An indolocarbazole-quinoline compound and its application

Abstract

The present invention relates to the technical field of organic electroluminescent materials, and particularly relates to an indolocarbazole-quinoline compound and its application. The structure of the indolocarbazole-quinoline compound is as follows:; R represents a substituted or unsubstituted aryl or heteroaryl group having 6 to 20 carbon atoms, wherein the substituent is selected from at least one of deuterium, phenyl, and alkyl; the heteroatom in the heteroaryl group is selected from at least one of O, N, and S. The parent structure of the indolocarbazole-quinoline compound of the present invention is a six-membered ring rigid fused ring structure, which contains quinoline and indolocarbazole heterocyclic basic structures, has a strong electron-donating and electron-withdrawing effect between molecules, has a large steric hindrance, and the π-π conjugation effect between the six-membered rings formed by the indolocarbazole 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 organic electroluminescent device applied has high luminous efficiency and long lifespan.

Description

Technical Field

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

[0002] As the third-generation display material, the status of OLED is constantly rising in the display field. The demand for OLED display materials is gradually increasing in more and more industries. As the three basic light-emitting materials of OLED: red light material, green light material, and blue light material, with the continuous progress of the chemical industry and manufacturing industry, the types of OLED materials tend to be diversified.

[0003] Among them, the green light material is one of the key components of OLED materials. The existing green light materials with high efficiency, fast response, and low cost are required for market applications. The development of good green light materials has become an important breakthrough difficulty. Excellent green light materials, due to their short wavelength and high frequency, have strong anti-interference ability to the outside world, enabling electrons to efficiently transition from the ground state to the excited state, and showing 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. The emergence of ultra-high definition and 4K pictures has a stronger demand for high-quality green light, and the color level and fineness need to be better transitioned. Good color purity has become the key breakthrough point for green light materials. Different from red and blue light materials, green light materials are affected by broadening or shoulder peaks, resulting in large fluctuations in their CIE coordinates and significant changes in color purity, greatly reducing their own luminous efficiency and service life. High-efficiency green light has a broader market prospect.

[0005] The continuous innovation and development of green light materials have enabled OLED technology to bloom in multiple fields such as wearables and vehicles. High-efficiency green light requires more mature technology and better cost to meet market demands. It injects a more vital source into the display field and, with the strong support of the country, provides a more solid guarantee for the display field. Developing 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 of the existing technology, the present invention provides an indolocarbazole-quinoline compound and its application. The indolocarbazole-quinoline compound is applied to an OLED device, has good green primary color purity, and can significantly improve the luminous efficiency and service life of the device.

[0007] The technical solution for the present invention to solve the above technical problems is as follows: An indolocarbazole-quinoline compound, and the structure of the indolocarbazole-quinoline compound is shown as the following general formula [I]:

[0008] General formula [I];

[0009] In general formula [I], R represents a substituted or unsubstituted aryl or heteroaryl group having 6 to 20 carbon atoms, wherein the substituent is selected from at least one of deuterium, phenyl, and alkyl; the heteroatoms in the heteroaryl group are selected from at least one of O, N, and S.

[0010] Furthermore, R is selected from a substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, pyrenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, carbazolyl, and fluorenyl;

[0011] The substituent is selected from at least one of deuterium, phenyl, and C1-C3 alkyl.

[0012] Furthermore, R is selected from any one of the following group structures:

[0013] 。

[0014] Furthermore, the indolocarbazole quinoline compounds are selected from any one of the following structures:

[0015] 。

[0016] The present invention also discloses an organic electroluminescent device, in which the indolocarbazole quinoline compound is applied to the organic electroluminescent device.

[0017] Furthermore, at least one of the indolocarbazole quinoline compounds is included in the organic layer of the organic electroluminescent device.

[0018] 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.

[0019] Furthermore, the indolocarbazole quinoline compound is applied to the light-emitting layer of the organic electroluminescent device.

[0020] Furthermore, the indolocarbazole quinoline compound is used as a host material for the light-emitting layer of the organic electroluminescent device.

[0021] Furthermore, the indolocarbazole quinoline compound is used as a light-emitting material in OLED lighting and OLED display panels, and the light-emitting material is used singly or after doping in one or more of a red light-emitting material, a green light-emitting material, and a blue light-emitting material.

[0022] The present invention also discloses an electronic device, characterized in that the electronic device includes the organic electroluminescent device of the present invention.

[0023] The beneficial effects of the present invention are as follows:

[0024] The parent structure of the indolocarbazole-quinoline compound of the present invention is a six-membered ring rigid fused ring structure formed by indolocarbazole and quinoline. It contains quinoline and indolocarbazole heterocyclic basic structures, has a strong electron-donating and electron-withdrawing effect between molecules, has a relatively large steric hindrance, and the π-π conjugation effect between the six-membered rings formed by the indolocarbazole and quinoline structures enables electrons to better transition from the ground state to the excited state, and releases more efficient energy when returning to the ground state. Finally, the device realizes efficient green light emission, significantly improving the luminous efficiency and lifespan of the device.

[0025] The luminous efficiency and working lifespan characteristics of the OLED organic light-emitting device prepared from the indolocarbazole-quinoline compound provided by the present invention are significantly improved, and the stability is relatively good.

[0026] The organic light-emitting device made of the indolocarbazole-quinoline compound provided by the present invention can be applied to the OLED industry with high practicality, surface-emitting OLED light-emitting bodies for lighting, flexible light-emitting bodies, etc., and has good application prospects. Specific Embodiments

[0027] The following makes a detailed description of the specific embodiments of the present invention. The present invention can be implemented in many other ways different from those described herein. Those skilled in the art can make similar improvements without departing from the connotation of the present invention. Therefore, the present invention is not limited by the specific embodiments disclosed.

[0028] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the technical field to which the present invention belongs. The terms used are only for describing specific embodiments and do not limit the present invention.

[0029] I. Preparation Examples

[0030] Synthesis of the Parent

[0031] 1. Synthesis of Compound A:

[0032] ;

[0033] 100 mmol of compound 3-bromo-2-chloroaniline and 100 g of acetonitrile were added to a reaction flask. Stirring was started and the mixture was protected by nitrogen. The temperature was raised to 20 - 30 °C and 600 mmol of hydrochloric acid was added dropwise while controlling the temperature. After the addition was complete, the mixture was kept at the same temperature for 1 h, then cooled to 0 - 10 °C, and 150 mmol of an aqueous sodium nitrite solution (prepared by dissolving 150 mmol of sodium nitrite in 30% aqueous solution) was added dropwise while controlling the temperature. After the addition was complete and the mixture was kept at the same temperature for 1 h, the prepared reaction solution was added dropwise to a hydrochloric acid solution of stannous chloride (prepared by dissolving 200 mmol of stannous chloride and 500 mmol of hydrochloric acid) at 0 - 10 °C. After the addition was complete and the mixture was kept at the same temperature for 1 h, the temperature was raised to 20 - 30 °C and kept at this temperature for 3 h. Post-treatment was carried out. The reaction solution was filtered, and the filter cake was slurried with toluene to obtain 20.6 g of compound A with a yield of 80%. Mass spectrum: 257.9.

[0034] Proton NMR 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).

[0035] 2. Synthesis of compound B:

[0036] ;

[0037] 100 mmol of compound A, 20 mmol of glacial acetic acid, and 250 g of ethanol were added to a reaction flask. Stirring was started and the mixture was protected by nitrogen. The temperature was raised to 60 - 70 °C, and an ethanol solution of cyclohexanone (100 mmol of cyclohexanone dissolved in 30 g of ethanol) was added dropwise while controlling the temperature. After the addition was complete, the mixture was kept at 60 - 70 °C and monitored by TLC until no cyclohexanone remained. Then 100 g of toluene was added for extraction, and the organic phase was washed with tap water at 60 - 70 °C until neutral. After washing, anhydrous sodium sulfate was added to dry the organic phase. The dried organic phase was passed through a silica gel column under normal pressure. After passing through the column, the column was rinsed with 200 g of toluene each time, and rinsing was carried out 3 times in total. After rinsing, the rinsing solution and the solution passing through the column were combined and the solvent was removed under reduced pressure. After the solvent was removed, the residue was recrystallized with toluene to obtain 23 g of compound B with a yield of 80%. Mass spectrum: 287.0.

[0038] Proton NMR spectrum: 11H 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).

[0039] 3. Synthesis of Compound C:

[0040] ;

[0041] Add 100 mmol of Compound B and 300 g of toluene into a reaction flask, start stirring, protect with nitrogen, heat up to 20 - 30 °C, and add 300 mmol of DDQ while controlling the temperature. After the addition is complete, keep the reaction at a constant temperature. After TLC tracking shows no remaining Compound B, filter the reaction solution, and wash the filter cake with 100 g of toluene. After the washing is complete, pass the organic phase of the filtrate through a silica gel column at atmospheric pressure. After the column passing is complete, wash the column with 200 g of toluene each time, for a total of 3 times. After the washing is complete, combine the washing solution and the column passing solution and remove the solvent under reduced pressure. After removing the solvent, recrystallize with toluene to obtain 16.8 g of Compound C, with a yield of 60%. Mass spectrum: 280.9.

[0042] Hydrogen spectrum: 1 1H 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).

[0043] 4. Synthesis of Compound D:

[0044] ;

[0045] Add 100 mmol of Compound C, 250 mmol of potassium carbonate, 150 g of toluene and 80 g of purified water into a reaction flask. Start stirring under nitrogen protection, and then add 1 mmol of tetrakis(triphenylphosphine)palladium into the reaction flask. Heat up to 60 - 70 °C and start temperature control to dropwise add the 2-nitrophenylboronic acid / THF solution (100 mmol of phenylboronic acid dissolved in 50 g of THF). After the addition is complete, keep the temperature for reaction. After TLC tracking shows no remaining Compound C, let it stand for phase separation, separate the aqueous phase in the reaction system, and then wash the organic phase with tap water to neutral at 30 - 40 °C. After the washing is complete, add anhydrous sodium sulfate to dry the organic phase. The dried organic phase is passed through a silica gel column under normal pressure. After passing through the column, wash the column with 200 g of toluene each time, and wash 3 times in total. After the washing is complete, combine the eluate and the column-passed liquid and remove the solvent under negative pressure. After removing the solvent, recrystallize with toluene to obtain 22.5 g of Compound D, with a yield of 70%. Mass spectrum: 322.1.

[0046] 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).

[0047] 5. Synthesis of Compound E:

[0048] ;

[0049] Add 100 mmol of compound D, 1000 mmol of PTE, and 300 g of ODB into a reaction flask. Start stirring and protect with nitrogen. Heat up to 170 - 180 °C. After TLC tracking shows no remaining compound D, control the temperature below 180.0 °C and perform vacuum distillation until the remaining product is 1 - 2 times the theoretical amount of ODB. Then cool down to 60 - 70 °C and add 300 g of toluene for extraction. Wash the organic phase with tap water until neutral. After washing, add anhydrous sodium sulfate to dry the organic phase. The dried organic phase is passed through a silica gel column under normal pressure. After passing through the column, wash the column with 200 g of toluene each time, for a total of 3 times. After washing, combine the eluent and the column-passing solution and vacuum dry the solvent. After drying the solvent, recrystallize with toluene to obtain 11.5 g of compound E, with a yield of 40%. Mass spectrum: 290.1.

[0050] 1H NMR 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).

[0051] 6. Synthesis of compound F:

[0052] ;

[0053] Add 100 mmol of compound E, 110 mmol of bis(pinacolato)diboron, 300 mmol of potassium acetate, 1 mmol of Pd2(dba)3, 2 mmol of S-PHOS (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl), 1 mmol of LiBr, and 200 g of toluene into a reaction flask. Start stirring and protect with nitrogen. Heat up to 100 - 110 °C. After TLC tracking shows no remaining compound E, cool down to 60 - 70 °C and wash the organic phase with tap water until neutral. After washing, add anhydrous sodium sulfate to dry the organic phase. The dried organic phase is passed through a silica gel column under normal pressure. After passing through the column, wash the column with 200 g of toluene each time, for a total of 3 times. After washing, combine the eluent and the column-passing solution and vacuum dry the solvent. After drying the solvent, recrystallize with toluene to obtain 27.5 g of compound F, with a yield of 72%. Mass spectrum: 382.2.

[0054] 1H NMR spectrum: 11H 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).

[0055] 7. Synthesis of Compound G

[0056] ;

[0057] Add 102 mmol of 4-bromo-5-fluoroquinoline, 250 mmol of potassium carbonate, 80 g of purified water, and 250 g of toluene into the reaction flask. Start stirring and protect with nitrogen. Then add 1 mmol of tetrakis(triphenylphosphine)palladium into the reaction flask, heat up to 60 - 70 °C, and control the temperature to dropwise add the Compound F / THF solution (100 mmol of Compound F dissolved in 200 g of THF). After the dropwise addition, keep the reaction at a constant temperature. After TLC tracking detection shows no remaining Compound F, let it stand for liquid separation, separate the aqueous phase in the reaction system, and then control the temperature at 60 - 70 °C to wash the organic phase with tap water until neutral. After the water washing is completed, add anhydrous sodium sulfate to dry the organic phase. After drying, the organic phase is passed through a silica gel column under normal pressure. After the column passing is completed, wash the column with 200 g of toluene each time, and wash 3 times in total. After the washing is completed, combine the eluate and the column-passing solution and remove the solvent under negative pressure. After removing the solvent, recrystallize with toluene to obtain 28.5 g of Compound C, with a yield of 71%. Mass spectrum: 401.1.

[0058] Hydrogen spectrum: 11H 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).

[0059] 8. Synthesis of the parent compound:

[0060] ;

[0061] Add 100 mmol of compound G, 300 mmol of potassium carbonate, and 200 g of DMF into a reaction flask. Start stirring and protect with nitrogen. Heat to 140 - 150 °C and keep the temperature. After TLC tracking shows no remaining compound G, cool to room temperature and filter. Keep the filtrate and remove the solvent under reduced pressure to obtain a black oily substance. Add 400 g of toluene and heat to 50 - 60 °C until completely dissolved. Control the temperature at 50 - 60 °C and wash the organic phase with tap water until neutral. After washing, add anhydrous sodium sulfate to dry the organic phase and filter through a silica gel column at atmospheric pressure. After column chromatography, wash the column with 200 g of toluene each time, for a total of 3 times. After washing, combine the eluate and the column eluent and remove the solvent under reduced pressure. After removing the solvent, recrystallize with toluene to obtain 22.9 g of the parent compound, with a yield of 60%. Mass spectrum: 381.1.

[0062] Hydrogen spectrum: 1 1H 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).

[0063] Example 1

[0064] Preparation of Compound [3-1]:

[0065] ;

[0066] 100 mmol of the parent compound, 102 mmol of fluorobenzene, 300 mmol of potassium carbonate, and 400 g of DMF were added to a reaction flask. Stirring was started, and the mixture was protected by nitrogen. The temperature was raised to 140 - 150 °C and maintained. After TLC tracking showed no remaining compound, the temperature was lowered to room temperature and the mixture was filtered. The filtrate was retained, and the solvent was removed under reduced pressure to obtain a black oil. 500 g of toluene was added, and the mixture was heated to 60 - 70 °C until completely dissolved. The organic phase was washed with tap water at 60 - 70 °C until neutral. After washing, anhydrous sodium sulfate was added to dry the organic phase, and the organic phase was passed through a silica gel column under normal pressure. After passing through the column, the column was rinsed with 200 g of toluene each time, and rinsing was carried out 3 times in total. After rinsing, the rinsing solution and the column eluate were combined and the solvent was removed under reduced pressure. After removing the solvent, the residue was recrystallized with toluene to obtain 32.5 g of Compound [3-1], with a yield of 71%. Mass spectrum: 457.2.

[0067] Proton NMR 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).

[0068] Example 2

[0069] Preparation of Compound [3-9]:

[0070] ;

[0071] 100 mmol of the parent compound, 102 mmol of 1-fluoronaphthalene, 300 mmol of potassium carbonate, and 400 g of DMF were added to a reaction flask. Stirring was initiated, and under nitrogen protection, the temperature was raised to 140 - 150 °C for heat preservation. After TLC tracking detected no remaining compound, the temperature was lowered to room temperature and then filtered. The filtrate was retained, and the solvent was removed under reduced pressure to obtain a black oil. After adding 600 g of toluene and heating to 60 - 70 °C for complete dissolution, the organic phase was washed with tap water at 60 - 70 °C until neutral. After washing, anhydrous sodium sulfate was added to dry the organic phase, and it was passed through a silica gel column at atmospheric pressure. After column chromatography, the column was eluted with 200 g of toluene each time, and it was eluted 3 times in total. After elution, the eluate and the column eluate were combined and the solvent was removed under reduced pressure. After removing the solvent, recrystallization with toluene gave 37.5 g of compound [3-9], with a yield of 74%. Mass spectrum: 507.2.

[0072] Proton NMR: 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).

[0073] Example 3

[0074] Preparation of compound [3-37]:

[0075] (1) Synthesis of compound H:

[0076] ;

[0077] Add 100 mmol of the parent compound, 102 mmol of p-bromofluorobenzene, 300 mmol of potassium carbonate, and 400 g of DMF to a reaction flask. Start stirring and protect with nitrogen. Heat to 140 - 150 °C and hold the temperature. After TLC tracking shows no remaining compound, cool to room temperature and filter. Retain the filtrate. Remove the solvent under reduced pressure to obtain a black oil. Add 500 g of toluene and heat to 60 - 70 °C until completely dissolved. Control the temperature at 60 - 70 °C and wash the organic phase with tap water until neutral. After washing, add anhydrous sodium sulfate to dry the organic phase. Filter through a silica gel column at atmospheric pressure. After column chromatography, wash the column with 200 g of toluene each time, for a total of 3 times. After washing, combine the eluent and the column eluate and remove the solvent under reduced pressure. After removing the solvent, recrystallize with toluene to obtain 37.5 g of compound H, with a yield of 70%. Mass spectrum: 535.1.

[0078] 1H NMR 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).

[0079] (2) Synthesis of compound [3-37]:

[0080] ;

[0081] 100 mmol of compound H, 250 mmol of potassium carbonate, 500 g of toluene and 80 g of purified water were added to a reaction flask. Stirring was started and the reaction was protected by nitrogen. Then, 1 mmol of tetrakis(triphenylphosphine)palladium was added to the reaction flask. The temperature was raised to 60 - 70 °C and a solution of 3-boronic acid-9,9-dimethylfluorene / THF (100 mmol of 3-boronic acid-9,9-dimethylfluorene dissolved in 120 g of THF) was added dropwise while controlling the temperature. After the addition was complete, the reaction was carried out under insulation. After TLC tracking detection showed no remaining compound H, the mixture was allowed to stand for phase separation, and the aqueous phase in the reaction system was separated. Then, the organic phase was washed with tap water to neutrality at a controlled temperature of 30 - 40 °C. After the washing was complete, anhydrous sodium sulfate was added to dry the organic phase. The dried organic phase was passed through a silica gel column under atmospheric pressure. After the column passing was complete, the column was rinsed with 200 g of toluene each time, and rinsing was carried out 3 times in total. After the rinsing was complete, the rinsing solution and the column passing solution were combined and the solvent was removed under reduced pressure. After the solvent was removed, recrystallization was carried out with toluene to obtain 50.6 g of compound [3-37], with a yield of 78%. Mass spectrum: 649.3.

[0082] 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).

[0083] The synthesis methods of other compounds are the same. There are differences in the raw materials of each compound. The FD-MS data of compounds [3-1] - [3-46] are shown in Table 1 below.

[0084] Table 1 Summary of FD-MS data of compounds [3-1] - [3-46]

[0085]

[0086] The application effects of the compounds described in the present invention on OLED devices are described in detail below through application examples and application comparative examples.

[0087] Preparation of organic light-emitting devices:

[0088] Preparation of ITO (Indium Tin Oxide) glass substrate: Place an ITO glass substrate with a film thickness of 150 nm in distilled water and ultrasonically clean it for 20 min. Then, ultrasonically wash it with isopropanol, acetone, and methanol in sequence for 10 min each, dry it, transfer it to a plasma cleaner, wash the above substrate for 5 min, perform UV-Ozone treatment (ultraviolet light ozone treatment), and finally send it to a vacuum evaporation coater.

[0089] Hole injection layer: Evaporate 2-TNATA on the ITO glass substrate using a vacuum evaporation coater at an evaporation rate of 1 Å / s, and the coating thickness is 10 nm.

[0090] Hole transport layer: Evaporate a-NPD on the hole injection layer using a vacuum evaporation coater at an evaporation rate of 1.5 Å / s, and the coating thickness is 60 nm.

[0091] Light-emitting layer: Evaporate the host material and the doping material on the hole transport layer using a vacuum evaporation coater at an evaporation rate of 1 Å / s, and the coating thickness is 25 nm. The evaporation rate ratio of the host material to the doping material is 95:5. The components of the host material and the doping material are shown in Table 2 below:

[0092] Table 2 Composition of the host material and the doping material in the light-emitting layer

[0093]

[0094] Electron transport layer: Evaporate Liq on the light-emitting layer using a vacuum evaporation coater at an evaporation rate of 1 Å / s, and the coating thickness is 30 nm.

[0095] Electron injection layer and cathode: Evaporate lithium fluoride (LiF) on the electron transport layer using a vacuum evaporation coater at an evaporation rate of 0.5 Å / s, and the coating thickness is 1 nm. Then, evaporate an aluminum layer with a thickness of 80 nm as the cathode at an evaporation rate of 1 Å / s.

[0096] Encapsulation: Press the evaporated substrate and the cover plate together, and encapsulate them with ultraviolet curable resin (or UV glue light curing) through a nitrogen glove box.

[0097] The chemical structures of the compounds involved in the above application examples and comparative examples are as follows:

[0098] ;

[0099] ;

[0100] 。

[0101] The current-voltage and luminescence characteristics of the obtained organic light-emitting devices are characterized by a characterization device, and the driving voltage, color coordinates, efficiency, and lifespan of each device are recorded. The characterization results are shown in Table 3. Among them, the following comparative example and application example devices are all tested under the same external environment and the same brightness (1000 nit).

[0102] Table 3 Luminescence Characteristics Test Results (1000 nit)

[0103]

[0104] It can be seen from the data in Table 3 that the compound of the present invention has good green primary color purity, high luminescence efficiency, and long service life. Because the parent structure of the present invention is a six-membered ring rigid condensed ring structure formed by indolocarbazole and quinoline, which contains the basic structures of quinoline and indolocarbazole heterocycles, has a strong electron-donating and electron-withdrawing effect between molecules, has a large steric hindrance, and the π-π conjugation effect between the six-membered rings formed by the indolocarbazole 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. Finally, the device realizes efficient green light emission, significantly improving the luminescence efficiency and lifespan of the device.

[0105] The organic light-emitting device prepared from the indolocarbazole and quinoline-based organic compound of the present invention can obtain good green primary color purity, high luminescence efficiency, and long service life, so it has good market space in the OLED industry. The organic light-emitting device of the present invention is applicable to multiple industry fields such as televisions, computers, automobiles, watches, printers, etc., with a wide application range, strong device applicability, and promoting the development of the industry field in a better and broader direction.

[0106] The technical features of the above-described embodiments can be combined arbitrarily. For the sake of brevity of description, all possible combinations of the technical features in the above-described embodiments are not exhaustively listed. However, as long as there is no contradiction in the combination of these technical features, it should be considered to be within the scope described in this specification.

[0107] For those of ordinary skill in the art, without departing from the concept of the present invention, several modifications and improvements can still be made, and these all belong to the protection scope of the present invention. The protection scope of the present invention is subject to the appended claims.

Claims

1. An indolocarbazole-quinoline compound, characterized in that, The structure of the indolocarbazole-quinoline compound is shown by the following general formula [I]: General formula [I]; In general formula [I], R is selected from a substituted or unsubstituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, anthryl group, pyrenyl group, benzofuranyl group, dibenzofuranyl group, benzothiophenyl group, dibenzothiophenyl group, carbazolyl group, fluorenyl group; wherein the substituent is selected from at least one of deuterium, phenyl group, C1-C3 alkyl group.

2. An indolocarbazole-quinoline compound, characterized in that, The structure of the indolocarbazole-quinoline compound is shown by the following general formula [I]: General formula [I]; In general formula [I], R is selected from any one of the following group structures: 。 3. An indolocarbazole quinoline compound, characterized in that The indolocarbazole-quinoline compound is selected from any one of the following structures: 。 4. An organic electroluminescent device, characterized in that, The indolocarbazole-quinoline compound according to any one of claims 1-3 is applied to an organic electroluminescent device.

5. An organic electroluminescent device according to claim 4, characterized in that, The organic layer of the organic electroluminescent device includes at least one of the indolocarbazole-quinoline compounds.

6. The organic electroluminescent device according to claim 5, wherein 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.

7. The organic electroluminescent device according to claim 4, characterized in that, The indolocarbazole-quinoline compound is applied to the light-emitting layer of the organic electroluminescent device.

8. An organic electroluminescent device according to claim 7, wherein, The indolocarbazole-quinoline compound is used as a host material for the light-emitting layer of the organic electroluminescent device.

9. An electronic device, characterized in that, The electronic device includes the organic electroluminescent device according to any one of claims 4-8.

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