9,10-dihydro-acridine derivative, and preparation method and use thereof

Abstract

The present invention discloses a 9,10-dihydro-acridine derivative having a structure of Formula (I). The compound has a suitable HOMO energy level that matches that of an anode and light emitting layer when used as a material of a hole transport layer, thus reducing the potential barrier needed to overcome when holes are transported to the light emitting layer, and reducing the operating voltage of the device. Moreover, the 9,10-dihydro-acridine derivative has high triplet energy level and LUMO level, to avoid the returning of energy from the light emitting layer, retain the electrons in the light emitting layer, increase the probability of recombination of electrons and holes in the light emitting layer, and enhance the luminescence efficiency of the device. The compound of Formula (I) has high glass transition temperature, good film forming performance, and high thermal stability. The present invention further discloses an organic light-emitting device having at least one functional layer containing the 9,10-dihydro-acridine derivative. When the compound is used as a material of the hole transport layer, a light-emitting device of high luminescence efficiency and low driving voltage is obtained.

Claims

1. A 9,10-dihydro-acridine derivative, having a structure of Formula (I): ##STR00215## wherein T is selected from O, S, C(R.sub.3)(R.sub.4) or N(R.sub.5); R.sub.1-R.sub.4 and R.sub.6-R.sub.7 are each independently selected from hydrogen; R.sub.5 is a C.sub.6-C.sub.60 substituted or unsubstituted aryl group; Ar.sub.1 is a C.sub.6-C.sub.60 substituted or unsubstituted aryl group; p is an integer from 1 to 5, q.sub.2 is an integer from 1 to 4, and q.sub.3 is an integer from 1 to 4; Ar.sub.3 and Ar.sub.4 are each independently selected from the following groups that are unsubstituted or substituted with 1-4 R.sub.1a: phenyl, biphenylyl, terphenylyl, fluorenyl; in which R.sub.1a is a C.sub.1-C.sub.6 alkyl group.

2. The 9,10-dihydro-acridine derivative according to claim 1, wherein Ar.sub.1 is selected from any of the following groups: phenyl, biphenylyl, terphenylyl, indenyl, fluorenyl, naphthyl, azulenyl, pentalenyl, heptalenyl, octalenyl, benzodiindenyl, acenaphthylenyl, phenalenyl, phenanthrenyl, anthracenyl, triindenyl, fluoranthenyl, acephenanthrenyl, aceanthrylenyl, 9,10-benzophenanthrenyl, pyrenyl, 1,2-benzophenanthrenyl, butylphenyl, naphthacenyl, pleiadenyl, picenyl, perylenyl, pentaphenyl, pentacenyl, tetraphenylene, cholanthrenyl, helicenyl, hexaphenyl, rubicenyl, coronenyl, trinaphthylenyl, heptaphenyl, pyranthrenyl, ovalenyl, corannulenyl, anthanthrenyl, truxenyl.

3. The 9,10-dihydro-acridine derivative according to claim 1, wherein R.sub.5 are each independently selected from phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, pyrenyl, perylenyl, corranulenyl, triphenylene, fluoranthenyl.

4. The 9,10-dihydro-acridine derivative according to claim 2, wherein R.sub.5 are each independently selected from biphenylyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, pyrenyl, perylenyl, corranulenyl, triphenylene, or fluoranthenyl.

5. The 9,10-dihydro-acridine derivative according to claim 1, having any of the following molecular structures: ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222## ##STR00223## ##STR00224## ##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232## ##STR00233## ##STR00234##

6. The 9,10-dihydro-acridine derivative according to claim 1, wherein the 9,10-dihydro-acridine derivative is a hole transport material.

7. A method for preparing the 9,10-dihydro-acridine derivative according to claim 1, wherein the compound of Formula (I) is synthesized through the following steps: subjecting a compound of Formula (A) and a compound of Formula (B) as starting materials to a nucleophilic addition reaction, to obtain an intermediate 1; subjecting the intermediate 1 and a compound of Formula (D) to a dehydration-condensation reaction in the presence of Eaton's Reagent, to obtain an intermediate 2; and subjecting the intermediate 2 and a compound of Formula (E) to a coupling reaction in the presence of a catalyst, to obtain the compound of Formula (I); where the synthesis route for the compound of Formula (I) is shown below: ##STR00235## or subjecting the compound of Formula (A) and the compound of Formula (F) as starting materials to a nucleophilic addition reaction, to obtain an intermediate 3; subjecting the intermediate 3 to a nucleophilic substitution reaction, to obtain an intermediate 3′; subjecting the intermediate 3′ and a compound of Formula (G) to a Suzuki reaction, to obtain an intermediate 4; and subjecting the intermediate 4 and the compound of Formula (E) to a coupling reaction in the presence of a catalyst, to obtain the compound of Formula (I); where the synthesis route for the compound of Formula (I) is shown below: ##STR00236## in which W is selected from hydrogen, fluoro, chloro, bromo or iodo, and -OTf is triflate.

8. An organic light-emitting device, having at least one functional layer containing a 9,10-dihydro-acridine derivative, having a structure of Formula (I): ##STR00237## wherein T is selected from O, S, C(R.sub.3)(R.sub.4) or N(R.sub.5); R.sub.1-R.sub.4 and R.sub.6-R.sub.7 are each independently selected from hydrogen; R.sub.5 is a C.sub.6-C.sub.60 substituted or unsubstituted aryl group; Ar.sub.1 is a C.sub.6-C.sub.60 substituted or unsubstituted aryl group; p is an integer from 1 to 5, q.sub.2 is an integer from 1 to 4, and q.sub.3 is an integer from 1 to 4; Ar.sub.3 and Ar.sub.4 are each independently selected from the following groups that are unsubstituted or substituted with 1-4 R.sub.1a: phenyl, biphenylyl, terphenylyl, fluorenyl; in which R.sub.1a is a C.sub.1-C.sub.6 alkyl group.

9. The organic light-emitting device according to claim 8, wherein the functional layer is a hole transport layer and/or an electron blocking layer.

10. The organic light-emitting device according to claim 8, wherein the functional layer is a light emitting layer.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) In order to more clearly explain the technical solutions in the specific embodiments of the present invention or in the prior art, the drawings used in the description of the specific embodiments or the prior art will be briefly described below. Obviously, the drawings depicted below are merely some embodiments of the present invention, and those skilled in the art can obtain other drawings based on these drawings without any creative efforts.

(2) FIG. 1 is a schematic structural view of an organic light-emitting device according to Examples 74 to 83 and Comparative Example 1 of the present invention.

(3) FIG. 2 compares the theoretical calculation results of the HOMO levels, the LUMO levels, and the single-triplet potential difference ΔEst of the compound of Formula C-2 provided in Example 2 of the present invention and the compound NPB provided in Comparative Example 1; and

(4) FIG. 3 compares the theoretical calculation results of the HOMO levels, the LUMO levels, and the single-triplet potential difference ΔEst of the compounds C-61, C-109 and C-12 provided in the present invention.

LIST OF REFERENCE NUMERALS

(5) 1-anode, 2-hole injection layer, 3-hole transport layer, 4-light emitting layer, 5-electron transport layer, 6-electron injection layer, 7-cathode.

DETAILED DESCRIPTION

(6) The technical solutions of the present invention will be described clearly and fully with reference to the accompanying drawings. Apparently, the embodiments described are some preferred embodiments, rather than all of the embodiments of the present invention. All other embodiments obtained by a person of ordinary skill in the art without creative efforts based on the embodiments of the present invention shall fall within the protection scope of the present invention.

(7) It is to be understood that in the description of the present invention, the terms “first” and “second” are used herein for purposes of description, and are not intended to indicate or imply relative importance.

(8) The present invention can be embodied in many different forms and is not limited to the embodiments described herein. Conversely, these embodiments are provided for the purpose of making the disclosure of the present invention more thorough and comprehensive and conveying the concept of the present invention fully to those skilled in the art, and the scope of the present invention is defined merely by the claims. In the figures, for the sake of clarity, the dimensions and relative dimensions of the layers and regions will be exaggerated. It should be understood that when an element, for example, a layer, is referred to as being “formed” or “disposed” “on” another element, the element may be directly disposed on the other element or an intervening element may be present. Conversely, when an element is referred to as being “directly formed on” or “directly disposed on” another element, no intervening element is present.

Example 1

(9) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-1:

(10) ##STR00053##

(11) The synthesis route for the 9,10-dihydro-acridine derivative of Formula C-1 is shown below:

(12) ##STR00054##

(13) The method for preparing the 9,10-dihydro-acridine derivative of Formula C-1 comprises specifically the following steps.

(14) (1) Synthesis of Intermediate 1-1

(15) Under nitrogen atmosphere, 9(10H)-acridone (the compound of Formula A-1) (19.5 g, 100 mmol), and tetrahydrofuran (700 mL) were added to a 1 L three-neck flask. A phenyl magnesium bromide (the compound of Formula B-1) solution (110 mL, 1 M) was added at −20° C., reacted at room temperature for 8 hrs, and then quenched by adding an aqueous ammonium chloride solution. The reaction solution was extracted with dichloromethane (3×), and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the intermediate 1-1 as a solid (24 g, yield: 88%).

(16) (2) Synthesis of Intermediate 2-1

(17) Under nitrogen atmosphere, the intermediate 1-1 (22.0 g, 80 mmol), dibenzofuran (the compound of Formula D-1) (27 g, 160 mmol), and dichloromethane (600 mL) were added to a 1 L three-neck flask. Eaton's Reagent (1.8 mL, 0.9 M) was added dropwise, reacted at room temperature for 30 min, and then quenched by adding a sodium bicarbonate solution. The reaction solution was extracted with toluene (3×), and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the intermediate 2-1 as a solid (13.5 g, yield 40%).

(18) (3) Synthesis of 9,10-dihydro-acridine derivative C-1

(19) Under nitrogen atmosphere, the intermediate 2-1 (8 g, 20 mmol), palladium diacetate (0.13 g, 0.6 mmol), tri-tert-butylphosphine (0.45 g, 2.2 mmol), a compound of Formula E-1 (6.0 g, 22 mmol), sodium-t-butoxide (5.7 g), and toluene (300 mL) were added, reacted at 110° C. for 12 hrs, and then cooled to room temperature. The reaction solution was extracted with chloroform, and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the compound C-1 as a solid (10.0 g, yield 82%).

(20) Element analysis: (C46H33NO) calculated: C, 89.73; H, 5.40; N, 2.27; O, 2.60; found: C, 89.71; H, 5.45; N, 2.28; O, 2.57, HRMS (ESI) m/z (M+): calculated: 615.2562; found: 615.2571.

Example 2

(21) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-2:

(22) ##STR00055##

(23) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-2 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-1 provided in Example 1, except that:

(24) the compound E-1 in Step (3) of Example 1 was replaced by the compound of Formula E-2, and the yield was 80%:

(25) ##STR00056##

Example 3

(26) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-3:

(27) ##STR00057##

(28) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-3 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-1 provided in Example 1, except that:

(29) the compound E-1 in Step (3) of Example 1 was replaced by the compound of Formula E-3, and the yield was 78%:

(30) ##STR00058##

Example 4

(31) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-4:

(32) ##STR00059##

(33) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-4 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-1 provided in Example 1, except that:

(34) the compound E-1 in Step (3) of Example 1 was replaced by the compound of Formula E-4, and the yield was 85%:

(35) ##STR00060##

Example 5

(36) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-5:

(37) ##STR00061##

(38) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-5 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-1 provided in Example 1, except that:

(39) the compound E-1 in Step (3) of Example 1 was replaced by the compound of Formula E-5, and the yield was 84%:

(40) ##STR00062##

Example 6

(41) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-6:

(42) ##STR00063##

(43) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-6 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-1 provided in Example 1, except that:

(44) the compound E-1 in Step (3) of Example 1 was replaced by the compound of Formula E-6, and the yield was 84%:

(45) ##STR00064##

Example 7

(46) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-7:

(47) ##STR00065##

(48) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-7 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-1 provided in Example 1, except that:

(49) the compound E-1 in Step (3) of Example 1 was replaced by the compound of Formula E-7. The yield was 83%:

(50) ##STR00066##

Example 8

(51) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-8:

(52) ##STR00067##

(53) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-8 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-1 provided in Example 1, except that:

(54) the compound E-1 in Step (3) of Example 1 was replaced by the compound of Formula E-8. The yield was 84%:

(55) ##STR00068##

Example 9

(56) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-9:

(57) ##STR00069##

(58) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-9 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-1 provided in Example 1, except that:

(59) the compound E-1 in Step (3) of Example 1 was replaced by the compound of Formula E-9. The yield was 85%:

(60) ##STR00070##

Example 10

(61) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-10:

(62) ##STR00071##

(63) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-10 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-1 provided in Example 1, except that:

(64) the compound E-1 in Step (3) of Example 1 was replaced by the compound of Formula E-10. The yield was 84%:

(65) ##STR00072##

Example 11

(66) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-11:

(67) ##STR00073##

(68) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-11 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-1 provided in Example 1, except that:

(69) the compound E-1 in Step (3) of Example 1 was replaced by the compound of Formula E-11. The yield was 83%:

(70) ##STR00074##

Example 12

(71) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-12:

(72) ##STR00075##

(73) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-12 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-1 provided in Example 1, except that:

(74) the compound E-1 in Step (3) of Example 1 was replaced by the compound of Formula E-12. The yield was 85%:

(75) ##STR00076##

Example 13

(76) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-13:

(77) ##STR00077##

(78) The synthesis route for the 9,10-dihydro-acridine derivative of Formula C-13 is shown below:

(79) ##STR00078##

(80) The method for preparing the 9,10-dihydro-acridine derivative of Formula C-13 comprises specifically the following steps.

(81) (1) Synthesis of Intermediate 1-1

(82) Under nitrogen atmosphere, 9(10H)-acridone (the compound of Formula A-1) (19.5 g, 100 mmol), and tetrahydrofuran (700 mL) were added to a 1 L three-neck flask. A phenyl magnesium bromide (the compound of Formula B-1) solution (110 mL, 1 M) was added at −20° C., reacted at room temperature for 8 hrs, and then quenched by adding an aqueous ammonium chloride solution. The reaction solution was extracted with dichloromethane (3×), and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the intermediate 1-1 as a solid (24 g, yield: 88%).

(83) (2) Synthesis of Intermediate 2-2

(84) Under nitrogen atmosphere, the intermediate 1-1 (22.0 g, 80 mmol), dibenzothiophene (the compound of Formula D-2) (29 g, 160 mmol), and dichloromethane (600 mL) were added to a 1 L three-neck flask. Eaton's Reagent (1.8 mL, 0.9 M) was added dropwise, reacted at room temperature for 30 min, and then quenched by adding a sodium bicarbonate solution. The reaction solution was extracted with toluene (3×), and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the intermediate 2-2 as a solid (13.3 g, yield 38%).

(85) (3) Synthesis of 9,10-dihydro-acridine derivative C-13

(86) Under nitrogen atmosphere, the intermediate 2-2 (8.8 g, 20 mmol), palladium diacetate (0.13 g, 0.6 mmol), tri-tert-butylphosphine (0.45 g, 2.2 mmol), a compound of Formula E-1 (6.0 g 22 mmol), sodium-t-butoxide (5.7 g), and toluene (300 mL) were added, reacted at 110° C. for 12 hrs, and then cooled to room temperature. The reaction solution was extracted with chloroform, and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the compound C-13 as a solid (10.7 g, yield 85%).

(87) Element analysis: (C46H33NS) calculated: C, 87.44; H, 5.26; N, 2.22; S, 5.07; found: C, 87.41; H, 5.29; N, 2.20; S, 5.03, HRMS (ESI) m/z (M+): calculated: 631.2334; found: 631.2347.

Example 14

(88) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-14:

(89) ##STR00079##

(90) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-14 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-13 provided in Example 13, except that:

(91) the compound E-1 in Step (3) of Example 13 was replaced by the compound of Formula E-2, and the yield was 82%:

(92) ##STR00080##

Example 15

(93) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-15:

(94) ##STR00081##

(95) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-15 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-13 provided in Example 13, except that:

(96) the compound E-1 in Step (3) of Example 13 was replaced by the compound of Formula E-3, and the yield was 83%:

(97) ##STR00082##

Example 16

(98) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-16:

(99) ##STR00083##

(100) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-16 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-13 provided in Example 13, except that:

(101) the compound E-1 in Step (3) of Example 13 was replaced by the compound of Formula E-4, and the yield was 85%:

(102) ##STR00084##

Example 17

(103) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-17:

(104) ##STR00085##

(105) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-17 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-13 provided in Example 13, except that:

(106) the compound E-1 in Step (3) of Example 13 was replaced by the compound of Formula E-5, and the yield was 87%:

(107) ##STR00086##

Example 18

(108) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-18:

(109) ##STR00087##

(110) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-18 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-13 provided in Example 13, except that:

(111) the compound E-1 in Step (3) of Example 13 was replaced by the compound of Formula E-6, and the yield was 83%:

(112) ##STR00088##

Example 19

(113) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-19:

(114) ##STR00089##

(115) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-19 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-13 provided in Example 13, except that:

(116) the compound E-1 in Step (3) of Example 13 was replaced by the compound of Formula E-7. The yield was 83%:

(117) ##STR00090##

Example 20

(118) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-20:

(119) ##STR00091##

(120) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-20 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-13 provided in Example 13, except that:

(121) the compound E-1 in Step (3) of Example 13 was replaced by the compound of Formula E-8. The yield was 85%:

(122) ##STR00092##

Example 21

(123) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-21:

(124) ##STR00093##

(125) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-21 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-13 provided in Example 13, except that:

(126) the compound E-1 in Step (3) of Example 13 was replaced by the compound of Formula E-9. The yield was 81%:

(127) ##STR00094##

Example 22

(128) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-22:

(129) ##STR00095##

(130) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-22 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-13 provided in Example 13, except that:

(131) the compound E-1 in Step (3) of Example 13 was replaced by the compound of Formula E-10. The yield was 82%:

(132) ##STR00096##

Example 23

(133) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-23:

(134) ##STR00097##

(135) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-23 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-13 provided in Example 13, except that:

(136) the compound E-1 in Step (3) of Example 13 was replaced by the compound of Formula E-11. The yield was 85%:

(137) ##STR00098##

Example 24

(138) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-24:

(139) ##STR00099##

(140) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-24 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-13 provided in Example 13, except that:

(141) the compound E-1 in Step (3) of Example 13 was replaced by the compound of Formula E-12. The yield was 83%:

(142) ##STR00100##

Example 25

(143) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-25:

(144) ##STR00101##

(145) The synthesis route for the 9,10-dihydro-acridine derivative of Formula C-25 is shown below:

(146) ##STR00102##

(147) The method for preparing the 9,10-dihydro-acridine derivative of Formula C-25 comprises specifically the following steps.

(148) (1) Synthesis of Intermediate 1-1

(149) Under nitrogen atmosphere, 9(10H)-acridone (the compound of Formula A-1) (19.5 g, 100 mmol), and tetrahydrofuran (700 mL) were added to a 1 L three-neck flask. A phenyl magnesium bromide (the compound of Formula B-1) solution (110 mL, 1 M) was added at −20° C., reacted at room temperature for 8 hrs, and then quenched by adding an aqueous ammonium chloride solution. The reaction solution was extracted with dichloromethane (3×), and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the intermediate 1-1 as a solid (24 g, yield: 88%).

(150) (2) Synthesis of Intermediate 2-3

(151) Under nitrogen atmosphere, the intermediate 1-1 (22.0 g, 80 mmol), a compound of Formula D-3 (35 g, 160 mmol), and dichloromethane (1000 mL) were added to a 2 L three-neck flask. Eaton's Reagent (1.8 mL, 0.9 M) was added dropwise, reacted at room temperature for 30 min, and then quenched by adding a sodium bicarbonate solution. The reaction solution was extracted with toluene (3×), and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the intermediate 2-3 as a solid (12.8 g, yield 34%).

(152) (3) Synthesis of 9,10-dihydro-acridine derivative C-25

(153) Under nitrogen atmosphere, the intermediate 2-3 (9.5 g, 20 mmol), palladium diacetate (0.13 g, 0.6 mmol), tri-tert-butylphosphine (0.45 g, 2.2 mmol), a compound of Formula E-1 (6.0 g, 22 mmol), sodium-t-butoxide (5.7 g), and toluene (300 mL) were added, reacted at 110° C. for 12 hrs, and then cooled to room temperature. The reaction solution was extracted with chloroform, and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the compound C-25 as a solid (11.3 g, yield 85%).

(154) Element analysis: (C50H35NO) calculated: C, 90.19; H, 5.30; N, 2.10; O, 2.40; found: C, 90.13; H, 5.33; N, 2.15; O, 2.43, HRMS (ESI) m/z (M+): calculated: 665.2719; found: 665.2707.

Example 26

(155) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-26:

(156) ##STR00103##

(157) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-26 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-25 provided in Example 25, except that:

(158) the compound E-1 in Step (3) of Example 25 was replaced by the compound of Formula E-2, and the yield was 81%:

(159) ##STR00104##

Example 27

(160) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-27:

(161) ##STR00105##

(162) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-27 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-25 provided in Example 25, except that:

(163) the compound E-1 in Step (3) of Example 25 was replaced by the compound of Formula E-3, and the yield was 84%:

(164) ##STR00106##

Example 28

(165) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-28:

(166) ##STR00107##

(167) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-28 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-25 provided in Example 25, except that:

(168) the compound E-1 in Step (3) of Example 25 was replaced by the compound of Formula E-4, and the yield was 85%:

(169) ##STR00108##

Example 29

(170) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-29:

(171) ##STR00109##

(172) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-29 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-25 provided in Example 25, except that:

(173) the compound E-1 in Step (3) of Example 25 was replaced by the compound of Formula E-5, and the yield was 86%:

(174) ##STR00110##

Example 30

(175) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-30:

(176) ##STR00111##

(177) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-30 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-25 provided in Example 25, except that:

(178) the compound E-1 in Step (3) of Example 25 was replaced by the compound of Formula E-6, and the yield was 82%:

(179) ##STR00112##

Example 31

(180) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-31:

(181) ##STR00113##

(182) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-31 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-25 provided in Example 25, except that:

(183) the compound E-1 in Step (3) of Example 25 was replaced by the compound of Formula E-7. The yield was 85%:

(184) ##STR00114##

Example 32

(185) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-32:

(186) ##STR00115##

(187) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-32 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-25 provided in Example 25, except that:

(188) the compound E-1 in Step (3) of Example 25 was replaced by the compound of Formula E-8. The yield was 84%:

(189) ##STR00116##

Example 33

(190) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-33:

(191) ##STR00117##

(192) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-33 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-25 provided in Example 25, except that:

(193) the compound E-1 in Step (3) of Example 25 was replaced by the compound of Formula E-9. The yield was 84%:

(194) ##STR00118##

Example 34

(195) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-34:

(196) ##STR00119##

(197) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-34 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-25 provided in Example 25, except that:

(198) the compound E-1 in Step (3) of Example 25 was replaced by the compound of Formula E-10. The yield was 82%:

(199) ##STR00120##

Example 35

(200) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-35:

(201) ##STR00121##

(202) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-35 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-25 provided in Example 25, except that:

(203) the compound E-1 in Step (3) of Example 25 was replaced by the compound of Formula E-11. The yield was 83%:

(204) ##STR00122##

Example 36

(205) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-36:

(206) ##STR00123##

(207) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-36 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-25 provided in Example 25, except that:

(208) the compound E-1 in Step (3) of Example 25 was replaced by the compound of Formula E-12. The yield was 84%:

(209) ##STR00124##

Example 37

(210) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-49:

(211) ##STR00125##

(212) The synthesis route for the 9,10-dihydro-acridine derivative of Formula C-49 is shown below:

(213) ##STR00126##

(214) The method for preparing the 9,10-dihydro-acridine derivative of Formula C-49 comprises specifically the following steps.

(215) (1) Synthesis of Intermediate 5-1

(216) Under nitrogen atmosphere, 9(10H)-acridone (the compound of Formula A-1) (19.5 g, 100 mmol), palladium diacetate (0.65 g, 3 mmol), tri-tert-butylphosphine (2.25 g, 11.0 mmol), the compound of Formula E-1 (30.0 g, 110 mmol), sodium-t-butoxide (28.5 g), and toluene (100 mL) were added, reacted at 110° C. for 12 hrs, and then cooled to room temperature. The reaction solution was extracted with chloroform, and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the intermediate 5-1 as a solid (33.7 g, yield 87%).

(217) (2) Synthesis of Intermediate 6-1

(218) Under nitrogen atmosphere, the intermediate 5-1 (31 g, 80 mmol) and tetrahydrofuran (800 mL) were added. A phenyl magnesium bromide (the compound of Formula B-1) solution (88 mL, 1 M) was added at −20° C., reacted at room temperature for 8 hrs, and then quenched by adding an aqueous ammonium chloride solution. The reaction solution was extracted with dichloromethane (3×), and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the intermediate 6-1 as a solid (29.1 g, yield: 78%).

(219) (3) Synthesis of 9,10-dihydro-acridine derivative C-49

(220) Under nitrogen atmosphere, the intermediate 6-1 (23.5 g, 50 mmol), tetrahydrofuran (1000 mL), triphenylphosphine (19 g, 150 mmol), carbazole (the compound of Formula D-4) (10 g, 60 mmol), and DEAD (diethyl azodiformate) (10.5 g, 60 mmol) were added, and reacted at room temperature for 12 hrs. The reaction solution was extracted with dichloromethane (3×), and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the compound C-49 as a solid (20.1 g, yield: 66%).

(221) Element analysis: (C46H34N2) calculated: C, 89.87; H, 5.57; N, 4.56; found: C, 89.91; H, 5.59; N, 4.51; HRMS (ESI) m/z (M+): calculated: 614.2722; found: 614.2731.

Example 38

(222) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-50:

(223) ##STR00127##

(224) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-50 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-49 provided in Example 37, except that:

(225) the compound E-1 in Step (3) of Example 37 was replaced by the compound of Formula E-2, and the yield was 85%:

(226) ##STR00128##

Example 39

(227) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-51:

(228) ##STR00129##

(229) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-51 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-49 provided in Example 37, except that:

(230) the compound E-1 in Step (3) of Example 37 was replaced by the compound of Formula E-3, and the yield was 78%:

(231) ##STR00130##

Example 40

(232) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-52:

(233) ##STR00131##

(234) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-52 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-49 provided in Example 37, except that:

(235) the compound E-1 in Step (3) of Example 37 was replaced by the compound of Formula E-4, and the yield was 85%:

(236) ##STR00132##

Example 41

(237) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-53:

(238) ##STR00133##

(239) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-53 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-49 provided in Example 37, except that:

(240) the compound E-1 in Step (3) of Example 37 was replaced by the compound of Formula E-5, and the yield was 82%:

(241) ##STR00134##

Example 42

(242) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-54:

(243) ##STR00135##

(244) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-54 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-49 provided in Example 37, except that:

(245) the compound E-1 in Step (3) of Example 37 was replaced by the compound of Formula E-6, and the yield was 84%:

(246) ##STR00136##

Example 43

(247) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-55:

(248) ##STR00137##

(249) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-55 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-49 provided in Example 37, except that:

(250) the compound E-1 in Step (3) of Example 37 was replaced by the compound of Formula E-7. The yield was 81%:

(251) ##STR00138##

Example 44

(252) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-56:

(253) ##STR00139##

(254) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-56 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-49 provided in Example 37, except that:

(255) the compound E-1 in Step (3) of Example 37 was replaced by the compound of Formula E-8. The yield was 84%:

(256) ##STR00140##

Example 45

(257) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-57:

(258) ##STR00141##

(259) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-57 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-49 provided in Example 37, except that:

(260) the compound E-1 in Step (3) of Example 37 was replaced by the compound of Formula E-9. The yield was 85%:

(261) ##STR00142##

Example 46

(262) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-58:

(263) ##STR00143##

(264) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-58 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-49 provided in Example 37, except that:

(265) the compound E-1 in Step (3) of Example 37 was replaced by the compound of Formula E-10. The yield was 82%:

(266) ##STR00144##

Example 47

(267) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-59:

(268) ##STR00145##

(269) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-59 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-49 provided in Example 37, except that:

(270) the compound E-1 in Step (3) of Example 37 was replaced by the compound of Formula E-11. The yield was 83%:

(271) ##STR00146##

Example 48

(272) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-60:

(273) ##STR00147##

(274) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-60 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-49 provided in Example 37, except that:

(275) the compound E-1 in Step (3) of Example 37 was replaced by the compound of Formula E-12. The yield was 85%:

(276) ##STR00148##

Example 49

(277) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-61:

(278) ##STR00149##

(279) The synthesis route for the 9,10-dihydro-acridine derivative of Formula C-61 is shown below:

(280) ##STR00150##

(281) The method for preparing the 9,10-dihydro-acridine derivative of Formula C-61 comprises specifically the following steps.

(282) (1) Synthesis of Intermediate 1-1

(283) Under nitrogen atmosphere, 9(10H)-acridone (the compound of Formula A-1) (19.5 g, 100 mmol), and tetrahydrofuran (700 mL) were added to a 1 L three-neck flask. A phenyl magnesium bromide (the compound of Formula B-1) solution (110 mL, 1 M) was added at −20° C., reacted at room temperature for 8 hrs, and then quenched by adding an aqueous ammonium chloride solution. The reaction solution was extracted with dichloromethane (3×), and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the intermediate 1-1 as a solid (24 g, yield: 88%).

(284) (2) Synthesis of Intermediate 2-4

(285) Under nitrogen atmosphere, the intermediate 1-1 (22.0 g, 80 mmol), 9-phenylcarbazole (the compound of Formula D-5) (20 g, 80 mmol), and dichloromethane (800 mL) were added. Then, a solution of boron trifluoride (11.5 mL, 80 mmol) in diethyl ether was added dropwise, reacted at room temperature for 5 hrs, and then quenched by adding water. The reaction solution was extracted with toluene (3×), and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the intermediate 2-4 as a solid (33.3 g, yield: 85%).

(286) (3) Synthesis of 9,10-dihydro-acridine derivative C-61

(287) Under nitrogen atmosphere, the intermediate 2-4 (10.0 g, 20 mmol), palladium diacetate (0.13 g, 0.6 mmol), tri-tert-butylphosphine (0.45 g, 2.2 mmol), a compound of Formula E-1 (6.0 g, 22 mmol), sodium-t-butoxide (5.7 g), and toluene (300 mL) were added, reacted at 110° C. for 12 hrs, and then cooled to room temperature. The reaction solution was extracted with chloroform, and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the compound C-61 as a solid (11.5 g, yield 84%).

(288) Element analysis: (C52H38N2) calculated: C, 90.40; H, 5.54; N, 4.05; found: C, 90.43; H, 5.51; N, 4.03; HRMS (ESI) m/z (M+): calculated: 690.3035; found: 690.3017.

Example 50

(289) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-62:

(290) ##STR00151##

(291) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-62 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-61 provided in Example 49, except that:

(292) the compound E-1 in Step (3) of Example 49 was replaced by the compound of Formula E-2, and the yield was 82%:

(293) ##STR00152##

Example 51

(294) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-63:

(295) ##STR00153##

(296) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-63 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-63 provided in Example 49, except that:

(297) the compound E-1 in Step (3) of Example 49 was replaced by the compound of Formula E-3, and the yield was 80%:

(298) ##STR00154##

Example 52

(299) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-64:

(300) ##STR00155##

(301) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-64 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-61 provided in Example 49, except that:

(302) the compound E-1 in Step (3) of Example 49 was replaced by the compound of Formula E-4, and the yield was 81%:

(303) ##STR00156##

Example 53

(304) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-65:

(305) ##STR00157##

(306) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-65 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-61 provided in Example 49, except that:

(307) the compound E-1 in Step (3) of Example 49 was replaced by the compound of Formula E-5, and the yield was 85%:

(308) ##STR00158##

Example 54

(309) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-66:

(310) ##STR00159##

(311) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-66 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-61 provided in Example 49, except that:

(312) the compound E-1 in Step (3) of Example 49 was replaced by the compound of Formula E-6, and the yield was 83%:

(313) ##STR00160##

Example 55

(314) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-67:

(315) ##STR00161##

(316) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-67 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-61 provided in Example 49, except that:

(317) the compound E-1 in Step (3) of Example 49 was replaced by the compound of Formula E-7. The yield was 82%:

(318) ##STR00162##

Example 56

(319) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-68:

(320) ##STR00163##

(321) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-68 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-61 provided in Example 49, except that:

(322) the compound E-1 in Step (3) of Example 49 was replaced by the compound of Formula E-8. The yield was 85%:

(323) ##STR00164##

Example 57

(324) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-69:

(325) ##STR00165##

(326) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-69 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-61 provided in Example 49, except that:

(327) the compound E-1 in Step (3) of Example 49 was replaced by the compound of Formula E-9. The yield was 83%:

(328) ##STR00166##

Example 58

(329) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-70:

(330) ##STR00167##

(331) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-70 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-61 provided in Example 49, except that:

(332) the compound E-1 in Step (3) of Example 49 was replaced by the compound of Formula E-10. The yield was 86%:

(333) ##STR00168##

Example 59

(334) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-71:

(335) ##STR00169##

(336) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-71 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-61 provided in Example 49, except that:

(337) the compound E-1 in Step (3) of Example 49 was replaced by the compound of Formula E-11. The yield was 82%:

(338) ##STR00170##

Example 60

(339) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-72:

(340) ##STR00171##

(341) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-72 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-61 provided in Example 49, except that:

(342) the compound E-1 in Step (3) of Example 49 was replaced by the compound of Formula E-12. The yield was 81%:

(343) ##STR00172##

Example 61

(344) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-74:

(345) ##STR00173##

(346) The synthesis route for the 9,10-dihydro-acridine derivative of Formula C-74 is shown below:

(347) ##STR00174##

(348) The method for preparing the 9,10-dihydro-acridine derivative of Formula C-74 comprises specifically the following steps.

(349) (1) Synthesis of Intermediate 3-1

(350) Under nitrogen atmosphere, the compound of Formula F-1 (24.6 g, 100 mmol), and tetrahydrofuran (500 mL) were added. At −78° C., n-butyl lithium (63 mL, 1.6 M) was added dropwise, reacted for 30 min at a low temperate and then for 3 hrs at an elevated temperature of 30° C., and then cooled to −78° C. A solution of 9(10H)-acridone (the compound of Formula A-1) (500 mL, 0.2 M, 9.5 g (100 mmol)) was added, slowly heated to 30° C., reacted for 15 hrs, and then quenched by adding an aqueous ammonium chloride solution. The reaction solution was extracted with chloroform, and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the intermediate 3-1 as a solid (20.3 g, yield 56%);

(351) (2) Synthesis of Intermediate 3-1′

(352) Under nitrogen atmosphere, the intermediate 3-1 (14.5 g, 40 mmol), triethylamine (5.0 g, 48 mmol), and dichloromethane (400 mL) were added. Trifluoromethanesulfonic anhydride (13.5 g, 48 mmol) was added at −20° C., and reacted at room temperature for 3 hrs. The reaction solution was extracted with toluene (3×), and then the solvent was removed by rotary evaporation. The residue was washed with methanol (3×), to obtain an intermediate 3-1′ (17 g, yield: 87%).

(353) (3) Synthesis of Intermediate 4-1

(354) Under nitrogen atmosphere, the intermediate 3-1′ (14.8 g, 30 mmol), phenylboronic acid (the compound of Formula G-1) (3.7 g, 30 mmol), potassium phosphate (70 g, 33 mmol), tetrakis(triphenylphosphine) palladium (1.7 g, 1.5 mmol), water (50 mL), and 1,4-dioxane (300 mL) were added, reacted at 120° C. for 8 hrs, and then cooled to room temperature. The reaction solution was extracted with chloroform, and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the intermediate 4-1 as a solid (10.3 g, yield 81%).

(355) (4) Synthesis of 9,10-dihydro-acridine derivative C-74

(356) Under nitrogen atmosphere, the intermediate 4-1 (8.5 g, 20 mmol), palladium diacetate (0.13 g, 0.6 mmol), tri-tert-butylphosphine (0.45 g, 2.2 mmol), the compound of Formula E-1 (6.0 g, 22 mmol), sodium-t-butoxide (5.7 g), and toluene (300 mL) were added, reacted at 110° C. for 12 hrs, and then cooled to room temperature. The reaction solution was extracted with chloroform, and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the compound C-74 as a solid (10.3 g, yield 84%).

(357) Element analysis: (C46H33NO) calculated: C, 89.73; H, 5.40; N, 2.27; O, 2.60; found: C, 89.79; H, 5.37; N, 2.30; O, 2.57; HRMS (ESI) m/z (M+): calculated: 615.2562; found: 615.2577.

Example 62

(358) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-73:

(359) ##STR00175##

(360) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-73 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-74 provided in Example 61, except that:

(361) the compound E-1 in Step (4) of Example 61 was replaced by the compound of Formula E-4, and the yield was 81%:

(362) ##STR00176##

Example 63

(363) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-75:

(364) ##STR00177##

(365) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-75 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-74 provided in Example 61, except that:

(366) the compound E-1 in Step (4) of Example 61 was replaced by the compound of Formula E-11. The yield was 82%:

(367) ##STR00178##

Example 64

(368) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-76:

(369) ##STR00179##

(370) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-76 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-74 provided in Example 61, except that:

(371) the compound E-1 in Step (4) of Example 61 was replaced by the compound of Formula E-12. The yield was 84%:

(372) ##STR00180##

Example 65

(373) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-78:

(374) ##STR00181##

(375) The synthesis route for the 9,10-dihydro-acridine derivative of Formula C-78 is shown below:

(376) ##STR00182##

(377) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-78 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-74 provided in Example 61, except that: the compound F-1 in Step (1) of Example 61 was replaced by the compound of Formula F-2.

(378) Element analysis: (C46H33NS) calculated: C, 87.44; H, 5.26; N, 2.22; S, 5.07; found: C, 87.39; H, 5.24; N, 2.27; S, 5.11; HRMS (ESI) m/z (M+): calculated: 631.2334; found: 631.2316.

Example 66

(379) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-77:

(380) ##STR00183##

(381) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-77 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-78 provided in Example 65, except that:

(382) the compound E-1 in Example 65 was replaced by the compound of Formula E-4, and the yield was 85%:

(383) ##STR00184##

Example 67

(384) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-79:

(385) ##STR00185##

(386) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-79 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-78 provided in Example 65, except that:

(387) the compound E-1 in Example 65 was replaced by the compound of Formula E-11. The yield was 82%:

(388) ##STR00186##

Example 68

(389) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-80:

(390) ##STR00187##

(391) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-80 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-78 provided in Example 65, except that:

(392) the compound E-1 in Example 65 was replaced by the compound of Formula E-12. The yield was 83%:

(393) ##STR00188##

Example 69

(394) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-82:

(395) ##STR00189##

(396) The synthesis route for the 9,10-dihydro-acridine derivative of Formula C-82 is shown below:

(397) ##STR00190##

(398) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-82 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-74 provided in Example 61, except that: the compound F-1 in Step (1) of Example 61 was replaced by the compound of Formula F-3.

(399) Element analysis: (C49H39N) calculated: C, 91.69; H, 6.12; N, 2.18; found: C, 91.63; H, 6.15; N, 2.17; HRMS (ESI) m/z (M+): calculated: 641.3083; found: 641.3095.

Example 70

(400) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-81:

(401) ##STR00191##

(402) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-81 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-82 provided in Example 69, except that:

(403) the compound E-1 in Example 69 was replaced by the compound of Formula E-4, and the yield was 81%:

(404) ##STR00192##

Example 71

(405) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-83:

(406) ##STR00193##

(407) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-83 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-82 provided in Example 69, except that:

(408) the compound E-1 in Example 69 was replaced by the compound of Formula E-11. The yield was 82%:

(409) ##STR00194##

Example 72

(410) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-84:

(411) ##STR00195##

(412) The preparation steps of the 9,10-dihydro-acridine derivative of Formula C-84 were the same as those for the 9,10-dihydro-acridine derivative of Formula C-82 provided in Example 69, except that:

(413) the compound E-1 in Example 69 was replaced by the compound of Formula E-12. The yield was 78%:

(414) ##STR00196##

Example 73

(415) This example provides a 9,10-dihydro-acridine derivative having a structure of Formula C-89:

(416) ##STR00197##

(417) The synthesis route for the 9,10-dihydro-acridine derivative of Formula C-89 is shown below:

(418) ##STR00198##

(419) The method for preparing the 9,10-dihydro-acridine derivative of Formula C-89 comprises specifically the following steps.

(420) (1) Synthesis of Intermediate 3-4

(421) Under nitrogen atmosphere, the compound of Formula F-1 (16.8 g, 100 mmol), and tetrahydrofuran (500 mL) were added. At −78° C., n-butyl lithium (63 mL, 1.6 M) was added dropwise, reacted for 30 min at a low temperate and then for 3 hrs at an elevated temperature of 30° C., and then cooled to −78° C. A solution of 9(10H)-acridone (the compound of Formula A-1) (500 mL, 0.2 M, 9.5 g (100 mmol)) was added, slowly heated to 30° C., reacted for 15 hrs, and then quenched by adding an aqueous ammonium chloride solution. The reaction solution was extracted with chloroform, and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the intermediate 3-4 as a solid (17.3 g, yield 47%);

(422) (2) Synthesis of Intermediate 3-4′

(423) Under nitrogen atmosphere, the intermediate 3-4 (14.5 g, 40 mmol), triethylamine (5.0 g, 48 mmol), and dichloromethane (400 mL) were added. Trifluoromethanesulfonic anhydride (13.5 g, 48 mmol) was added at −20° C., and reacted at room temperature for 3 hrs. The reaction solution was extracted with toluene (3×), and then the solvent was removed by rotary evaporation. The residue was washed with methanol (3×), to obtain an intermediate 3-4′ (17 g, yield: 87%).

(424) (3) Synthesis of Intermediate 4-4

(425) Under nitrogen atmosphere, the intermediate 3-4′ (14.8 g, 30 mmol), the compound of Formula G-2 (5.2 g, 30 mmol), potassium phosphate (70 g, 33 mmol), tetrakis(triphenylphosphine) palladium (1.7 g, 1.5 mmol), water (50 mL), and 1,4-dioxane (300 mL) were added, reacted at 120° C. for 8 hrs, and then cooled to room temperature. The reaction solution was extracted with chloroform, and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the intermediate 4-4 as a solid (11.1 g, yield 77%).

(426) (4) Synthesis of 9,10-dihydro-acridine derivative C-89

(427) Under nitrogen atmosphere, the intermediate 4-4 (9.5 g, 20 mmol), palladium diacetate (0.13 g, 0.6 mmol), tri-tert-butylphosphine (0.45 g, 2.2 mmol), the compound of Formula E-13 (7.1 g, 22 mmol), sodium-t-butoxide (5.7 g), and toluene (300 mL) were added, reacted at 110° C. for 12 hrs, and then cooled to room temperature. The reaction solution was extracted with chloroform, and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel, to obtain the compound C-89 as a solid (12.5 g, yield 87%).

(428) Element analysis: (C53H36N2O) calculated: C, 88.80; H, 5.06; N, 3.91; O, 2.23; found: C, 88.77; H, 5.09; N, 3.87; O, 2.24; HRMS (ESI) m/z (M+): calculated: 716.2828; found: 716.2831.

Example 74

(429) This example provides an organic light-emitting device, which includes, from bottom to top, an anode 1, a hole injection layer 1, a hole transport layer 3, a light emitting layer 4, an electron transport layer 5, an electron injection layer 6 and a cathode 7 stacked in sequence. As shown in FIG. 2.

(430) In the organic light-emitting device, the material of the anode is ITO; and the material of the cathode 7 is the metal Al.

(431) The material of the hole injection layer 2 is HAT(CN)6, having a chemical structure as shown below:

(432) ##STR00199##

(433) The material of the hole injection layer 2 is the 9,10-dihydro-acridine derivative of Formula C-2:

(434) ##STR00200##

(435) The light emitting layer 4 is formed by blending the host material RH and the guest material RD, where the weight ratio of the host material RH and the guest material RD blended is 100:5:

(436) ##STR00201##

(437) The material of the electron transport layer 5 is a compound having a structure below:

(438) ##STR00202##

(439) The material of the electron injection layer 6 is formed by a compound having a structure below, blended with the electron injection material LiF:

(440) ##STR00203##

(441) The organic light-emitting device is configured to have a particular structure of ITO/hole injection layer (HIL)/hole transport layer (HTL, the compound of Formula C-2)/organic light emitting layer (in which the weight ratio of RH:RD is 100:5)/electron transport layer (ETL)/electron injection layer (EIL/LiF)/cathode (Al).

(442) In the organic light-emitting device, since the material of the hole transport layer is the 9,10-dihydro-acridine derivative of Formula C-2, the energy level of the 9,10-dihydro-acridine derivative of Formula C-2 is compared with that of NPB, as shown in FIG. 2.

(443) ##STR00204##
in the compound of Formula C-2 is a group having strong electron donating performance, and the nitrogen atom in the dihydro-acridinyl group forms an aminium radical under the action of an electric field, thus creating a good hole mobility, and ensuring the effective transport of holes in the transport layer. Moreover, in the compound of Formula C-2, a carbazolyl group substituted with phenyl is introduced at the position of Ar.sub.2, so the hole transport performance is further improved by taking advantage of the electron donating performance of the carbazolyl group. The 9,10-dihydro-acridine derivative of Formula C-2, has suitable HOMO level, and can reduce the potential barrier needed to overcome when holes are injected from the anode to the light emitting layer and thus increase the effective injection of holes, thereby reducing the operating voltage of the device and improving the luminescence efficiency of the device.

(444) In the structure of Formula C-2, the dihydro-acridinyl group having a high triplet energy level is linked to a dibenzofuryl group via a σ bond, such that the structure of Formula C-2 has improved triplet energy level. The introduction of modifying groups via a a bond allows the adjustment of the triplet energy level (T.sub.1) of the 9,10-dihydro-acridine derivative of Formula C-2. The high triplet energy level of the 9,10-dihydro-acridine derivative of Formula C-2 facilitates the confining of excitons formed by recombination of electrons and holes in a light emitting region of the light emitting layer of an OLED device, so as to avoid the returning of energy from the light emitting layer to the adjacent hole transport layer. Furthermore, the 9,10-dihydro-acridine derivative of such a connection mode has an elevated LUMO level, which increases the blocking effect for electrons, and makes the electrons retained in the light emitting layer effectively, thereby increasing the probability of recombination of electrons and holes, and improving the luminescence efficiency of the device.

(445) The 9,10-dihydro-acridine derivative of Formula C-2 has high glass transition temperature, good thermal stability and morphological stability, and excellent film-forming performance, and is not amenable to crystallization during the film formation process or during the operation of the OLED device due to heat generation after film formation, thus improving the performance and service life of the device.

(446) In an alternative embodiment, the guest luminescent material in the light emitting layer may also be any 9,10-dihydro-acridine derivative of Formulas (C-1) and (C-3)-(C-109).

(447) In an alternative embodiment, the guest luminescent material in the light emitting layer may also be any other compounds having a chemical structure of general Formula (I).

Example 75

(448) This example provides an organic light-emitting device, which is different from the organic light-emitting device provided in Example 74 in that the material of the hole transport layer is a 9,10-dihydro-acridine derivative having a structure below:

(449) ##STR00205##

Example 76

(450) This example provides an organic light-emitting device, which is different from the organic light-emitting device provided in Example 74 in that the material of the hole transport layer is a 9,10-dihydro-acridine derivative having a structure below:

(451) ##STR00206##

Example 77

(452) This example provides an organic light-emitting device, which is different from the organic light-emitting device provided in Example 74 in that the material of the hole transport layer is a 9,10-dihydro-acridine derivative having a structure below:

(453) ##STR00207##

Example 78

(454) This example provides an organic light-emitting device, which is different from the organic light-emitting device provided in Example 74 in that the material of the hole transport layer is a 9,10-dihydro-acridine derivative having a structure below:

(455) ##STR00208##

Example 79

(456) This example provides an organic light-emitting device, which is different from the organic light-emitting device provided in Example 74 in that the material of the hole transport layer is a 9,10-dihydro-acridine derivative having a structure below:

(457) ##STR00209##

Example 80

(458) This example provides an organic light-emitting device, which is different from the organic light-emitting device provided in Example 74 in that the material of the hole transport layer is a 9,10-dihydro-acridine derivative having a structure below:

(459) ##STR00210##

Example 81

(460) This example provides an organic light-emitting device, which is different from the organic light-emitting device provided in Example 74 in that the material of the hole transport layer is a 9,10-dihydro-acridine derivative having a structure below:

(461) ##STR00211##

Example 82

(462) This example provides an organic light-emitting device, which is different from the organic light-emitting device provided in Example 74 in that the material of the hole transport layer is a 9,10-dihydro-acridine derivative having a structure below:

(463) ##STR00212##

Example 83

(464) This example provides an organic light-emitting device, which is different from the organic light-emitting device provided in Example 74 in that the material of the hole transport layer is a 9,10-dihydro-acridine derivative having a structure below:

(465) ##STR00213##

Comparative Example 1

(466) This comparative example provides an organic light-emitting device, which is different from the organic light-emitting device provided in Example 74 in that the material of the hole transport layer is the compound NPB:

(467) ##STR00214##

Test Example 1

(468) 1. Determination of Glass Transition Temperature

(469) The glass transition temperature of the material according to the present invention was tested by differential scanning calorimetery (DSC) in a range from room temperature to 400° C. at a ramping rate of 10° C./min under nitrogen atmosphere.

(470) 2. The fluorescence and phosphorescence spectra of a solution of the 9,10-dihydro-acridine derivative in toluene (having a concentration of 10.sup.−5 mol/L) were measured at 298 K and 77 K, respectively, the corresponding triplet energy level (T.sub.1) was calculated according to the formula E=1240/λ.

(471) 3. The HOMO level of the material according to the present invention was tested by cyclic voltammetry (CV) using an electrochemical workstation with platinum (Pt) as a counter electrode and silver/silver chloride (Ag/AgCl) as a reference electrode. Under a nitrogen atmosphere, the test was carried out at a scan rate of 100 mV/s in an electrolyte solution containing 0.1 M tetrabutylammonium hexafluorophosphate in dichloromethane, and the potential was calibrated by ferrocene, in which the potential of ferrocene was set to an absolute energy level under vacuum of −4.8 eV:
HOMO=−[E.sub.onset.sup.ox−E.sub.Fc/Fc++4.8] eV

(472) 4. The LUMO level of the material molecule is calculated using the bandgap and HOMO of the material:

(473) HOMO=[LUMO−E.sub.g.sup.opt]eV where the bandgap

(474) $E_g^{\mathrm{opt}}=\frac{1240}{{\lambda }_{\mathrm{onset}}}\mathrm{eV}$
is the initial spectral absorption of the material.

(475) TABLE-US-00001 TABLE 1 9,10-dihydro-acridine C-2 C-4 C-8 C-12 C-16 C-56 C-61 C-68 C-95 C-97 derivative Glass Transition 167 165 171 175 167 173 168 181 167 170 Temperature (° C.) HOMO (eV) −5.30 −5.38 −5.35 −5.36 −5.40 −5.37 −5.31 −5.38 −5.40 −5.37 LUMO (eV) −2.21 2.19 2.32 2.33 2.21 2.17 2.20 2.37 2.20 2.19 T.sub.1 (eV) 3.21 2.87 2.72 2.71 2.82 3.32 3.14 2.67 2.93 2.92

Test Example 2

(476) The current, voltage, brightness, and luminescence spectrum of the device were tested synchronously using PR 650 scanning spectroradiometer and Keithley K 2400 digital source meter. The organic light-emitting devices provided in Examples 67-77 and the comparative example were tested. The results are shown in Table 2.

(477) TABLE-US-00002 TABLE 2 Current Current Material of hole density/mA/ efficiency Chromaticity transport layer Voltage/V cm.sup.2 cd/A (CIE-X, Y) Comparative NPB 5.1 10 21 (0.66, 0.33) Example 1 Example 74 Compound of C-2 4.8 10 23 (0.66, 0.33) Example 75 Compound of C-4 4.7 10 26 (0.66, 0.33) Example 76 Compound of C-8 4.6 10 25 (0.66, 0.33) Example 77 Compound of C-12 4.6 10 26 (0.66, 0.33) Example 78 Compound of C-16 4.7 10 25 (0.66, 0.33) Example 79 Compound of C-56 4.8 10 25 (0.66, 0.33) Example 80 Compound of C-61 4.9 10 24 (0.66, 0.33) Example 81 Compound of C-68 4.2 10 27 (0.66, 0.33) Example 82 Compound of C-95 4.6 10 26 (0.66, 0.33) Example 83 Compound of C-97 4.5 10 25 (0.66, 0.33)

(478) The organic light-emitting devices provided in Examples 74-83 and Comparative Example 1 were tested. The results are shown in Table 2. Compared with the device provided in Comparative Example 1, the OLED devices provided in Examples 74-83 has lowered operating voltage and increased current efficiency, indicating that the 9,10-dihydro-acridine derivative provided in the present invention, when used as a hole transport material in an OLED device, can greatly improve the luminescence efficiency, reduce the driving voltage, and increase the performance of the OLED device.

(479) Apparently, the above-described embodiments are merely examples provided for clarity of description, and are not intended to limit the implementations of the present invention. Other variations or changes can be made by those skilled in the art based on the above description. The embodiments are not exhaustive herein. Obvious variations or changes derived therefrom also fall within the protection scope of the present invention.