material containing the spiro compound has higher glass transition temperature, the stability of the electron transmission material is favorably improved, and meanwhile, the spiro compound adopts an asymmetric spiro structure, so that the symmetry of molecules can be reduced, and the film-forming property of the molecules is favorably improved.
Those of skill in the art will appreciate that the various operations, methods, steps in the processes, acts, or solutions discussed in this application can be interchanged, modified, combined, or eliminated. Further, other steps, measures, or schemes in various operations, methods, or flows that have been discussed in this application can be alternated, altered, rearranged, broken down, combined, or deleted. Further, steps, measures, schemes in the prior art having various operations, methods, procedures disclosed in the present application may also be alternated, modified, rearranged, decomposed, combined, or deleted.
The terms "first", "second" and "first" are used for descriptive purposes only and are not to be construed as indicating or implying relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defined as "first" or "second" may explicitly or implicitly include one or more of that feature. In the description of the present application, "a plurality" means two or more unless otherwise specified.
In the description herein, particular features, structures, materials, or characteristics may be combined in any suitable manner in any one or more embodiments or examples.
The foregoing is only a part of the embodiments of the present application, and it should be noted that it is within the scope of the embodiments of the present application that other similar implementation means based on the technical idea of the present application can be adopted by those skilled in the art without departing from the technical idea of the present application.
Claims (10)
1. A spiro compound, wherein the structural formula of the spiro compound is shown as the following general formula (I):
in the general formula (I), R1 to R8 each independently include a substituted or unsubstituted design group; ar1 and Ar2 at least contain one electron-withdrawing group and cannot be hydrogen at the same time; each of the a ring and the B ring independently includes a substituted or unsubstituted monocyclic or polycyclic aromatic ring, or includes a substituted or unsubstituted phenyl, naphthyl, phenanthrene, fluoranthene, fluorene, thiophene, or furyl group; n is 0 or 1; in the case where N is 1, X is one of a direct bond, O, S, C, and N, wherein when X is a direct bond, both ring a and ring B cannot be unsubstituted phenyl.
2. The spiro compound according to claim 1, wherein when n is 0 in the general formula (i), the structural formula is represented by the following general formula (ii):
3. the spiro compound according to claim 1, wherein when X in the general formula (i) is a direct bond, the structural general formula is represented by the following general formula (iii):
4. the spiro compound according to claim 1, wherein when N in the general formula (i) is 1 and X is one of O, S, C and N, the structural formula is represented by the following general formula (iv):
5. the spiro compound according to claim 1, comprising at least one of:
the electron-withdrawing group is independently one of pyridyl, pyrimidyl, triazinyl, phosphinyl, nitrile, nitro, oxazolyl, quinoxalinyl, thiazolyl, quinolyl, imidazole, phenylpyrimidine, oxaboronyl, sulfone and derivatives thereof;
ar1 and Ar2 are each independently one of the following: hydrogen, deuterium, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an alkenyl group, a silyl group, a boron group, an amine group, an arylphosphino group, a phosphino group, an aryl group, a heteroaryl group, or adjacent groups may be bonded to each other to form a ring.
6. The spiro compound according to claim 1, wherein each of the R1-R8 design groups is independently one of: hydrogen, deuterium, cyano, halogen, nitro, hydroxyl, carbonyl, ester, imide, amide, alkyl, cycloalkyl, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, alkenyl, silyl, boron, amine, phosphine oxide, aryl, heteroaryl, pyridyl, pyrimidinyl, triazinyl, phosphinyl, nitrile, nitro, oxazolyl, quinoxalinyl, thiazolyl, quinolinyl, imidazole, phenylpyrimidine, boroheterocyclyl, sulfone, and derivatives thereof.
7. The spiro compound of claim 1, wherein said a ring and said B ring are each independently one of the following structural formulas:
8. an electron transport material, comprising: the spiro compound according to any one of claims 1 to 6.
9. A light-emitting device comprising a first electrode, a light-emitting functional layer and a second electrode which are stacked in this order, the light-emitting functional layer comprising an electron transport layer, the electron transport layer comprising the electron transport material according to claim 8.
10. A light-emitting device according to claim 9, wherein the light-emitting functional layer further comprises a hole-blocking layer provided on a side of the electron-transporting layer adjacent to the first electrode, the hole-blocking layer comprising the electron-transporting material according to claim 8.
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| CN115677767A (en) * | 2022-10-26 | 2023-02-03 | 京东方科技集团股份有限公司 | A kind of organic electron transport material and organic electroluminescent device |
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| CN115677767A (en) * | 2022-10-26 | 2023-02-03 | 京东方科技集团股份有限公司 | A kind of organic electron transport material and organic electroluminescent device |
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| CN114591257B (en) | 2024-06-14 |
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