Indole carbazoloquinoline compound and application thereof

Abstract

The invention relates to the technical field of organic electroluminescent materials, in particular to an indolocarbazoloquinoline compound and application thereof, and the structure of the indolocarbazoloquinoline compound is as follows: # imgabs0 #; r represents substituted or unsubstituted C6-C20 aryl or heterocyclic aryl, and the substituent is selected from at least one of deuterium, phenyl and alkyl; heteroatoms in the heterocyclic aryl are selected from at least one of O, N and S. The parent structure of the indolocarbazoloquinoline compound is a six-membered ring rigid fused ring structure, the indolocarbazoloquinoline compound contains quinoline and indolocarbazole heterocyclic base structures, has a strong electron donating and withdrawing effect between molecules and has relatively large steric hindrance, and a pi-pi conjugation effect between six-membered rings formed by the indolocarbazole and quinoline structures of the indolocarbazoloquinoline compound has relatively large steric hindrance. Therefore, electrons can be better transited from a ground state to an excited state, and more efficient energy is released when the electrons return to the ground state. And the applied organic electroluminescent device is high in luminous efficiency and long in service life.

Description

Technical Field

[0001] The invention relates to an indolecarbazole-quinoline compound and application thereof, belonging to the technical field of organic electroluminescent materials. Background Art

[0002] As the third generation of display materials, OLED is gaining increasing status in the display field. More and more industries are gradually increasing their demand for OLED display materials. As the three basic luminescent materials of OLED: red light materials, green light materials, and blue light materials, with the continuous progress of the chemical industry and manufacturing industry, the types of OLED materials are becoming more diversified.

[0003] Green light materials are one of the key components of OLED materials. The high efficiency, fast response and low cost of existing green light materials have become the requirements of market applications, and the development of good green light materials has become an important breakthrough. Excellent green light materials have strong anti-interference ability due to their short wavelength and high frequency, which enables electrons to efficiently transition from the ground state to the excited state, and display high-definition green light at low voltage.

[0004] With the continuous development of the display field, high definition can no longer meet people's needs. With the emergence of ultra-high definition and 4K images, the demand for high-quality green light is even stronger, and the level and fineness of color need to be better transitioned. Good color purity has become a key breakthrough for green light materials. Unlike red and blue light materials, green light materials are affected by broadening or shoulder peaks, which causes large fluctuations in their CIE coordinates and large changes in color purity. Their own luminous efficiency and service life are greatly reduced, and high-efficiency green light has become a broader market prospect.

[0005] The continuous innovation and development of green light materials have enabled OLED technology to flourish in multiple fields such as wearables and vehicles. High-efficiency green light requires more mature technology and better costs to meet market demand. It has injected more vitality into the display field and, with the strong support of the country, has provided a more solid guarantee for the display field. To develop high-efficiency green light materials has become the development direction of the new OLED material field. Summary of the invention

[0006] In view of the deficiencies in the prior art, the present invention provides an indolecarbazole-quinoline compound and an application thereof. The indolecarbazole-quinoline compound is applied to an OLED device, has good green light primary color purity, and can significantly improve the luminous efficiency and service life of the device.

[0007] The technical solution of the present invention to solve the above technical problems is as follows: an indolecarbazole-quinoline compound, the structure of the indolecarbazole-quinoline compound is shown in the following general formula [I]: General formula [I]; In the general formula [I], R represents a substituted or unsubstituted C6-C20 aryl or heterocyclic aryl group, wherein the substituent is selected from at least one of deuterium, phenyl, and alkyl; and the heteroatom in the heterocyclic aryl group is selected from at least one of O, N, and S.

[0008] Further, R is selected from substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, pyrenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, carbazolyl, fluorenyl; The substituent is selected from at least one of deuterium, phenyl, and C1-C3 alkyl.

[0009] Furthermore, the R is selected from any one of the following group structures: .

[0010] Furthermore, the indolecarbazole-quinoline compound is selected from any one of the following structures:

[0011] The invention also discloses an organic electroluminescent device, in which the indolecarbazole and quinoline compounds are applied.

[0012] Furthermore, the organic layer of the organic electroluminescent device includes at least one of the indolecarbazole and quinoline compounds.

[0013] Furthermore, the organic layer of the organic electroluminescent device includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

[0014] Furthermore, the indolecarbazole-quinoline compound is applied to the light-emitting layer of an organic electroluminescent device.

[0015] Furthermore, the indolecarbazole-quinoline compound is used as a main material of a light-emitting layer of an organic electroluminescent device.

[0016] Furthermore, the indolecarbazole-quinoline compound is used as a luminescent material in OLED lighting and OLED display panels, and the luminescent material is used alone or after doping to include one or more of red luminescent materials, green luminescent materials and blue luminescent materials.

[0017] The invention also discloses an electronic device, characterized in that the electronic device comprises the organic electroluminescent device of the invention.

[0018] The beneficial effects of the present invention are: The parent structure of the indolecarbazole and quinoline compound of the present invention is a six-membered rigid condensed ring structure formed by indolecarbazole and quinoline, which contains quinoline and indolecarbazole heterocyclic basic structures, has a strong electron-donating and electron-withdrawing effect between molecules, has a large steric hindrance, and the π-π conjugated effect between the six-membered rings formed by the indolecarbazole and quinoline structures enables electrons to better transition from the ground state to the excited state, and release more efficient energy when returning to the ground state. The final device achieves efficient green light emission, which significantly improves the luminous efficiency and life of the device.

[0019] The OLED organic light-emitting device prepared from the indolecarbazole and quinoline compounds provided by the present invention has significantly improved luminous efficiency and working life characteristics and good stability.

[0020] The organic light-emitting device made by using the indolecarbazole and quinoline compounds provided by the present invention can be applied to the highly practical OLED industry, surface-emitting OLED luminous bodies for lighting, flexible luminous bodies, etc., and has a good application prospect. DETAILED DESCRIPTION

[0021] The specific implementation of the present invention is described in detail below. The present invention can be implemented in many other ways than those described herein, and those skilled in the art can make similar improvements without violating the connotation of the present invention, so the present invention is not limited by the specific embodiments disclosed.

[0022] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art to which the present invention belongs. The terms used are only for describing specific embodiments and are not intended to limit the present invention.

[0023] 1. Preparation Example Synthesis of the matrix: 1. Synthesis of Compound A: ; Add 100mmol of compound 3-bromo-2-chloroaniline and 100g of acetonitrile to the reaction bottle, start stirring, protect with nitrogen, heat to 20-30℃, start temperature-controlled dripping of 600mmol hydrochloric acid, after the dripping is completed, keep warm for 1h, cool to 0-10℃, and temperature-controlled dripping of 150mmol sodium nitrite aqueous solution (150mmol sodium nitrite is prepared into a 30% aqueous solution). After the dripping is completed and kept warm for 1h, the prepared reaction solution is temperature-controlled at 0-10℃ and dripped into the hydrochloric acid solution of tin chloride (200mmol tin chloride and 500mmol hydrochloric acid are prepared into a solution), after the dripping is completed and kept warm for 1h, heat to 20-30℃ and keep warm for 3h. After post-treatment, filter the reaction solution, and beat the filter cake with toluene to obtain 20.6g of compound A, with a yield of 80%. Mass spectrum: 257.9.

[0024] Hydrogen spectrum: 1 H NMR (500 MHz, Chloroform-d) δ 7.50 (t, J = 4.6 Hz, 1H), 7.38 (dd, J = 7.5, 1.6 Hz, 1H), 7.34 (s, 1H), 7.13 (t, J = 7.5 Hz, 1H), 7.07 (dd,J = 7.5, 1.6 Hz, 1H), 5.04 (dd, J = 7.1, 4.4 Hz, 1H), 4.96 (dd, J = 7.1, 4.8Hz, 1H).

[0025] 2. Synthesis of compound B: ; Add 100mmol compound A, 20mmol glacial acetic acid, and 250g ethanol to the reaction bottle, start stirring, protect with nitrogen, raise the temperature to 60-70℃, and start to control the temperature to drip cyclohexanone ethanol solution (100mmol cyclohexanone dissolved in 30g ethanol). After the dropwise addition is completed, keep the temperature at 60-70℃ and keep warm until there is no compound cyclohexanone remaining after TLC tracking detection, add 100g toluene to extract and control the temperature at 60-70℃. Use tap water to wash the organic phase until it is neutral. After washing, add anhydrous sodium sulfate to dry the organic phase. The dried organic phase is passed through a silica gel column at normal pressure. After the column is passed, wash the column with 200g toluene each time, and wash it 3 times in total. After the elution is completed, combine the eluent and the column liquid and remove the solvent under negative pressure. After the solvent is removed, recrystallize with toluene to obtain 23g compound B with a yield of 80%. Mass spectrum: 287.0.

[0026] Hydrogen spectrum: 1H NMR (500 MHz, Chloroform-d) δ 7.33 (d, J = 7.5 Hz, 1H), 7.15 (d, J = 7.6 Hz, 1H), 4.18 (d, J = 9.0 Hz, 1H), 4.10 (dq, J = 9.1, 7.1 Hz,1H), 2.88 (q, J = 7.0 Hz, 1H),1.86 – 1.45 (m, 8H).

[0027] 3. Synthesis of compound C: ; Add 100mmol of compound B and 300g of toluene to the reaction bottle, start stirring, protect with nitrogen, heat to 20-30℃, and add 300mmol of DDQ under temperature control. After adding, keep warm for reaction. After TLC tracking detection shows that there is no compound B left, filter the reaction solution and rinse the filter cake with 100g of toluene. After elution, pass the organic phase of the filtrate through a silica gel column at normal pressure. After the column is passed, rinse the column with 200g of toluene each time, for a total of 3 times. After elution, combine the eluent and the column liquid and remove the solvent under negative pressure. After removing the solvent, recrystallize with toluene to obtain 16.8g of compound C with a yield of 60%. Mass spectrum: 280.9.

[0028] Hydrogen spectrum: 1 H NMR (500 MHz, Chloroform-d) δ 10.42 (s, 1H), 8.14 (dd, J =7.5, 1.6 Hz, 1H), 7.88 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 7.5 Hz, 1H), 7.42(dd, J = 7.7, 1.8 Hz, 1H), 7.29 (td, J = 7.5, 1.8 Hz, 1H), 7.24 (td, J = 7.3, 1.6 Hz, 1H).

[0029] 4. Synthesis of Compound D: ; 100mmol compound C, 250mmol potassium carbonate, 150g toluene and 80g purified water were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol tetrakistriphenylphosphine palladium was added to the reaction flask, the temperature was raised to 60-70℃, and 2-nitrobenzeneboric acid / THF solution (100mmol phenylboric acid was dissolved in 50gTHF) was added dropwise. After the addition was completed, the reaction was kept warm. After TLC tracking and detection, no compound C remained, the mixture was allowed to stand and the layers were separated. The aqueous phase in the reaction system was separated, and then the temperature was controlled at 30-40℃ and the organic phase was washed with tap water until neutral. After the washing was completed, anhydrous sodium sulfate was added to dry the organic phase, and the dried organic phase was passed through a silica gel column at normal pressure. After the column was passed, 200g toluene was used to elute the column each time, and the eluent was rinsed 3 times in total. After the elution was completed, the eluent and the column liquid were combined and the solvent was removed under negative pressure. After the solvent was removed, it was recrystallized with toluene to obtain 22.5g compound D with a yield of 70%. Mass spectrum: 322.1.

[0030] Hydrogen spectrum: 1 H NMR (500 MHz, Chloroform-d) δ 10.65 (s, 1H), 8.15 (dd, J =7.3, 1.6 Hz, 1H), 8.12 – 8.07 (m, 1H), 7.98 (d, J = 7.6 Hz, 1H), 7.80 (dd, J= 7.3, 1.6 Hz, 1H), 7.70 – 7.63 (m, 2H), 7.59 (td, J = 7.5, 1.6 Hz, 1H), 7.43 (dd, J = 7.5, 1.7 Hz, 1H), 7.33 (td, J = 7.3, 1.6 Hz, 1H), 7.23 (td, J = 7.5,1.6 Hz, 1H).

[0031] 5. Synthesis of Compound E: ; Add 100mmol compound D, 1000mmol PTE, and 300g ODB to the reaction bottle, start stirring, protect with nitrogen, heat to 170-180℃, and after TLC tracking and detection, remove the compound D under negative pressure until the theoretical amount of the product is 1-2 times of the remaining ODB, then cool to 60-70℃, add 300g toluene for extraction, and wash the organic phase with tap water until it is neutral. After washing, add anhydrous sodium sulfate to dry the organic phase, and the dried organic phase is passed through a silica gel column at normal pressure. After the column is passed, rinse the column with 200g toluene each time, and rinse 3 times in total. After elution, combine the eluent and the column liquid and remove the solvent under negative pressure. After the solvent is dried, recrystallize with toluene to obtain 11.5g compound E, with a yield of 40%. Mass spectrum: 290.1.

[0032] Hydrogen spectrum: 1 H NMR (500 MHz, Chloroform-d) δ 10.66 (d, J = 16.7 Hz, 2H),8.05 (dd, J = 7.6, 1.6 Hz, 1H), 7.96 – 7.89 (m, 1H), 7.47 – 7.38 (m, 3H),7.38 –7.29 (m, 3H), 7.23 (td, J = 7.5, 1.6 Hz, 1H).

[0033] 6. Synthesis of Compound F: ; 100mmol compound E, 110mmol pinacol diboronate, 300mmol potassium acetate, 1mmol Pd2(dba)3, 2mmol S-PHOS (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl), 1mmol LiBr, 200g toluene were added to the reaction bottle, stirring was started, nitrogen protection was applied, the temperature was raised to 100-110℃, after TLC tracking detection showed that there was no compound E remaining, the temperature was lowered to 60-70℃, the organic phase was washed with tap water until neutral, after the washing was completed, anhydrous sodium sulfate was added to dry the organic phase, the dried organic phase was passed through a silica gel column at normal pressure, after the column was passed, 200g toluene was used to elute the column each time, for a total of 3 times. After the elution was completed, the eluent and the column liquid were combined and the solvent was removed under negative pressure, after the solvent was removed, it was recrystallized with toluene to obtain 27.5g compound F, with a yield of 72%. Mass spectrum: 382.2.

[0034] Hydrogen spectrum: 1 H NMR (500 MHz, Chloroform-d) δ 10.76 (s, 1H), 10.67 (s, 1H), 8.00 (dd, J = 7.5, 1.5 Hz, 1H), 7.89 – 7.84 (m, 1H), 7.46 (s, 1H), 7.42 (dd,J =7.5, 1.8 Hz, 2H), 7.35 – 7.25 (m, 3H), 7.21 (td, J = 7.5, 1.6 Hz, 1H), 1.24 (s, 12H).

[0035] 7. Synthesis of Compound G ; 102mmol 4-bromo-5-fluoroquinoline, 250mmol potassium carbonate, 80g purified water, and 250g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol tetrakistriphenylphosphine palladium was added to the reaction flask, the temperature was raised to 60-70°C, and the compound F / THF solution (100mmol compound F was dissolved in 200g THF) was added dropwise under temperature control. After the addition was completed, the reaction was kept warm. After TLC tracking and detection showed that there was no compound F remaining, the mixture was allowed to stand and the layers were separated. The aqueous phase in the reaction system was separated, and then the temperature was controlled at 60-70°C and the organic phase was washed with tap water until it was neutral. After the washing was completed, anhydrous sodium sulfate was added to dry the organic phase. The dried organic phase was passed through a silica gel column at normal pressure. After the column was passed, 200g toluene was used to elute the column each time, and the column was eluted 3 times in total. After the elution was completed, the eluent and the column liquid were combined and the solvent was removed under negative pressure. After the solvent was removed, it was recrystallized from toluene to obtain 28.5g compound C with a yield of 71%. Mass spectrum: 401.1.

[0036] Hydrogen spectrum: 1 H NMR (500 MHz, Chloroform-d) δ 11.28 (s, 1H), 10.37 (s, 1H), 8.86 (dd, J = 7.2, 1.5 Hz, 1H), 8.82 (d, J = 7.5 Hz, 1H), 8.02 (dd, J = 7.7,1.5 Hz, 1H), 7.97 (dd, J =7.5, 1.6 Hz, 1H), 7.77 (d, J = 7.5 Hz, 1H), 7.58(td, J = 7.3, 5.0 Hz, 1H), 7.47 (s, 1H), 7.39 (dd, J = 7.5, 1.7 Hz, 2H), 7.31(td, J = 7.3, 1.4 Hz, 2H), 7.23 (ddd, J = 14.7, 7.5, 1.6 Hz, 2H), 7.19 (dd, J= 7.5, 1.6 Hz, 1H).

[0037] 8. Synthesis of the matrix: ; 100mmol compound G, 300mmol potassium carbonate, 200g DMF were added to the reaction bottle, stirring was started, nitrogen protection was applied, the temperature was raised to 140-150℃ and kept warm, after TLC tracking and detection of no compound G remaining, the temperature was lowered to room temperature and filtered, the filtrate was retained, and the solvent was removed under negative pressure to obtain a black oily substance, 400g toluene was added and the temperature was raised to 50-60℃ and completely dissolved, the temperature was controlled at 50-60℃, and the organic phase was washed with tap water until neutral, anhydrous sodium sulfate was added to dry the organic phase after washing, and the silica gel column was passed under normal pressure. After the column was passed, 200g toluene was used to rinse the column each time, and the total elution was 3 times. After the elution was completed, the elution liquid and the column liquid were combined and the solvent was removed under negative pressure. After the solvent was removed, 22.9g of the parent compound was recrystallized from toluene, with a yield of 60%. Mass spectrum: 381.1.

[0038] Hydrogen spectrum: 1 H NMR (500 MHz, Chloroform- d ) δ 10.14 (s, 1H), 8.93 (d, J = 7.5Hz, 1H), 8.86 (dd, J = 7.3, 1.5 Hz, 1H), 8.62 (dd, J = 7.1, 1.6 Hz, 1H), 8.49 (d, J = 7.5 Hz, 1H), 8.21 – 8.16 (m, 1H), 7.70 – 7.56 (m, 2H), 7.53 (dd, J = 7.3,1.4 Hz, 1H), 7.50 – 7.41 (m, 2H), 7.39 (dd, J = 7.3, 1.4 Hz, 1H), 7.37 – 7.29(m, 3H).

[0039] Example 1 Preparation of compound [3-1]: ; 100mmol of the parent, 102mmol of fluorobenzene, 300mmol of potassium carbonate, and 400g of DMF were added to the reaction bottle, stirred, protected by nitrogen, and heated to 140-150℃ for preservation. After TLC tracking and detection of no residual compound, the temperature was cooled to room temperature and filtered. The filtrate was retained and the solvent was removed under negative pressure to obtain a black oily substance. 500g of toluene was added and heated to 60-70℃ for complete dissolution. The organic phase was washed with tap water to neutrality at a temperature of 60-70℃. After washing, anhydrous sodium sulfate was added to dry the organic phase, and the silica gel column was passed under normal pressure. After the column was passed, 200g of toluene was used to rinse the column each time, and the elution was performed 3 times in total. After the elution was completed, the eluent and the column liquid were combined and the solvent was removed under negative pressure. After the solvent was removed, 32.5g of compound [3-1] was recrystallized from toluene, with a yield of 71%. Mass spectrum: 457.2.

[0040] Hydrogen spectrum: 1 H NMR (500 MHz, Chloroform-d) δ 8.87 (d, J = 7.5 Hz, 1H), 8.62 (dd, J = 7.5, 1.2 Hz, 1H), 8.40 (d, J = 7.5 Hz, 1H), 8.12 (dd, J = 7.2, 1.9Hz, 1H), 8.01 – 7.94 (m, 1H), 7.73 (t, J = 7.5 Hz, 1H), 7.66 (dd, J =7.0, 1.8Hz, 1H), 7.63 – 7.56 (m, 1H), 7.55 – 7.49 (m, 3H), 7.49 – 7.43 (m, 3H), 7.39– 7.29 (m, 5H).

[0041] Example 2 Preparation of compound [3-9]: ; 100mmol of the parent, 102mmol of 1-fluoronaphthalene, 300mmol of potassium carbonate, and 400g of DMF were added to the reaction bottle, stirred, protected by nitrogen, and heated to 140-150℃ for preservation. After TLC tracking and detection of no residual compound, the temperature was cooled to room temperature and filtered. The filtrate was retained and the solvent was removed under negative pressure to obtain a black oily substance. 600g of toluene was added and heated to 60-70℃ for complete dissolution. The organic phase was washed with tap water to neutrality at a temperature of 60-70℃. After washing, anhydrous sodium sulfate was added to dry the organic phase, and the silica gel column was passed under normal pressure. After the column was passed, 200g of toluene was used to rinse the column each time, and the elution was performed 3 times in total. After the elution was completed, the eluent and the column liquid were combined and the solvent was removed under negative pressure. After the solvent was removed, 37.5g of compound [3-9] was recrystallized from toluene, with a yield of 74%. Mass spectrum: 507.2.

[0042] Hydrogen spectrum: 1 H NMR (500 MHz, Chloroform-d) δ 8.87 (d, J = 7.1 Hz, 1H), 8.62 (dd, J = 7.5, 1.2 Hz, 1H), 8.40 (d, J = 7.5 Hz, 1H), 8.17 (dd, J = 7.6, 1.5Hz, 1H), 8.01 (dd, J =7.5, 1.9 Hz, 1H), 7.99 – 7.90 (m, 2H), 7.82 – 7.73 (m,2H), 7.64 (ddd, J = 14.0, 7.3, 1.7 Hz, 2H), 7.57 – 7.29 (m, 10H).

[0043] Example 3 Preparation of compound [3-37]: (1) Synthesis of compound H: ; 100mmol of the parent, 102mmol of p-bromofluorobenzene, 300mmol of potassium carbonate, and 400g of DMF were added to the reaction bottle, stirred, protected by nitrogen, and heated to 140-150℃ for insulation. After TLC tracking and detection of no compound remaining, the temperature was cooled to room temperature and filtered. The filtrate was retained and the solvent was removed under negative pressure to obtain a black oily substance. 500g of toluene was added and heated to 60-70℃ for complete dissolution. The organic phase was washed with tap water to neutrality at a temperature of 60-70℃. After washing, anhydrous sodium sulfate was added to dry the organic phase, and the silica gel column was passed under normal pressure. After the column was passed, 200g of toluene was used to elute the column each time, and the column was rinsed 3 times in total. After the elution was completed, the eluent and the column liquid were combined and the solvent was removed under negative pressure. After the solvent was removed, 37.5g of compound H was recrystallized from toluene, with a yield of 70%. Mass spectrum: 535.1.

[0044] Hydrogen spectrum: 1 H NMR (500 MHz, Chloroform-d) δ 8.86 (d, J = 7.5 Hz, 1H), 8.62 (dd, J = 7.5, 1.2 Hz, 1H), 8.40 (d, J = 7.5 Hz, 1H), 8.17 (dd, J = 7.7, 1.5Hz, 1H), 8.01 – 7.92 (m, 2H), 7.64 (ddd, J = 17.5, 7.1, 1.5 Hz, 2H), 7.54 – 7.48 (m, 3H), 7.47 (s, 1H), 7.42 – 7.27 (m, 6H).

[0045] (2) Synthesis of compound [3-37]: ; 100mmol compound H, 250mmol potassium carbonate, 500g toluene and 80g purified water were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol tetrakistriphenylphosphine palladium was added to the reaction flask, the temperature was raised to 60-70℃, and 3-boric acid-9,9-dimethylfluorene / THF solution (100mmol 3-boric acid-9,9-dimethylfluorene dissolved in 120gTHF) was added dropwise. After the addition was completed, the reaction was kept warm. After TLC tracking and detection of no compound H remaining, the reaction was allowed to stand and the layers were separated. The aqueous phase in the reaction system was separated, and then the organic phase was washed with tap water at 30-40℃ until it was neutral. After the washing was completed, anhydrous sodium sulfate was added to dry the organic phase, and the dried organic phase was passed through a silica gel column at normal pressure. After the column was passed, 200g toluene was used to rinse the column each time, and the elution was performed 3 times in total. After elution, the eluent and column liquid were combined and the solvent was removed under negative pressure. After the solvent was removed, it was recrystallized from toluene to obtain 50.6 g of compound [3-37] with a yield of 78%. Mass spectrum: 649.3.

[0046] Hydrogen spectrum: 1 H NMR (500 MHz, Chloroform-d) δ 8.85 (d, J = 7.5 Hz, 1H), 8.62 (dd, J = 7.5, 1.2 Hz, 1H), 8.40 (d, J = 7.5 Hz, 1H), 8.17 (dd, J = 7.7, 1.5Hz, 1H), 8.02 – 7.92 (m, 2H), 7.84 (d, J = 1.5 Hz, 1H), 7.73 – 7.68 (m, 2H), 7.65 (dd, J = 7.5, 1.6 Hz, 1H), 7.63 – 7.29 (m, 14H), 7.26 (d, J = 7.7 Hz, 1H), 1.55 (s, 6H).

[0047] The synthesis methods of other compounds were the same, and the raw materials of each compound were different. The FD-MS data of compounds [3-1] to [3-46] are shown in Table 1.

[0048] Table 1 Summary of FD-MS data of compounds [3-1] to [3-46]

[0049] The application effects of the compounds of the present invention on OLED devices are described in detail below through application examples and application comparison examples.

[0050] Organic light-emitting device preparation: Preparation of ITO (indium tin oxide) glass substrate: Place an ITO glass substrate with a film thickness of 150nm in distilled water for ultrasonic cleaning for 20 minutes, then use isopropyl alcohol, acetone, and methanol for ultrasonic cleaning for 10 minutes each in sequence, dry, transfer to a plasma cleaning machine, wash the above substrate for 5 minutes, perform UV-Ozone treatment (ultraviolet light ozone treatment), and finally send it to a vacuum evaporator.

[0051] Hole injection layer: 2-TNATA was evaporated on the ITO glass substrate using a vacuum evaporator at a evaporation rate of 1Å / s, and the coating thickness was 10nm.

[0052] Hole transport layer: a-NPD was evaporated on the hole injection layer using a vacuum evaporator at a deposition rate of 1.5Å / s, and the coating thickness was 60nm.

[0053] Light-emitting layer: The main material and the dopant material are evaporated on the hole transport layer using a vacuum evaporator at an evaporation rate of 1Å / s. The coating thickness is 25nm, wherein the evaporation rate ratio of the main material to the dopant material is 95:5. The composition of the main material and the dopant material is shown in Table 2 below: Table 2 Composition of main materials and doping materials of the light-emitting layer

[0054] Electron transport layer: Liq was evaporated on the light-emitting layer using a vacuum evaporator at a evaporation rate of 1Å / s, and the coating thickness was 30nm.

[0055] Electron injection layer and cathode: Lithium fluoride (LiF) was deposited on the electron transport layer using a vacuum evaporator at a deposition rate of 0.5Å / s, with a coating thickness of 1nm. Then, an aluminum layer with a thickness of 80nm was deposited at a deposition rate of 1Å / s as the cathode.

[0056] Packaging: The evaporated substrate and cover are pressed together, and then packaged with ultraviolet curing resin (or UV glue light curing) in a nitrogen glove box.

[0057] The structures of the compounds involved in the above application examples and comparative examples are as follows: ; ; .

[0058] The current, voltage and luminescence characteristics of the obtained organic electroluminescent device were characterized by characterization equipment, and the driving voltage, color coordinates, efficiency and life of each device were recorded. The characterization results are shown in Table 3, where the following comparative examples and application example devices were tested under the same external environment and the same brightness (1000nit).

[0059] Table 3 Luminous characteristics test results (1000nit)

[0060] From the data in Table 3, it can be seen that the compounds of the present invention have good green light base color purity and have high luminous efficiency and long service life. Because the parent structure of the present invention is a six-membered rigid condensed ring structure formed by indolecarbazole and quinoline, it contains quinoline and indolecarbazole heterocyclic basic knots, has a strong electron-donating and electron-withdrawing effect between molecules, has a large steric hindrance, and the π-π conjugated effect between the six-membered rings formed by the indolecarbazole and quinoline structures makes it easier for electrons to transition from the ground state to the excited state, and releases more efficient energy when returning to the ground state. The final device achieves efficient green light emission, which significantly improves the device's luminous efficiency and life.

[0061] The organic light-emitting device prepared from the indolecarbazole and quinoline organic compound of the present invention can obtain good green light color purity, high luminous efficiency and long service life, and thus obtains a good market space in the OLED industry. The organic light-emitting device of the present invention can be applied to multiple industries such as televisions, computers, automobiles, watches, printers, etc., has a wide range of applications, and the device has strong applicability, which promotes the development of the industry in a better and broader direction.

[0062] The technical features of the above-described embodiments may be arbitrarily combined. To make the description concise, not all possible combinations of the technical features in the above-described embodiments are exhaustively listed. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0063] For those skilled in the art, several modifications and improvements may be made without departing from the concept of the present invention, all of which belong to the protection scope of the present invention. The protection scope of the present invention shall be based on the attached claims.

Claims

1. An indolecarbazole-quinoline compound, characterized in that: The structure of the indolecarbazole-quinoline compound is shown in the following general formula [I]: General formula [I]; In the general formula [I], R represents a substituted or unsubstituted C6-C20 aryl or heterocyclic aryl group, wherein the substituent is selected from at least one of deuterium, phenyl, and alkyl; and the heteroatom in the heterocyclic aryl group is selected from at least one of O, N, and S.

2. An indolecarbazoquinoline compound according to claim 1, characterized in that: The R is selected from substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, pyrenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, carbazolyl, fluorenyl; The substituent is selected from at least one of deuterium, phenyl, and C1-C3 alkyl.

3. An indolecarbazoquinoline compound according to claim 1, characterized in that: The R is selected from any one of the following group structures: 。 4. An indolecarbazoquinoline compound according to claim 1, characterized in that: The indolecarbazole-quinoline compound is selected from any one of the following structures: 。 5. An organic electroluminescent device, characterized in that: The indolecarbazole-quinoline compound according to any one of claims 1 to 4 is used in an organic electroluminescent device.

6. An organic electroluminescent device according to claim 5, characterized in that: The organic layer of the organic electroluminescent device comprises at least one of the indolecarbazole and quinoline compounds.

7. An organic electroluminescent device according to claim 6, characterized in that: The organic layer of the organic electroluminescent device includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

8. The organic electroluminescent device according to claim 5, characterized in that: The indolecarbazole-quinoline compound is applied to the light-emitting layer of an organic electroluminescent device.

9. An organic electroluminescent device according to claim 8, characterized in that: The indolecarbazole and quinoline compounds are used as the main material of the light-emitting layer of an organic electroluminescent device.

10. An electronic device, characterized in that: The electronic device comprises the organic electroluminescent device according to any one of claims 5 to 9.

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