CN117185990B - Compound and organic electroluminescent device comprising same - Google Patents
Compound and organic electroluminescent device comprising same Download PDFInfo
- Publication number
- CN117185990B CN117185990B CN202311465792.5A CN202311465792A CN117185990B CN 117185990 B CN117185990 B CN 117185990B CN 202311465792 A CN202311465792 A CN 202311465792A CN 117185990 B CN117185990 B CN 117185990B
- Authority
- CN
- China
- Prior art keywords
- synthesis
- compound
- raw materials
- organic electroluminescent
- electroluminescent device
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 41
- 230000015572 biosynthetic process Effects 0.000 description 56
- 238000003786 synthesis reaction Methods 0.000 description 56
- 239000000543 intermediate Substances 0.000 description 40
- 239000010410 layer Substances 0.000 description 32
- 239000002994 raw material Substances 0.000 description 32
- 239000000463 material Substances 0.000 description 19
- 238000000605 extraction Methods 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000001308 synthesis method Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000005253 cladding Methods 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- DIRRKLFMHQUJCM-UHFFFAOYSA-N (2-aminophenyl)boronic acid Chemical compound NC1=CC=CC=C1B(O)O DIRRKLFMHQUJCM-UHFFFAOYSA-N 0.000 description 2
- PLVCYMZAEQRYHJ-UHFFFAOYSA-N (2-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Br PLVCYMZAEQRYHJ-UHFFFAOYSA-N 0.000 description 2
- RRCMGJCFMJBHQC-UHFFFAOYSA-N (2-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Cl RRCMGJCFMJBHQC-UHFFFAOYSA-N 0.000 description 2
- XEKTVXADUPBFOA-UHFFFAOYSA-N 1-bromo-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(Br)C(F)=C1F XEKTVXADUPBFOA-UHFFFAOYSA-N 0.000 description 2
- DONVNRFILRLHJB-UHFFFAOYSA-N 1-bromo-2,3,5,6-tetrafluoro-4-(trifluoromethyl)benzene Chemical compound FC1=C(F)C(C(F)(F)F)=C(F)C(F)=C1Br DONVNRFILRLHJB-UHFFFAOYSA-N 0.000 description 2
- CSVCVIHEBDJTCJ-UHFFFAOYSA-N 1-bromo-3,5-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Br)=CC(C(F)(F)F)=C1 CSVCVIHEBDJTCJ-UHFFFAOYSA-N 0.000 description 2
- XHCAGOVGSDHHNP-UHFFFAOYSA-N 1-bromo-4-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=C(Br)C=C1 XHCAGOVGSDHHNP-UHFFFAOYSA-N 0.000 description 2
- KGCDGLXSBHJAHZ-UHFFFAOYSA-N 1-chloro-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(Cl)C(F)=C1F KGCDGLXSBHJAHZ-UHFFFAOYSA-N 0.000 description 2
- OXMBWPJFVUPOFO-UHFFFAOYSA-N 1-chloro-3,5-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=CC(C(F)(F)F)=C1 OXMBWPJFVUPOFO-UHFFFAOYSA-N 0.000 description 2
- MYMYVYZLMUEVED-UHFFFAOYSA-N 2-bromo-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1Br MYMYVYZLMUEVED-UHFFFAOYSA-N 0.000 description 2
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 2
- IVBVKTPDEWDNRW-UHFFFAOYSA-N 4-bromooxane Chemical compound BrC1CCOCC1 IVBVKTPDEWDNRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- -1 diamine aromatic compound Chemical class 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to the technical field of organic light-emitting display, in particular to a compound and an organic electroluminescent device containing the same. The invention provides a compound which has a structural general formula (1-1). The compound provided by the invention has low refractive index, and can improve the luminous performance of the device when being applied to an organic electroluminescent device.
Description
Technical Field
The invention relates to the technical field of organic light-emitting display, in particular to a compound and an organic electroluminescent device containing the same.
Background
The main function of the light extraction material is to improve the light extraction efficiency of the light emitting element. The light extraction material forms an organic coating layer on the transparent metal electrode at the upper part of the organic electroluminescent device, so as to adjust the optical interference distance, inhibit extinction and the like caused by external light reflection and surface plasma movement, and improve the light extraction efficiency of the luminescent device.
There are two approaches to increase the light extraction efficiency by increasing the cladding, increasing the refractive index of a single cladding or using a dual cladding structure. However, the increase in refractive index of the single cladding layer is limited; the dual cladding structure may further improve light emission efficiency by inserting a low refractive index material between the high refractive index material and the light emitting layer material, thereby forming a second resonant cavity.
Aromatic compounds are generally used as low-refractive-index materials in the prior art, but the refractive index is generally higher, and the difference between the materials and common high-refractive-index materials is difficult to reach more than 0.3.
Carbazole derivatives, benzimidazole derivatives, triazole derivatives, and the like have also been proposed in the prior art as low refractive index materials. Among them, three stars in 2017 (CN 107369771B) proposed a fluorine-containing oligomer; in 2018, sea spectrum Runs (CN 109037483B) proposed a diamine aromatic compound; non-aromatic amine fluorochemicals are proposed in LAPTO (KR 102252493B1, KR102261704B1, WO2021230512A1, WO2021230511A1, KR102274482B1, WO2021230513A 1) from 2019 to 2021; the east-beauty tip material (CN 113260605 a) in 2020 proposed aromatic amine fluorine-containing compounds; the semiconductor energy institute of 2021 (WO 2021260494A1, WO2022023864 A1) proposed the use of fluorene-containing low-fold materials.
However, the refractive index of the above-mentioned compound in the prior art is not low enough, so that development of a material having a lower refractive index for a low-refractive-index material is highly desired.
Disclosure of Invention
In order to solve the technical problems in the prior art, the invention provides a compound and an organic electroluminescent device comprising the same.
One of the purposes of the present invention is to provide a compound having a general structural formula represented by the formula (1-1):
，
wherein R1, R2 and R3 are independently selected from H, F, CF 3 C with or without substituents 6 ~C 15 Aryl, substituted or unsubstituted C 5 ~C 13 Heteroaryl, substituted or unsubstituted C 5 ~C 10 Cycloalkyl, substituted or unsubstitutedSubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 5 Any one of the heteroatom-containing cycloalkyl groups;
m and n are each independently integers of 0 to 5;
the substituent groups are selected from F, CF 3 、C 1 ~C 10 Alkyl, C of (2) 6 ~C 15 Aryl, C of (2) 5 ~C 13 Heteroaryl, C 5 ~C 10 Cycloalkyl or C of (C) 2 ~C 5 A heteroatom-containing cycloalkyl group;
the heteroatom is O, S or N.
Further, m and n are each independently preferably 0, 1, 2, 5;
more preferably, m and n are each independently 1, 2, or 5.
Further, the compound is selected from the following structures:
。
further, R11 to R17, R21 to R24, R31 to R39, R310, R311, R41 to R45, R51 to R58, R61 to R68, R71 to R73 are each independently selected from H, CF 3 F, tert-butyl, methyl or a group of 4-1 to 4-52, preferably F, CF 3 T-butyl:
。
further, the substituted or unsubstituted C 6 ~C 15 Is selected from the group shown in 4-1 to 4-30, preferably any one of the groups shown in 4-1 to 4-4, 4-9, 4-11, 4-22, 4-25 to 4-29).
。
Further, the substituted or unsubstituted C 5 ~C 13 The heteroaryl group of (2) is selected from any one of the groups shown in 4-31 to 4-43, preferably 4-33:
。
further, the alkyl group is selected from any one of methyl, tert-butyl, ethyl, propyl and isopropyl, preferably methyl and tert-butyl.
Further, the substituted or unsubstituted C 5 ~C 10 Is selected from any one of the groups shown in 4-44 to 4-46, preferably 4-45 and 4-46:
。
further, the substituted or unsubstituted C 2 ~C 5 The heteroatom-containing cycloalkyl group of (2) is selected from any one of the groups shown in 4-47 to 4-52, preferably 4-48 and 4-50:
。
further, the compound is selected from the following structural formulas:
。
another object of the present invention is to provide an organic electroluminescent device, which includes a light emitting layer, a first light extraction layer and a second light extraction layer, wherein the first light extraction layer is located between the second light extraction layer and the light emitting layer, and the first light extraction layer includes the above compound.
Compared with the prior art, the invention has the following technical effects:
the compound has high steric hindrance and lower refractive index, is used for a light extraction layer material with low refractive index in an organic electroluminescent device with a double-layer light extraction layer, and can improve the luminous efficiency of the organic electroluminescent device and obtain a high-color purity device.
Drawings
Fig. 1 shows a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present invention;
reference numerals:
1. an anode; 2. a hole injection layer; 3. a hole transport layer; 4. an electron blocking layer; 5. a light emitting layer; 6. a hole blocking layer; 7. an electron transport layer; 8. an electron injection layer; 9. a cathode; 10. a first light extraction layer; 11. and a second light extraction layer.
Detailed Description
Further advantages and effects of the present invention will become apparent to those skilled in the art from the disclosure of the present specification, by describing the embodiments of the present invention with specific examples. While the description of the invention will be described in connection with the preferred embodiments, it is not intended to limit the inventive features to the implementation. Rather, the purpose of the invention described in connection with the embodiments is to cover other alternatives or modifications, which may be extended by the claims based on the invention. The following description contains many specific details for the purpose of providing a thorough understanding of the present invention. The invention may be practiced without these specific details. Furthermore, some specific details are omitted from the description in order to avoid obscuring the invention. It should be noted that, without conflict, the embodiments of the present invention and features of the embodiments may be combined with each other.
The method of producing the organic electroluminescent device of the present invention is not particularly limited, and any method known in the art may be employed. The organic electroluminescent device of the invention comprises an anode 1 (100 nm-150 nm), a hole injection layer 2 (5 nm-20 nm), a hole transport layer 3 (80 nm-140 nm), a cathode and an anode on a substrate in sequence,
An electron blocking layer 4 (5 nm-15 nm), a light emitting layer 5 (20 nm-45 nm), a hole blocking layer 6 (5 nm-15 nm), an electron transport layer 7 (30 nm-40 nm), an electron injection layer 8 (0.3 nm-1 nm), a cathode 9 (10 nm-16 nm), a first light extraction layer 10 (low-refraction layer 5nm-50 nm), and a second light extraction layer 11 (high-refraction layer 50nm-90 nm).
The present invention is illustrated by the following examples in the materials synthesis section, but the present invention is not limited to the fluorochemicals and synthesis methods illustrated in these examples.
Unless otherwise indicated, the materials and methods used in the examples and comparative examples were all obtained or used according to techniques well known to those skilled in the art.
Various raw materials according to the present invention are purchased from companies such as aladine, and various palladium catalysts are purchased from companies such as grid Lin Kaimo.
HPLC spectra were determined using an LC-20AXR high performance liquid chromatograph.
The raw material information for the preparation of the compounds is as follows:
a-0: chinese name, 3, 5-bistrifluoromethyl bromobenzene; CAS No. 328-70-1.
A-1: chinese name, 2-bromophenyl boronic acid; CAS No. 244205-40-1.
A-2: chinese name, 2-chlorophenylboronic acid; CAS No. 3900-89-8.
A-3: chinese name, bromopentafluorobenzene; CAS No. 344-04-7.
A-4: chinese name, 2-aminophenylboronic acid; CAS No. 5570-18-3.
A-5: chinese name, 2, 6-dimethyl bromobenzene; CAS No. 576-22-7.
A-6: chinese name, 3-bromopyridine; CAS No. 626-55-1.
A-7: chinese name, chloropentafluorobenzene; CAS No. 344-07-0.
A-8: chinese name, 4-tert-butylbromobenzene; CAS No. 3972-65-4.
A-9: chinese name, 3, 5-bistrifluoromethyl chlorobenzene; CAS No. 328-72-3.
A-10: chinese name, 4-bromotetrahydropyran; CAS No. 25637-16-5.
A-11: chinese name, 4-bromo-2, 3,5, 6-tetrafluorobenzotrifluoride; CAS No. 17823-46-0.
A-12: chinese name, bromobenzene; CAS No. 108-86-1.
A-13: chinese name, bromocyclohexane; CAS number 108-85-0.
The structural information of the raw materials used for the preparation of the compounds is as follows:
all of the above materials are chemical materials well known to those skilled in the chemical arts.
Synthesis example 1: synthesis of Compound 2-1-2
(1) Preparation of intermediate 2-1-2-M0:
into a reaction flask were charged 100mmol of A-0, 100mmol of A-1, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) Reacting at 120deg.C for 12 hr, cooling to room temperature, adding water, concentrating the organic phase to obtain white solid, filtering, washing with water, recrystallizing with toluene to obtain white powder 2-1-2-M0, wherein Pd (PPh) 3 ) 4 The addition amount of (C) is 1mol% of A-0;
(2) Preparation of intermediates 2-1-2-M1, 2-1-2-M2, 2-1-2-M3:
the preparation methods of the intermediates 2-1-2-M1, 2-1-2-M2 and 2-1-2-M3 are the same as the preparation method of 2-1-2-M0, and are different in that raw materials are selected, and the synthetic raw materials of the intermediates 2-1-2-M1, 2-1-2-M2 and 2-1-2-M3 are respectively as follows: 2-1-2-M0 and A-2, A-3 and A-4, A-5 and A-2;
(3) Preparation of intermediate 2-1-2-M4:
into a reaction flask were charged 100mmol of 2-1-2-M1, 100mmol of 2-1-2-M2, 28.83g of sodium tert-butoxide (300 mmol) and 800ml of xylene, and 1mol% of palladium bis dibenzylidene acetonate (Pd (dba) 2 ) Reacting at 120deg.C for 12 hr, stopping the reaction, cooling to room temperature, adding water, filtering, washing with water, and recrystallizing and purifying the obtained solid with toluene to obtain white powder 2-1-2-M4, wherein Pd (dba) 2 The addition amount of (C) is 1mol% of 2-1-2-M1;
(4) Preparation of final product 2-1-2:
into a reaction flask were charged 100mmol of 2-1-2-M3, 100mmol of 2-1-2-M4, 28.83g of sodium tert-butoxide (300 mmol) and 800ml of xylene, and 1mol% of Pd (dba) was added 2 Reacting at 120deg.C for 12 hr, stopping the reaction, cooling to room temperature, adding water, filtering, washing with water, and recrystallizing and purifying the obtained solid with toluene to obtain white powder 2-1-2, wherein Pd (dba) 2 The amount of (C) added is 1mol% of 2-1-2-M3.
The HPLC purity of the prepared compound 2-1-2 was 99.9%.
1H NMR (400 MHz, Chloroform-d) δ 8.10 (s, 1H), 7.91 (d, J = 6.4 Hz, 2H), 7.71 (s, 1H), 7.62 (m, 2H), 7.52 (m, 4H), 7.33 (m, 9H), 7.16 (s, 1H), 7.07 (m, 2H), 2.23 (d, J = 7.2 Hz, 6H).
Synthesis example 2: synthesis of Compound 2-2-1
(1) Synthesis of intermediate 2-2-1-M0:
the synthesis step of the intermediate 2-2-1-M0 refers to the synthesis of 2-1-2-M0, and is different in that raw materials are selected, and the synthetic raw materials of the intermediate 2-2-1-M0 are A-13 and A-4;
(2) Synthesis of final product 2-2-1:
into a reaction flask were charged 100mmol of 2-2-1-M0, 200mmol of 2-1-2-M0, 200mmol of sodium t-butoxide, 1mol% of tribenzylidene acetone dipalladium (Pd) 2 (dba) 3 ) 4mol% of 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (X-PHOS), reflux reaction, stopping the reaction after the reaction, cooling the reactant to room temperature, adding water, concentrating an organic phase to obtain a white solid, filtering, washing the white solid with water, and recrystallizing and purifying the obtained solid with toluene to obtain white powder 2-2-1, wherein Pd 2 (dba) 3 The amount of the catalyst to be added was 1mol% of 2-2-1-M0, and the amount of the X-PHOS to be added was 4mol% of 2-2-1-M0.
The HPLC purity of the prepared compound 2-2-1 was 99.9%.
1H NMR (400 MHz, Chloroform-d) δ 8.09 (t, J = 6.4 Hz, 2H), 7.90 (d, J =6.4 Hz, 4H), 7.71 (m, 2H), 7.31 ~7.21 (m, 7H), 7.16 (s, 1H), 7.00 (s, 1H), 2.92 (s, 1H), 1.65 (m, 11H).
Synthesis example 3: synthesis of Compound 2-3-5
(1) Synthesis of intermediates 2-3-5-M0, 2-3-5-M1, 2-3-5-M2:
the synthesis of intermediates 2-3-5-M0, 2-3-5-M1 and 2-3-5-M2 refers to the synthesis of intermediates 2-1-2-M0, and is different in the selection of raw materials, and the synthesis raw materials of intermediates 2-3-5-M0, 2-3-5-M1 and 2-3-5-M2 are respectively as follows: a-6 and A-1; a-1 and 2-3-5-M0;2-3-5-M1 and A-2;
(2) Synthesis of intermediate 2-3-5-M3:
the synthesis of the intermediate 2-3-5-M3 is based on the synthesis of the intermediate 2-1-2-M4, and is different in the selection of raw materials, wherein the raw materials for synthesizing the intermediate 2-3-5-M3 are as follows: 2-3-5-M2 and 2-1-2-M2;
(3) Synthesis of end product 2-3-5:
the synthesis of the final product 2-3-5 is based on the synthesis of the compound 2-1-2, except for the selection of the raw materials, the synthesis of 2-3-5 is as follows: a-7 and 2-3-5-M3.
The HPLC purity of the prepared compound 2-3-5 was 99.9%.
1H NMR (400 MHz, Chloroform-d) δ 8.86 (s, 1H), 8.65 (s, 1H), 7.90 (s, 1H), 7.71 ~7.63 (m, 2H), 7.58 ~7.50 (m, 8H), 7.36 (m, 7H).
Synthesis example 4: synthesis of Compound 2-4-4
(1) Synthesis of intermediates 2-4-4-M0, 2-4-4-M1, 2-4-4-M2:
the synthesis methods of the intermediates 2-4-4-M0, 2-4-4-M1 and 2-4-4-M2 refer to the synthesis of the intermediates 2-1-2-M0, and are different in the selection of raw materials, and the synthesis raw materials of the intermediates 2-4-4-M0, 2-4-4-M1 and 2-4-4-M2 are respectively as follows: a-8 and A-1, 2-4-4-M0 and A-2, A-0 and A-4;
(2) Synthesis of intermediate 2-4-4-M3:
the synthesis method of the intermediate 2-4-4-M3 refers to the synthesis of the intermediate 2-1-2-M4, and is different in the selection of raw materials, wherein the raw materials of the intermediate 2-4-4-M3 are 2-4-4-M1 and 2-4-4-M2;
(3) Synthesis of end product 2-4-4:
the synthesis method of the final product 2-4-4 refers to the synthesis of the compound 2-1-2, and is different in the selection of raw materials, and the synthesis raw materials of the final product 2-4-4 are A-9 and 2-4-4-M3.
The HPLC purity of the prepared compound 2-4-4 was 99.9%.
1H NMR (400 MHz, Chloroform-d) δ 8.09 (s, 1H), 7.90 (d, J = 6.4 Hz, 2H), 7.76 ~7.71 (m, 4H), 7.52 (m, 4H), 7.45 (m, 4H), 7.32 (m, 9H), 1.34 (m, 7H).
Synthesis example 5: synthesis of Compound 2-5-6
(1) Synthesis of intermediates 2-5-6-M0, 2-5-6-M1, 2-5-6-M2:
the synthesis methods of the intermediates 2-5-6-M0, 2-5-6-M1 and 2-5-6-M2 refer to the synthesis of the intermediates 2-1-2-M0, and are different in the selection of raw materials, and the synthesis raw materials of the intermediates 2-5-6-M0, 2-5-6-M1 and 2-5-6-M2 are respectively as follows: a-10 and A-1, 2-5-6-M0 and A-2, A-11 and A-4;
(2) Synthesis of intermediate 2-5-6-M3:
the synthesis method of the intermediate 2-5-6-M3 refers to the synthesis of the intermediate 2-1-2-M4, and is different in that raw materials are selected, and the raw materials of the intermediate 2-5-6-M3 are 2-5-6-M1 and 2-5-6-M2;
(3) Synthesis of end product 2-5-6:
the synthesis method of the compound 2-5-6 refers to the synthesis of the compound 2-1-2, and is different in the selection of raw materials, wherein the raw materials of the compound 2-5-6 are A-9 and 2-5-6-M3.
The HPLC purity of the prepared compound 2-5-6 was 99.9%.
1 H NMR (400 MHz, Chloroform-d) δ 7.76 (s, 1H), 7.65 (m, 2H), 7.46 (d,J= 6.4 Hz, 2H), 7.33 (m, 10H), 3.56 (m, 4H), 3.22 (s, 1H), 2.15 (m, 2H), 1.96 (m, 2H).
Synthesis example 6: synthesis of Compound 2-6-3
(1) Synthesis of intermediates 2-6-3-M0, 2-6-3-M1:
the synthesis method of the intermediates 2-6-3-M0 and 2-6-3-M1 refers to the synthesis of the intermediates 2-1-2-M0, and is different in that raw materials are selected, and the raw materials of the intermediates 2-6-3-M0 and 2-6-3-M1 are respectively A-12 and A-1, and 2-6-3-M0 and A-2;
(2) Synthesis of intermediate 2-6-3-M2:
the synthesis method of the intermediate 2-6-3-M2 refers to the synthesis of the intermediate 2-1-2-M4, and is different in raw material selection, wherein the synthesis raw materials of the intermediate 2-6-3-M2 are 2-6-3-M1 and 2-4-4-M2;
(3) Synthesis of end product 2-6-3:
the synthesis method of the final product 2-6-3 refers to the synthesis of 2-1-2, and is different in the selection of raw materials, wherein the raw materials for synthesizing the compound 2-6-3 are A-7 and 2-6-3-M2;
the HPLC purity of the prepared compound 2-6-3 was 99.9%.
1H NMR (400 MHz, Chloroform-d) δ 8.09 (s, 1H), 7.90 (d, J = 6.4 Hz, 2H), 7.71 (m, 2H), 7.50 (m, 8H), 7.35 (m, 7H).
Other compounds of the present application can be synthesized by selecting appropriate raw materials according to the ideas of the above synthesis examples 1-6, and can also be synthesized by selecting any other appropriate methods and raw materials.
The following compounds in patent CN113260605a were chosen as comparative example 1 (D-1) and comparative example 2 (D-2):
。
the testing method comprises the following steps:
testing the luminous intensity efficiency and CIE color coordinates of the organic electroluminescent device by adopting a brightness-current density-voltage (BJV) test system;
the measuring instrument was a Version-1.0.1.4 spectroscopic ellipsometer of Radiation technology company, and the refractive index (n) of each of the compounds of examples and comparative examples was measured by EMA (Effective Medium Approximation, effective medium modeling method) method at different wavelengths, wherein the material thin films were formed by vapor deposition of the compounds of each of the synthesis examples or comparative examples on a glass substrate at a vapor deposition rate of 0.1nm/s and a vapor deposition film thickness of 80nm. The refractive index (n) of the compounds of the synthesis example and comparative example was measured at different wavelengths with a glass substrate size of 200mm by 200 mm. The measurement results are shown in table 1.
Refractive index data and blue light device test data for each compound of Table 1
As can be seen from Table 1, synthesis examples 1-6 had lower refractive indices than comparative examples 1-2, the color purity was close, and the luminous efficiency of Synthesis examples 1-6 was significantly higher than that of comparative examples 1-2. In combination, the synthesis example has better device performance than the comparative example.
The foregoing description of the preferred embodiments of the invention is not intended to limit the invention to the precise form disclosed, and any such modifications, equivalents, and alternatives falling within the spirit and scope of the invention are intended to be included within the scope of the invention.
Claims (1)
1. A compound selected from the following structural formulas:
。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311465792.5A CN117185990B (en) | 2023-11-07 | 2023-11-07 | Compound and organic electroluminescent device comprising same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311465792.5A CN117185990B (en) | 2023-11-07 | 2023-11-07 | Compound and organic electroluminescent device comprising same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN117185990A CN117185990A (en) | 2023-12-08 |
| CN117185990B true CN117185990B (en) | 2024-01-30 |
Family
ID=88992818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311465792.5A Active CN117185990B (en) | 2023-11-07 | 2023-11-07 | Compound and organic electroluminescent device comprising same |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117185990B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111943902A (en) * | 2020-08-21 | 2020-11-17 | 长春海谱润斯科技有限公司 | Triarylamine compound and organic light-emitting device thereof |
| CN116283725A (en) * | 2023-01-16 | 2023-06-23 | 烟台显华科技集团股份有限公司 | Aromatic amine substituted dibenzofive-membered ring compound and application thereof |
-
2023
- 2023-11-07 CN CN202311465792.5A patent/CN117185990B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111943902A (en) * | 2020-08-21 | 2020-11-17 | 长春海谱润斯科技有限公司 | Triarylamine compound and organic light-emitting device thereof |
| CN116283725A (en) * | 2023-01-16 | 2023-06-23 | 烟台显华科技集团股份有限公司 | Aromatic amine substituted dibenzofive-membered ring compound and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN117185990A (en) | 2023-12-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5812583B2 (en) | Triazine derivative, method for producing the same, and organic electroluminescent device comprising the same | |
| US10604697B2 (en) | Color conversion sheet, light source unit including the same, display, and lighting apparatus | |
| US10907094B2 (en) | Pyrromethene-boron complex, color conversion composition, color conversion film, light source unit, display, and illumination apparatus | |
| KR101579490B1 (en) | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof | |
| JP6939787B2 (en) | Color conversion sheet, light source unit including it, display and lighting equipment | |
| CN110945389B (en) | Color conversion composition, color conversion film, and device comprising same | |
| US20210261531A1 (en) | Nitrogen-heterocyclic compound, display panel and display apparatus | |
| TW201204808A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2019061796A1 (en) | Organic compound with triazine and quinoxaline as core and application thereof in oled | |
| KR20160041124A (en) | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof | |
| CN112300144B (en) | Organic compound based on carbazole as core and application of organic compound in OLED | |
| KR20140121991A (en) | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof | |
| TW202030192A (en) | Materials for organic electroluminescent devices | |
| CN109970680A (en) | A kind of orange light material with AIE performance and its application in light conversion film | |
| CN117185990B (en) | Compound and organic electroluminescent device comprising same | |
| KR20240045144A (en) | Composition containing para-biphenyl substituted bicarbazole compounds and organic electroluminescent device containing same | |
| US10961260B2 (en) | Nitrogenous compound and color conversion film comprising same | |
| JP2022513608A (en) | Organic electroluminescence material and its preparation method and organic electroluminescence device | |
| CN107721904B (en) | Pyrene derivative and preparation method and application thereof | |
| CN112300199B (en) | Organic compound based on carbazole derivative structure and application of organic compound to OLED | |
| JP2021162665A (en) | Pyrromethene boron complex, color conversion composition, color conversion film, and light source unit, display and lighting device that comprise the same | |
| CN107868037A (en) | A kind of organic compound containing fluorenes and its application | |
| US10361382B2 (en) | Platinum complexes for blue OLED application | |
| CN117209422A (en) | Fluorine-containing ortho-substituted triarylamine compound and organic electroluminescent device | |
| CN113149889A (en) | Compound and organic electroluminescent device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |