CN115806563A - B-N-containing organic electroluminescent material and application thereof in electroluminescent device - Google Patents
B-N-containing organic electroluminescent material and application thereof in electroluminescent device Download PDFInfo
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Abstract
The invention provides a B-N-containing organic electroluminescent material and application thereof in an electroluminescent device. The structure of the organic electroluminescent material containing B-N is shown in general formulas (I), (II) and (III). The material introduces an electron-N absorption structure unit on the basis of a B-N structure, can effectively strengthen the multiple resonance effect of the B-N structure, increases an N conjugate plane, and adjusts a light-emitting spectrum; and the aromatic group on the arylamine is fixed by the introduced electron-withdrawing group to form a large rigid pi plane structure, so that the intramolecular vibration can be effectively inhibited, the high-efficiency organic luminescent material with narrow half-wave width can be obtained, and the commercial requirement can be met.
Description
Technical Field
The invention relates to the field of luminescent materials, in particular to a B-N-containing organic electroluminescent material and application thereof in an electroluminescent device.
Background
Organic Light Emission Diodes (OLED) devices have been widely used in the display and lighting industry, especially in mobile phone displays, and the latest mobile phone products introduced by mobile phone manufacturers like Apple, sumsang, huashi and millet all use OLED screens, which is mainly attributed to the excellent characteristics of OLED, such as self-luminescence, wide viewing angle, high contrast, fast response speed and capability of preparing flexible devices.
The OLED device currently commercialized has a multi-layer sandwich structure including an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a cathode, and the like. The anode generates holes and enters the light emitting layer through the hole injection layer and the transport layer, while electrons move from the cathode to the light emitting layer through the electron injection layer and the transport layer, and the holes and the electrons recombine in the light emitting layer to generate excitons. These excitons transition from an excited state to a ground state, thereby emitting visible light. In order to realize color display, the OLED device uses the additive color principle, that is, the light emitting layer is further divided into a blue light emitting layer, a green light emitting layer and a red light emitting layer, and different light emitting layers use organic materials with different light emitting colors.
When the OLED device is applied to display, it is required to have a low driving voltage, a high luminous efficiency, and a long life, and therefore, in realizing the gradual increase of display performance, the organic material undergoes the development from a fluorescent material to a phosphorescent material to a thermally activated delayed fluorescent material (TADF). At present, green light and red light materials are phosphorescent materials, which can emit light by utilizing singlet excitons and also can emit light by utilizing triplet excitons, so that the internal quantum efficiency can reach 100 percent, but the phosphorescent materials contain heavy metals, and have the problems of high price, poor material stability and the like; the blue light material is a fluorescent material, and only singlet excitons can be adopted for emitting light, although the TTA (two triplet excitons are converted into one singlet exciton) principle is applied, the theoretical efficiency is only 40%, and the market demand is far lower. TADF materials utilize small singlet-triplet energy level differences (Δ EST), triplet excitons can be converted to singlet excitons by intersystem crossing, and thus can also achieve 100% internal quantum efficiency, whereas TADF materials have strong charge transfer Characteristics (CT), too broad a spectral half-wave width, and are not conducive to high color purity displays.
Disclosure of Invention
Aiming at the existing problems of the organic materials, the invention provides a B-N organic luminescent material and application thereof in an organic luminescent device. The material introduces an electron-N absorption structure unit on the basis of a B-N structure, can effectively strengthen multiple resonance effect of the B-N structure, enlarge the multiple resonance effect range, increase an N conjugate plane and adjust a luminescence spectrum; and the aromatic group on the arylamine is fixed by the introduced electron-withdrawing group to form a large rigid pi plane structure, so that the intramolecular vibration can be effectively inhibited, the high-efficiency organic luminescent material with narrow half-wave width can be obtained, and the commercial requirement can be met.
The invention also provides an organic electroluminescent material containing a B-N structure, which has a structural general formula shown in one of formulas (I), (II) and (III):
wherein:
X 1 to X 4 Are respectively and independently selected from electron-withdrawing units
Ar 1 To Ar 10 Each independently selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 30 carbon atoms, or Ar 1 And Ar 2 、Ar 3 And Ar 4 、Ar 4 And Ar 5 、Ar 5 And Ar 7 Independently form a single bond,-any one of-C-, -C = N-, -C = P-, -C ≡ C-is linked to a ring; the hetero atom of the heteroaryl is one or more of N, S, O, P, B and Si;
ar is 1 To Ar 10 Wherein the substituent (b) is independently one or more substituents selected from the group consisting of hydrogen, deuterium, a cyano group, a nitro group, a halogen group, a hydroxyl group, an alkylthio group having 1 to 4 carbon atoms, an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, a heteroarylamino group having 2 to 24 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 60 carbon atoms, and a heteroarylalkyl group having 6 to 30 carbon atoms.
The aryl is selected from one or more of phenyl, naphthyl, anthryl, binaphthyl, phenanthryl, dihydrophenanthryl, \33534yl, perylenyl, tetracene, pentacene, benzoperylene, benzocyclopentadienyl, spirofluorenyl and fluorenyl.
Preferably, the following components: the aryl is selected from one or more of phenyl, naphthyl, anthryl, phenanthryl, dihydrophenanthryl, tetracene, pentacene, benzoperylene, benzocyclopentadienyl, spirofluorenyl and fluorenyl.
The heteroaryl group is selected from one or more of pyrrolyl, imidazolyl, thienyl, furyl, 1, 2-thiazolyl, 1, 3-thiazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, thiadiazolyl, selenadiazolyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, pyridyl, pyrazinyl, pyrimidinyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, indole, isoindole, benzimidazole, naphthoimidazole, phenanthroimidazole, benzotriazole, purine, benzoxazole, naphthoxazole, phenanthrooxazole, benzothiadiazolyl, benzoselenadiazolyl, benzotriazolyl, quinolyl, isoquinolyl, benzopyrazinyl, benzothiophenyl, benzofuranyl, benzopyrazolyl, carbazolyl, acridinyl, dibenzofuranyl, silafluorenyl, dibenzothiophenyl-5, 5-dioxy, naphthothiadiazolyl, naphthoselenadiazolyl and 10, 15-dihydro-5H-indol [3, 2'-c ] 3,2, 3' -c; most preferably, the heteroaryl group is one or more selected from the group consisting of pyrrolyl, imidazolyl, thienyl, furyl, 1, 2-thiazolyl, 1, 3-thiazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, thiadiazolyl, selenadiazolyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, pyridyl, pyrazinyl, pyrimidinyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, indole, isoindole, benzimidazole, naphthoimidazole, phenanthroimidazole, benzotriazole, purine, benzoxazole, naphthoxazole, phenanthrooxazole, benzothiadiazolyl, benzotriazolyl, quinolinyl, isoquinolinyl, benzoxazinyl, benzothienyl, benzofuranyl, benzopyrolyl, carbazolyl, acridinyl, dibenzothienyl, dibenzofuranyl, dibenzothiophene-5, 5-dioxy, naphthothiadiazolyl, naphthoselenadiazolyl and 10, 15-dihydro-5H-diindolyl [3,2 '-a ] 2, 3' -c ].
Preferably, the general structural formula is shown in one of formulas (a) to (i),
in structural formulae (a) to (i), ar 1 -Ar 10 Are as defined in structural formulae (I) to (III).
More preferably: ar in structural formulae (a) to (i) 1 、Ar 2 、Ar 4 、Ar 6 、Ar 8 、Ar 10 Independently selected from one of the formulae Ar-1 to Ar-28, ar 3 、Ar 5 Independently selected from one of the formulae Ar-29 to Ar-65, ar 7 Selected from one of the formulae Ar-66 to Ar-93, ar 9 Selected from one of the formulae Ar-94 to Ar-99.
Wherein, P 1 Denotes the site of attachment to the boron atom, P 2 、P 3 、P 4 、P 5 Respectively represent with X 1 、X 2 、X 3 、X 4 The dotted line is the bond to which it is attached;
R 1 each independently selected from a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a fluorine atom, a cyano group, a phosphoric acid or a salt thereof, a linear or branched C1-20 alkyl group, a linear or branched C1-20 alkyl-substituted silane group, a C6-30 substituted or unsubstituted aryl group, a C5-30 substituted or unsubstituted heteroaryl group, or R 1 A single bond, -C-C-, -C = N-, -C = P-, -C ≡ C-, and,
Any one of which is bonded to form a ring; the hetero atom in the heteroaryl is selected from one or more of N, O or S, and the substitution in the aryl or the heteroaryl is substituted by halogen element or C1-C4 alkyl.
Preferably: r is 1 Each independently selected from hydrogen atom, protium atom, deuterium atom, tritium atom, fluorine atom, cyano group, linear or branched C1-8 alkyl group, C6-10 substituted or unsubstituted aryl group, C5-10 substituted or unsubstituted heteroaryl group, or R 1 Are linked with each other by any one of single bond and-C-C-to form a ring; the hetero atom in the heteroaryl is selected from one or more of N, O or S, and the aryl or the heteroaryl is substituted by C1-C4 alkyl.
Further preferably, R 1 Each independently selected from a hydrogen atom, a linear or branched C1-4 alkyl group, a phenyl group, or R 1 To each other withAny one of a single bond and-C-C-is bonded to form a ring.
The general formula of the structure is shown as formula (a) or (d), wherein Ar 1 、Ar 2 As shown in one of Ar-1 to Ar-16, ar-19 to Ar-26, ar 4 Is shown as one of Ar-1, ar-4, ar-6, ar-8, ar-10, ar-11, ar-16 and Ar-25, ar 3 、Ar 5 Such as Ar-29, ar-32, ar-34, ar-36, ar-37, ar-38, ar-54, ar-59, ar-64.
The structure is shown in the following formula, but is not limited to the listed structural formula:
the second invention of the invention provides an organic electroluminescent device, which comprises at least one layer of organic electroluminescent material with a functional layer containing B-N condensed rings;
preferably, the B-N condensed ring organic electroluminescent material is used as a luminescent layer material;
more preferably, the B-N condensed ring organic electroluminescent material is used as a doping material or a sensitizer material of the light-emitting layer;
the invention provides a B-N organic luminescent material and application thereof in an organic luminescent device. The material introduces an electron-N absorption structure unit on the basis of a B-N structure, can effectively strengthen multiple resonance effect of the B-N structure, enlarge the multiple resonance effect range, increase an N conjugate plane and adjust a luminescence spectrum; and the aromatic group on the arylamine is fixed by the introduced electron-withdrawing group to form a large rigid n-shaped plane structure, so that intramolecular vibration can be effectively inhibited, and the high-efficiency organic luminescent material with narrow half-wave width can be obtained, thereby meeting the commercial requirement.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent bottom-emitting device according to the present invention.
Detailed Description
The present invention does not require a method for synthesizing the material, and the following examples are given for describing the present invention in more detail, but are not limited thereto. The starting materials used in the following syntheses are all commercial products unless otherwise specified.
Example 1:
synthesis of compound structure 1:
synthesis of compound 1 c:
a100 ml three-necked flask was charged with (1 b) (845mg, 2.56mmol), (1 a) (1.0g, 5.12mmol), cuI (346mg, 1.82mmol), potassium carbonate (2.12g, 15.4mmol) and DMF (40 ml), and the reaction was stirred at 180 ℃ for 22 hours under nitrogen. After the reaction is finished, adding 100mL of water under stirring to separate out a product, after suction filtration, dissolving by using 10mL of DCM, adding 100mL of n-hexane to separate out, and obtaining a yellow crude product by suction filtration. Silica gel column chromatography gave 0.6g of yellow solid powder in 50.4% yield. Hydrogen spectrum dataThe following were used: 1 H NMR(400MHz,CDCl 3 )δ8.21(d,4H),8.15(d,1H),7.70(t,4H), 7.52(d,6H),7.23(t,5H).
synthesis of Compound 1:
1c (300mg, 0.6 mmol) and o-CB (30 ml) were charged in a three-necked flask, nitrogen was purged three times, and BI was weighed in a fume hood 3 (0.99g, 2.4 mmol) was quickly added to the flask, stirred for 0.5h, and then warmed to 200 ℃ for reaction for 48h. After the reaction is finished, cooling and filtering are carried out, a filter cake is subjected to ultrasonic treatment by DCM and normal hexane, and yellow powder 30mg and the yield is 11% are obtained through filtering. The hydrogen spectra data are as follows: 1 H NMR(400MHz,CDCl 3 )δ8.06(dd,J＝7.7,1.6Hz,2H),8.01(dd,J＝7.3,1.1Hz, 2H),7.77(dd,J＝7.5,1.1Hz,2H),7.56(ddd,J＝8.1,7.2,1.6Hz,2H),7.38(ddd,J＝8.6,7.2,1.5 Hz,2H),7.34–7.25(m,5H),6.91–6.85(m,2H).
example 2:
synthesis of compound structure 2:
the same synthesis as compound structure 1 was performed except that the starting material 1a was changed to 2a, and the compound 2 was yellow powder, with a yield of 8%. 1 H NMR(400MHz,CDCl 3 )δ8.00(d,J＝2.0Hz,2H),7.89(d,J＝2.2Hz,2H),7.63(d,J ＝2.2Hz,2H),7.41(dd,J＝6.9,2.1Hz,2H),7.34–7.27(m,3H),6.91–6.85(m,2H),1.34(d,J＝ 4.8Hz,36H).
Example 3:
synthesis of compound structure 8:
synthesis of compound 8 c:
a100 ml three-necked flask was charged with (8 b) (0.85g, 3.0 mmol), (1 a) (0.6mg, 3.1mmol), cuI (0.23g, 1.2mmol), potassium carbonate (1.24g, 9.0 mmol) and DMF (50 ml), and the reaction was stirred at 150 ℃ for 12 hours under nitrogen. After the reaction is finished, 100ml of water is added under stirring to separate out a product,after suction filtration and drying, the filter cake was dissolved in dichloromethane and subjected to silica gel column chromatography to obtain 0.77g of a yellow solid with a yield of 74%. The hydrogen spectra data are as follows: 1 H NMR(400MHz, CDCl 3 )δ8.05(dd,J＝7.7,1.6Hz,2H),7.52(ddd,J＝8.0,7.3,1.8Hz,2H),7.37(dd,J＝7.2,1.4 Hz,1H),7.35–7.24(m,6H),7.11(ddd,J＝7.0,2.3,1.4Hz,1H).
synthesis of compound 8 e:
a100 ml three-necked flask was charged with (8 c) (0.7g, 2.0mmol), (8 d) (0.61mg, 2.21mmol), cuI (0.23g, 1.2mmol), potassium carbonate (1.24g, 9.0mmol), and DMF (50 ml), and the mixture was stirred at 180 ℃ for 12 hours under nitrogen. After the reaction, 100ml of water was added with stirring to precipitate the product, which was then filtered off and dried, the filter cake was dissolved in dichloromethane and subjected to silica gel column chromatography to obtain 0.91g of a yellow solid with a yield of 83%. The hydrogen spectra data are as follows: 1 H NMR(400MHz, CDCl 3 ) δ 8.07 (ddd, J =12.9,7.7,1.7hz, 3h), 7.68-7.59 (m, 2H), 7.57-7.48 (m, 3H), 7.42 (qd, J =4.1,3.6,1.7hz, 3h), 7.39-7.25 (m, 8H), 7.02 (dt, J =7.3,1.4hz, 2h), 6.34 (t, J =1.9hz, 1h) synthesis of compound 8:
same as the synthesis of compound 1, yield 12%. The hydrogen spectra data are as follows: 1 H NMR(400MHz,CDCl 3 )δ8.10(dd, J＝7.7,1.9Hz,1H),8.06(dd,J＝7.7,1.5Hz,1H),8.01(dd,J＝7.3,1.1Hz,1H),7.66(dd,J＝7.5, 1.1Hz,1H),7.64–7.53(m,4H),7.44–7.38(m,5H),7.35–7.23(m,4H),6.88(ddd,J＝7.1,5.9, 1.1Hz,2H).
example 4:
synthesis of compound structure 121:
synthesis of compound 121 c:
as with the synthesis of compound 1c, the different charge changes were 121a for 1a and 8b for 1b, with 68% yield of 121c. The hydrogen spectra data are as follows: 1 H NMR(400MHz,CDCl 3 )δ7.40–7.34(m,7H),7.32(dd,J＝6.8,1.5 Hz,5H),7.29(dd,J＝7.2,1.4Hz,1H),7.23–7.14(m,4H),7.01(dd,J＝7.3,2.0Hz,2H),6.34(t,J ＝2.1Hz,1H).
synthesis of compound 121 d:
121c (0.95g, 2mmol) and 20mL of acetic acid were added to a three-necked flask, heated to 100 ℃ and 5mL of H was slowly added from above the reflux condenser 2 O 2 And reacting for 2 hours. Cooled to room temperature, filtered directly, the filter cake slurried with DCM, filtered again to give 0.87g of white powder in 81% yield. The hydrogen spectrum data are as follows: 1 H NMR(400MHz,DMSO-d 6 )δ8.38–7.87(m,8H), 7.64(s,4H),7.41(s,4H),6.83(s,4H).
synthesis of compound 121:
same as the synthesis of compound 1, yield 7%. The hydrogen spectra data are as follows: 1 H NMR(400MHz,DMSO-d 6 )δ7.92 (ddd,J＝8.5,3.8,1.3Hz,4H),7.68(dd,J＝7.3,1.1Hz,2H),7.57–7.48(m,4H),7.44(ddd,J＝ 7.7,7.0,1.5Hz,2H),7.34–7.23(m,3H),6.91–6.85(m,2H).
example 5:
synthesis of compound structure 124:
synthesis of compound 124 a:
as with the synthesis of compound 121c, the charge was varied from 2eq to 1.2eq at 121 a. The yield of 124a was 87%. The hydrogen spectra data are as follows: 1 H NMR(400MHz,CDCl 3 ) δ 7.39-7.35 (m, 3H), 7.32 (m, 5H), 7.28 (m, 1H), 7.21-7.15 (m, 2H), 7.10 (m, 1H.) synthesis of compound 124 b:
the same synthesis as for compound 124a except that 121a was changed to 124a and 121b was changed to 124b was carried out in 73% yield. The hydrogen spectrum data are as follows: 1 H NMR(400MHz,CDCl 3 )δ7.99(d,J＝1.8Hz,1H),7.86(m,2H),7.79 (d,J＝1.9Hz,1H),7.55–7.48(m,2H),7.39–7.27(m,12H),7.22–7.14(m,3H),6.34(t,J＝2.1 Hz,1H).
synthesis of compound 124:
the same as the synthesis of compound 121, except that 121c was changed to 124c, yield10 percent. The hydrogen spectra data are as follows: 1 H NMR(400MHz,DMSO-d 6 )δ8.36(d,J＝1.8Hz,1H),7.98(dd,J＝7.3,1.1Hz,1H),7.92(m, 3H),7.83(dt,J＝7.3,1.6Hz,1H),7.69(dd,J＝7.3,1.1Hz,1H),7.58–7.48(m,4H),7.48–7.41 (m,4H),7.36(td,J＝7.2,1.3Hz,1H),7.33–7.21(m,2H),6.91–6.84(m,2H).
example 6:
synthesis of compound structure 134:
the synthesis was identical to compound 124 except that 124b was changed to 134a,134 yield was 7%. The hydrogen spectrum data are as follows: 1 H NMR(400MHz,DMSO-d 6 )δ8.03–7.88(m,3H),7.83(dd,J＝7.3,1.1Hz,1H),7.79–7.71 (m,2H),7.63–7.50(m,5H),7.50–7.40(m,4H),7.36–7.23(m,2H),6.88(m,2H).
it will be appreciated by those skilled in the art that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other structures of the compounds of the present invention.
Example 7:
the B-N organic electroluminescent material is used for preparing an organic electroluminescent bottom-emitting device, and the structure of the device is shown in figure 1. Firstly, a transparent conductive ITO glass substrate 10 (with an anode 20 on the upper surface) is washed by deionized water, ethanol, acetone and deionized water in sequence, dried at 80 ℃, and then treated by oxygen plasma for 30min. Then, the vacuum is applied to a deposition machine<4*10 -4 HATCN with the thickness of 10nm is respectively evaporated under pa to form a hole injection layer 30; evaporating a compound HTL to form a hole transport layer 40 with a thickness of 40 nm; an EBL (electron blocking layer) 50 with a thickness of 10nm is vapor-deposited on the hole transport layer; then, an EML (host material (host 1: host2= 1): guest material = 94%, light-emitting layer) 60 with a thickness of 40nm was evaporated, and the light-emitting layer was composed of a B — N organic electroluminescent material (structure 1, 6%) doped with the host material; an ETL (electron transport layer) 70 with a thickness of 40nm was evaporated on the light emitting layer, and the electron transport layer was composed of two materials, ETL1 and LiQ. Evaporating 1nm metal ytterbium as an electron injection layer80 and 100nm Ag as device cathode 90.
Example 8-example 12 and comparative example 1:
examples 8-examples 12 and comparative example 1 organic electroluminescent devices were fabricated in the same manner as in example 7, except that the guest materials in the light-emitting layer were structure 2, structure 8, structure 121, structure 122, structure 134 and comparative example 1 in the present invention, respectively.
Example 13:
the organic electroluminescent device of example 13 was fabricated in the same manner as in example 7, except that the material of the light emitting layer was composed of host 3 and comparative example 2, respectively (host 3: comparative example 2=97%: 3%), and the thickness was 20nm.
The chemical structures of the materials of comparative example 1 and comparative example 2 are as follows:
the electrical and optical properties of the electroluminescent devices of examples 7 to 12 and comparative examples 1 and 2 were measured at 0.4mA as in table 1.
TABLE 1
As can be seen from the data in table 1, under the same conditions, the B-N organic electroluminescent material of the present invention applied to an organic electroluminescent device has a narrow half-wave width, i.e., it has a higher color purity in a top emission device (compared to comparative example 1) to achieve a more excellent display effect; compared with comparative example 2, the device luminescence wavelength of the B-N organic electroluminescent material of the invention is obviously red-shifted and is positioned in a green light region (> 500 nm), and the luminescence color can be adjusted, which is different from the conventional B-N organic electroluminescent material (comparative example 2, luminescence wavelength: 459 nm).
Claims (15)
1. The structure of the organic electroluminescent material containing the B-N structure is shown as one of general formulas (I), (II) and (III):
wherein:
X 1 to X 4 Are respectively and independently selected from electron-withdrawing units
Ar 1 To Ar 10 Each independently selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 30 carbon atoms, or Ar 1 And Ar 2 、Ar 3 And Ar 4 、Ar 4 And Ar 5 、Ar 5 And Ar 7 Independently linked into a ring by any one of single bond, -C-C-, -C = N-, -C = P-, -C ≡ C-; the hetero atom of the heteroaryl is one or more of N, S, O, P, B and Si;
ar is 1 To Ar 10 Wherein the substitution is independently by hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxyl group, alkylthio group having 1 to 4 carbon atoms, alkyl group having 1 to 30 carbon atoms, cycloalkyl group having 1 to 20 carbon atoms, aryloxy group having 6 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, alkylamino group having 1 to 30 carbon atoms, arylamino group having 6 to 30 carbon atoms, aralkylamino group having 6 to 30 carbon atoms, heteroarylamino group having 2 to 24 carbon atoms, alkylsilyl group having 1 to 30 carbon atoms, arylsilyl group having 6 to 30 carbon atoms, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, or arylsilyl group having 2 to 24 carbon atomsAn alkynyl group, an aralkyl group having 7 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 60 carbon atoms or a heteroarylalkyl group having 6 to 30 carbon atoms.
2. The organic electroluminescent material according to claim 1, wherein the aryl group is selected from one or more of phenyl, naphthyl, anthryl, binaphthyl, phenanthryl, dihydrophenanthryl, 33534yl, peryleneyl, tetracene, pentacene, benzoperylene, benzocyclopentadienyl, spirofluorenyl, and fluorenyl.
3. The organic electroluminescent material according to claim 2, wherein the aryl group is selected from one or more of phenyl, naphthyl, anthryl, phenanthryl, dihydrophenanthryl, tetracene, pentacene, benzoperylene, benzocyclopentadienyl, spirofluorenyl and fluorenyl.
4. The organic electroluminescent material according to claim 1, wherein the heteroaryl group is selected from one or more of pyrrolyl, imidazolyl, thienyl, furyl, 1, 2-thiazolyl, 1, 3-thiazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, thiadiazolyl, selenadiazolyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, pyridyl, pyrazinyl, pyrimidinyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, indole, isoindole, benzimidazole, naphthoimidazole, phenanthroimidazole, benzotriazole, purine, benzoxazole, naphthoxazole, phenanthrooxazole, benzothiadiazolyl, benzoselenadiazolyl, benzotriazolyl, quinolyl, isoquinolyl, benzopyrazinyl, benzothiophenyl, benzofuranyl, benzopyrazolyl, carbazolyl, acridinyl, dibenzothienyl, dibenzofuranyl, silafluorenyl, dibenzothiophene-5, 5-dioxy, naphthothiadiazolyl, naphthoselenadiazolyl, and [ 2, 10,15, 3-dihydro-carbazolyl ] indole; most preferably, the heteroaryl group is one or more selected from the group consisting of pyrrolyl, imidazolyl, thienyl, furyl, 1, 2-thiazolyl, 1, 3-thiazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, thiadiazolyl, selenadiazolyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, pyridyl, pyrazinyl, pyrimidinyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, indole, isoindole, benzimidazole, naphthoimidazole, phenanthroimidazole, benzotriazole, purine, benzoxazole, naphthoxazole, phenanthrooxazole, benzothiadiazolyl, benzotriazolyl, quinolyl, isoquinolyl, benzopyrazinyl, benzothiophenyl, benzofuranyl, benzopyrolyl, carbazolyl, acridinyl, dibenzothienyl, dibenzothiophene-5, 5-dioxy, naphthothiadiazolyl, naphthoselenadiazolyl, and 10, 15-dihydro-5H-diindolyl [3, 2' -c ] carbazolyl.
5. The organic electroluminescent material according to any one of claims 1 to 4, which has a general structural formula shown in one of the formulae (a) to (i),
in structural formulae (a) to (i), ar is 1 -Ar 10 Are as defined in structural formulae (I) to (III).
6. The organic electroluminescent material according to claim 5, wherein Ar in structural formulas (a) to (i) 1 、Ar 2 、Ar 4 、Ar 6 、Ar 8 、Ar 10 Independently selected from one of the formulae Ar-1 to Ar-28, ar 3 、Ar 5 Independently selected from one of the formulae Ar-29 to Ar-65, ar 7 Selected from one of the formulae Ar-66 to Ar-93, ar 9 Selected from one of the formulae Ar-94 to Ar-99,
wherein, P 1 Denotes the site of attachment to the boron atom, P 2 、P 3 、P 4 、P 5 Respectively represent with X 1 、X 2 、X 3 、X 4 The dotted line is the bond of the corresponding linkage;
R 1 each independently selected from a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a fluorine atom, a cyano group, a phosphoric acid or a salt thereof, a linear or branched C1-20 alkyl group, a linear or branched C1-20 alkyl-substituted silane group, a C6-30 substituted or unsubstituted aryl group, a C5-30 substituted or unsubstituted heteroaryl group, or R 1 A single bond, -C-C-, -C = N-, -C = P-, -C ≡ C-, and,
Any one of which is bonded to form a ring; the hetero atom in the heteroaryl is selected from one or more of N, O or S, and the substitution in the aryl or the heteroaryl is substituted by halogen elements or C1-C4 alkyl.
7. The organic electroluminescent material according to claim 6, wherein R 1 Each independently selected from hydrogen atom, protium atom, deuterium atom, tritium atom, fluorine atom, cyano group, linear or branched C1-8 alkyl group, C6-10 substituted or unsubstituted aryl group, C5-10 substituted or unsubstituted heteroaryl group, or R 1 Are linked with each other by any one of single bond and-C-C-to form a ring; the hetero atom in the heteroaryl is selected from one or more of N, O or S, and the substitution in the aryl or the heteroaryl is the substitution of C1-C4 alkyl.
8. The organic electroluminescent material according to claim 7, wherein R is 1 Each independently selected from a hydrogen atom, a linear or branched C1-4 alkyl group, a phenyl group, or R 1 Are mutually bound by a single bond, -C-C-It means a key joint to form a ring.
9. The organic electroluminescent material according to claim 8, which has a general structural formula of formula (a) or (d), wherein Ar is 1 、Ar 2 As shown in one of Ar-1 to Ar-16, ar-19 to Ar-26, ar 4 Is shown as one of Ar-1, ar-4, ar-6, ar-8, ar-10, ar-11, ar-16 and Ar-25, ar 3 、Ar 5 Such as Ar-29, ar-32, ar-34, ar-36, ar-37, ar-38, ar-54, ar-59, ar-64.
10. The organic electroluminescent material according to claim 1, which has a structure represented by one of the following formulae:
11. use of an organic electroluminescent material according to any one of claims 1 to 10 in an electroluminescent device.
12. Use according to claim 11, wherein the electroluminescent device comprises at least one functional layer comprising an organic electroluminescent material as claimed in any one of claims 1 to 10.
13. Use according to claim 12 of an organic electroluminescent material according to any one of claims 1 to 10 as a material for a light-emitting layer.
14. Use according to claim 13 of an organic electroluminescent material according to any of claims 1 to 10 as a doping material or sensitizer material for the light-emitting layer.
15. An illumination or display element, characterized in that: an electroluminescent device prepared comprising the organic electroluminescent material as claimed in any one of claims 1 to 10.
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| PCT/CN2022/110124 WO2023035820A1 (en) | 2021-09-13 | 2022-08-04 | B-n-containing organic electroluminescent material and use thereof in electroluminescent device |
| TW111130487A TW202311496A (en) | 2021-09-13 | 2022-08-12 | A kind of organic electroluminescent material containing b-n and its application in electroluminescent device |
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| CN202111067045 | 2021-09-13 | ||
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117003784A (en) * | 2023-10-07 | 2023-11-07 | 吉林大学 | Boron-nitrogen-containing polycyclic aromatic hydrocarbon based on five-membered heterocyclic structure, preparation method and organic electroluminescent device |
| CN117209451A (en) * | 2023-09-15 | 2023-12-12 | 石家庄市田航科技有限公司 | Blue fluorescent material and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20220084200A (en) * | 2016-04-26 | 2022-06-21 | 가꼬우 호징 관세이 가쿠잉 | Organic Electroluminescence Device |
| WO2019235402A1 (en) * | 2018-06-04 | 2019-12-12 | 学校法人関西学院 | Polycyclic aromatic compounds and polymers of same |
| KR20190127529A (en) * | 2018-12-19 | 2019-11-13 | 머티어리얼사이언스 주식회사 | Organic electroluminescent device |
| CN110407859B (en) * | 2019-07-18 | 2022-09-20 | 清华大学 | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material |
| CN110790782A (en) * | 2019-11-11 | 2020-02-14 | 北京大学深圳研究生院 | Dark blue organic luminescent material and preparation method and application thereof |
| CN112898324A (en) * | 2019-12-03 | 2021-06-04 | 北京鼎材科技有限公司 | Compound, application thereof and organic electroluminescent device |
| CN113929709A (en) * | 2020-06-29 | 2022-01-14 | 江苏三月科技股份有限公司 | Boron-nitrogen-containing organic compound and organic electroluminescent device comprising same |
| WO2022018181A1 (en) * | 2020-07-24 | 2022-01-27 | Cynora Gmbh | Organic molecules for optoelectronic devices |
| CN112480154B (en) * | 2020-11-26 | 2023-01-24 | 深圳大学 | Chiral thermal activation delayed fluorescent material and circular polarization electroluminescent device thereof |
| CN114773366B (en) * | 2022-03-22 | 2023-11-28 | 苏州大学 | Carbonyl condensed boron nitrogen derivative and preparation method and application thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117209451A (en) * | 2023-09-15 | 2023-12-12 | 石家庄市田航科技有限公司 | Blue fluorescent material and preparation method and application thereof |
| CN117003784A (en) * | 2023-10-07 | 2023-11-07 | 吉林大学 | Boron-nitrogen-containing polycyclic aromatic hydrocarbon based on five-membered heterocyclic structure, preparation method and organic electroluminescent device |
| CN117003784B (en) * | 2023-10-07 | 2024-01-05 | 吉林大学 | Boron-nitrogen-containing polycyclic aromatic hydrocarbon based on five-membered heterocyclic structure, preparation method and organic electroluminescent device |
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