Dibenzoheterocyclic compound and preparation method and application thereof

Abstract

A dibenzoheterocyclic compound wherein band gaps of HOMO and LUMO energy levels of the dibenzoheterocyclic compound are wide, light can be emitted in a deep blue light-emitting region; and the LUMO energy level of the dibenzoheterocyclic compound is low, so the LUMO energy level matches with an electron transport layer for electrons injection and transport. The dibenzoheterocyclic compound has hole transport performance, so as a light-emitting layer material, the dibenzoheterocyclic compound balances the ratio of electrons to holes in a light-emitting layer increasing the combination probability and improving the device light-emitting efficiency. The spatial configuration of the dibenzoheterocyclic compound avoids material stacking molecules, reduces annihilation of excitons, and inhibits efficiency roll-off. The dibenzoheterocyclic compound has thermal stability, so deep blue light can be emitted efficiently and stably. With an organic light-emitting diode and a deep blue light-emitting device with high light-emitting efficiency, low working voltage can be obtained.

Claims

1. A dibenzoheterocyclic compound, having a structure as shown in a formula (I): ##STR00049## wherein Ar.sup.1 and Ar.sup.2 are, each independently, selected from unsubstituted C.sub.4-C.sub.60 aryl group; Y.sup.1-Y.sup.8 are, each independently, selected from hydrogen, and cyano group, Y.sup.9-Y.sup.10 are bonded to form a ring B.sup.1, and the ring B.sup.1 is selected from substituted or unsubstituted imidazole ring.

2. The dibenzoheterocyclic compound according to claim 1, having a structure as shown below: ##STR00050##

3. A preparation method of the dibenzoheterocyclic compound according to claim 1, wherein synthesis steps of the dibenzoheterocyclic compound shown in the formula (I) are as follows: taking a compound shown in the formula (A) as a starting material, performing halogenating reaction under the action of a catalyst to obtain an intermediate 1, and enabling the intermediate 1 to react with triphenylphosphine to generate an intermediate 2; enabling the intermediate 2 and a compound shown in the formula (B) to be subjected to Wittig reaction to obtain an intermediate 3; enabling the intermediate 3 and a compound shown in the formula (C) to be subjected to condensation reaction to obtain an intermediate 4; enabling the intermediate 4 to react with a compound of at least one of Y.sup.1-Y.sup.8 to generate an intermediate 4-A; when at least one of Y.sup.9 and Y.sup.10 is not hydrogen, enabling the intermediate 4-A to be subjected to oxidation reaction to obtain an intermediate 5, and enabling the intermediate 5 to react with a cyclic compound forming Y.sup.9 and Y.sup.10 to obtain the dibenzoheterocyclic compound shown in the formula (I); X.sub.1-X.sub.3 are, each independently, selected from halogen; X.sub.4 is oxygen; and R.sub.1-R.sub.8 are, each independently, selected from halogen or hydrogen; a synthesis route of the dibenzoheterocyclic compound shown in the formula (I) is as follows: ##STR00051## ##STR00052##

4. The dibenzoheterocyclic compound according to claim 1, wherein the dibenzoheterocyclic compound is an organic electroluminescent material.

5. An organic light emitting diode, wherein at least one functional layer of the organic light emitting diode contains the dibenzoheterocyclic compound according to claim 1.

6. The organic light emitting diode according to claim 5, wherein the functional layer is a light-emitting layer.

7. The organic light emitting diode according to claim 5, wherein a light-emitting layer material comprises a host material and a guest light-emitting material, and the guest light-emitting material is the dibenzoheterocyclic compound.

8. The organic light emitting diode according to claim 5, wherein a light-emitting layer material comprises a host material and a guest light-emitting dye, and the host material is the dibenzoheterocyclic compound.

9. The organic light emitting diode according to claim 5, wherein the organic light emitting diode is a blue light-emitting device.

10. A display unit, comprising the organic light emitting diode according to claim 5.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) In order to more clearly illustrate the technical schemes in the detailed description of the invention or the prior art, the drawings required in the detailed description of the specific embodiments or the description of the prior art are simply described below. Obviously, the drawings in the following description are some embodiments of the invention, and a person of ordinary skill in the art can also obtain other drawings according to these drawings without any creative work.

(2) FIG. 1 is a structural schematic diagram of an organic light emitting diode according to embodiments 13-17 and a contrast 1 of the invention;

(3) FIG. 2 is a diagram showing theoretical calculation results of the HOMO energy level, the LUMO energy level and E.sub.g of a compound shown in the formula SA-08 provided by an embodiment 6 in the present application;

(4) FIG. 3 is a diagram showing theoretical calculation results of the HOMO level, LUMO level and E.sub.g of the compound shown in the formula SA-34 provided by an embodiment 11 in the present application.

REFERENCE NUMERALS IN THE DRAWINGS

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

DETAILED DESCRIPTION

(6) The technical schemes of the invention will be clearly and completely described below. Obviously, the described embodiments are only a part of the embodiments of the invention but not all of the embodiments. Based on the embodiments in the invention, all other embodiments obtained by a person of ordinary skill in the art without creative work belong to the scope of protection of the invention. In addition, the technical features involved in different embodiments of the invention described below can be combined with one other as long as the technical features do not conflict with one other.

(7) In the description of the invention, it should be noted that the terms “first”, “second” and “third” are used for description only and are not intended to indicate or imply relative importance.

(8) The invention can be implemented in many different forms and should not be construed as being limited to the embodiments stated herein. Instead, by providing these embodiments, the present disclosure is thorough and complete, the concept of the invention is fully delivered to those skilled in the art, and the invention is limited only by the claims. In the drawings, for clarity, the dimensions and relative dimensions of layers and regions are exaggerated. It should be understood that, when a component, such as a layer, is known as “formed on” or “arranged on” another component, this component can be directly arranged on the another component, or an intermediate component can be arranged. On the contrary, when the component is known as “directly formed on” or “directly arranged on” another component, the intermediate component is not arranged.

Embodiment 1

(9) This embodiment provides a synthesis method of an intermediate 4-1, and a synthesis route of the intermediate 4-1 is as shown below:

(10) ##STR00008## ##STR00009##

(11) The synthesis method of the intermediate 4-1 includes the following steps:

(12) 1. Preparation of Intermediate 1-1

(13) In a dry, nitrogen-flushed 2-1 double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, a compound (205.484 g, 1.0 equivalent) shown in the formula A-1, NBS (195.783 g, 1.1 equivalent), AIBN (8.211 g, 0.5 mol percent), and carbon tetrachloride (1 L) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 24 hours. After reaction, water (200 ml) was added to quench the reaction, the reaction solution was extracted, and the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatographic (ethyl acetate/hexane, 1/10) to obtain the intermediate 1-1 (250.260 g, yield: 88%).

(14) 2. Preparation of Intermediate 2-1

(15) In a dry, nitrogen-flushed 2 L double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 1-1 (200.000 g, 1.0 equivalent), triphenylphosphine (193.692 g, 1.05 equivalent), and toluene (1 L) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; and after reaction, the mixture was filtered, and then, the obtained solid was cleaned with hexane (3*800 ml) to obtain a crude product (397.086 g) of the intermediate 2-1.

(16) 3. Preparation of Intermediate 3-1

(17) In a dry, nitrogen-flushed 2-liter double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 2-1 (350.000 g, 1.0 equivalent), potassium tert-butoxide (215.534 g, 3.0 equivalent), and tetrahydrofuran (500 ml) were respectively added firstly, the mixture was stirred for 10 minutes at 0° C., subsequently, 2-bromo-4-chlorobenzaldehyde (a compound shown in the formula B-1) (140.512 g, 1.0 equivalent) dissolved in tetrahydrofuran (300 ml) was added dropwise, and finally, the reaction was stirred for 24 hours at room temperature; after reaction, water (400 ml) was added to quench the reaction. After extraction with ethyl ether (3*1000 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/80) to obtain the intermediate 3-1 (253.062 g, yield: 91%).

(18) 4. Preparation of Intermediate 4-1

(19) In a dry, nitrogen-flushed 2-liter double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 3-1 (203.466 g, 1.0 equivalent) and anhydrous tetrahydrofuran (500 ml) were added, the mixture was stirred for 10 minutes at −78° C., subsequently, 2.5 M butyl lithium dissolved in hexane (430 ml, 2.15 equivalent) was added dropwise and the reaction was stirred for 30 minutes, N,N,N′,N′-tetramethyl-1,2-ethanediamine (170 ml, 2.3 equivalent) was added dropwise and the reaction was stirred for 2 hours, and finally, dichlorodiphenylsilane (the compound shown in the formula C-1) (139.263 g, 1.1 equivalent) was added dropwise; after reaction, a saturated sodium bicarbonate aqueous solution (250 ml) was added to quench the reaction. After extraction with ethyl acetate (3*500 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/35) to obtain the intermediate 4-1 (103.556 g, yield: 84%).

Embodiment 2

(20) This embodiment provides a synthesis method of an intermediate 4-2, and a synthesis route of the intermediate 4-2 is as shown below:

(21) ##STR00010## ##STR00011##

(22) The synthesis method of the intermediate 4-2 includes the following steps:

(23) 1. Preparation of Intermediate 1-2

(24) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, a compound (20.548 g, 1.0 equivalent) shown in the formula A-2, NBS (19.578 g, 1.1 equivalent), AIBN (0.821 g, 0.5 mol percent), and carbon tetrachloride (250 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 24 hours; after reaction, water (200 ml) was added to quench the reaction. After extraction with ethyl acetate (3*200 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/10) to obtain the intermediate 1-2 (16.747 g, yield: 78%).

(25) 2. Preparation of Intermediate 2-2

(26) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 1-2 (20.000 g, 1.0 equivalent), triphenylphosphine (19.369 g, 1.05 equivalent), and toluene (250 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; and after reaction, the mixture was filtered, and then, the obtained solid was cleaned with hexane (3*80 ml) to obtain a crude product (38.231 g) of the intermediate 2-2.

(27) 3. Preparation of Intermediate 3-2

(28) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 2-2 (35.000 g, 1.0 equivalent), potassium tert-butoxide (21.553 g, 3.0 equivalent), and tetrahydrofuran (150 ml) were respectively added the mixture was stirred for 10 minutes at 0° C., subsequently, 2-bromo-6-chlorobenzaldehyde (a compound shown in the formula B-2) (14.051 g, 1.0 equivalent) dissolved in tetrahydrofuran (100 ml) was added dropwise, and finally, the reaction was stirred for 24 hours at room temperature; after reaction, water (50 ml) was added to quench the reaction. After extraction with ethyl ether (3*300 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/75) to obtain the intermediate 3-2 (23.969 g, yield: 92%).

(29) 4. Preparation of Intermediate 4-2

(30) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, firstly the intermediate 3-2 (20.346 g, 1.0 equivalent) and anhydrous tetrahydrofuran (180 ml) were added, the mixture was stirred for 10 minutes at −78° C., subsequently, 2.5 M butyl lithium dissolved in hexane (43 ml, 2.15 equivalent) was added dropwise and the reaction was stirred for 30 minutes, N,N,N′,N′-tetramethyl-1,2-ethanediamine (17 ml, 2.3 equivalent) was added dropwise and the reaction was stirred for 2 hours, and finally, dichlorodiphenylsilane (the compound shown in the formula C-1) (13.926 g, 1.1 equivalent) was added dropwise; after reaction, a saturated sodium bicarbonate aqueous solution (50 ml) was added to quench the reaction. After extraction with ethyl acetate (3*150 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain the intermediate 4-2 (9.616 g, yield: 78%).

Embodiment 3

(31) This embodiment provides a synthesis method of an intermediate 4-3, and a synthesis route of the intermediate 4-3 is as shown below:

(32) ##STR00012## ##STR00013##

(33) The synthesis method of the intermediate 4-3 includes the following steps:

(34) 1. Preparation of Intermediate 1-3

(35) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, a compound (20.548 g, 1.0 equivalent) shown in the formula A-3, NBS (19.578 g, 1.1 equivalent), AIBN (0.821 g, 0.5 mol percent), and carbon tetrachloride (250 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 24 hours; after reaction, water (200 ml) was added to quench the reaction. After extraction with ethyl acetate (3*200 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/10) to obtain the intermediate 1-3 (20.191 g, yield: 71%).

(36) 2. Preparation of Intermediate 2-3

(37) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 1-3 (20.000 g, 1.0 equivalent), triphenylphosphine (19.369 g, 1.05 equivalent), and toluene (250 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; and after reaction, the mixture was filtered, and then, the obtained solid was cleaned with hexane (3*80 ml) to obtain a crude product (38.466 g) of the intermediate 2-3.

(38) 3. Preparation of Intermediate 3-3

(39) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 2-3 (35.000 g, 1.0 equivalent), potassium tert-butoxide (21.553 g, 3.0 equivalent), and tetrahydrofuran (150 ml) were respectively added firstly, the mixture was stirred for 10 minutes at 0° C., subsequently, 2-bromo-5-chlorobenzaldehyde (a compound shown in the formula B-3) (14.051 g, 1.0 equivalent) dissolved in tetrahydrofuran (100 ml) was added dropwise, and finally, the reaction was stirred for 24 hours at room temperature; after reaction, water (50 ml) was added to quench the reaction. After extraction with ethyl ether (3*300 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/70) to obtain the intermediate 3-3 (23.187 g, yield: 89%).

(40) 4. Preparation of Intermediate 4-3

(41) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 3-3 (20.346 g, 1.0 equivalent), and anhydrous tetrahydrofuran (180 ml) were added, the mixture was stirred for 10 minutes at −78° C., subsequently, 2.5 M butyl lithium dissolved in hexane (43 ml, 2.15 equivalent) was added dropwise and the reaction was stirred for 30 minutes, N,N,N′,N′-tetramethyl-1,2-ethanediamine (17 ml, 2.3 equivalent) was added dropwise and the reaction was stirred for 2 hours, and finally, dichlorodiphenylsilane (the compound shown in the formula C-1) (13.926 g, 1.1 equivalent) was added dropwise; after reaction, a saturated sodium bicarbonate aqueous solution (50 ml) was added to quench the reaction. After extraction with ethyl acetate (3*150 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain the intermediate 4-3 (8.383 g, yield: 68%).

Embodiment 4

(42) This embodiment provides a synthesis method of an intermediate 4-4, and a synthesis route of the intermediate 4-4 is as shown below:

(43) ##STR00014## ##STR00015##

(44) The synthesis method of the intermediate 4-4 includes the following steps:

(45) 1. Preparation of Intermediate 1-4

(46) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, firstly a compound (20.548 g, 1.0 equivalent) shown in the formula A-4, NBS (19.578 g, 1.1 equivalent) and AIBN (0.821 g, 0.5 mol percent), then, carbon tetrachloride (250 ml) were respectively added, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 24 hours; after reaction, water (200 ml) was added to quench the reaction. After extraction with ethyl acetate (3*200 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/10) to obtain the intermediate 1-4 (23.867 g, yield: 65%).

(47) 2. Preparation of Intermediate 2-4

(48) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 1-4 (20.000 g, 1.0 equivalent), triphenylphosphine (19.369 g, 1.05 equivalent), and toluene (250 ml) respectively the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; and after reaction, and then, the obtained solid was cleaned with hexane (3*80 ml) to obtain a crude product (37.831 g) of the intermediate 2-4.

(49) 3. Preparation of Intermediate 3-4

(50) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 2-4 (35.000 g, 1.0 equivalent), potassium tert-butoxide (21.553 g, 3.0 equivalent), and tetrahydrofuran (150 ml) were respectively added firstly, the mixture was stirred for 10 minutes at 0° C., subsequently, 2-bromo-3-chlorobenzaldehyde (a compound as shown in the formula B-4) (14.051 g, 1.0 equivalent) dissolved in tetrahydrofuran (100 ml) was added dropwise, and finally, the reaction was stirred for 24 hours at room temperature; after reaction, water (50 ml) was added to quench the reaction. After extraction with ethyl ether (3*300 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/75) to obtain the intermediate 3-4 (22.525 g, yield: 81%).

(51) 4. Preparation of Intermediate 4-4

(52) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 3-4 (20.346 g, 1.0 equivalent) and anhydrous tetrahydrofuran (180 ml) were added, the mixture was stirred for 10 minutes at −78° C., subsequently, 2.5 M butyl lithium dissolved in hexane (43 ml, 2.15 equivalent) was added dropwise and the reaction was stirred for 30 minutes, N,N,N′,N′-tetramethyl-1,2-ethanediamine (17 ml, 2.3 equivalent) was added dropwise and the reaction was stirred for 2 hours, and finally, dichlorodiphenylsilane (the compound shown in the formula C-1) (13.926 g, 1.1 equivalent) was added dropwise; after reaction, a saturated sodium bicarbonate aqueous solution (50 ml) was added to quench the reaction. After extraction with ethyl acetate (3*150 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain the intermediate 4-4 (6.780 g, yield: 47%).

Embodiment 5

(53) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SA-03 below:

(54) ##STR00016##

(55) A synthesis route of the dibenzoheterocyclic compound shown in the formula SA-03 is as shown below:

(56) ##STR00017## ##STR00018##

(57) A preparation method of the dibenzoheterocyclic compound shown in the formula SA-03 includes the following steps:

(58) 1. Preparing an intermediate 4-1 by the synthesis method provided by the embodiment 1

(59) 2. Preparing the dibenzoheterocyclic compound shown in the formula SA-03:

(60) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-1 (5.582 g, 1.0 equivalent), N,N-diphenylamine (a compound as shown in the formula D-1) (4.495 g, 2.05 equivalent), Pd.sub.2(dba).sub.3 (0.275 g, 3 mol percent), potassium tert-butoxide (2.018 g, 2.1 equivalent), and anhydrous toluene (40 ml) were respectively added firstly, the mixture was stirred for 10 minutes, subsequently, tert-butyl phosphate dissolved in toluene (0.03 M, 10 ml) was added, and finally, the mixture was heated refluxly for 6 hours; after reaction, water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain the compound SA-03 (8.312 g, yield: 92%).

(61) Elemental analysis: (C.sub.50H.sub.38N.sub.2Si) theoretical values: C, 86.42; H, 5.51; N, 4.03; measured values: C, 86.39; H, 5.52; N, 4.7; HRMS (ESI) m/z (M.sup.+): theoretical value: 694.2804; measured value: 694.2795.

Embodiment 6

(62) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SA-08 below:

(63) ##STR00019##

(64) A synthesis route of the dibenzoheterocyclic compound shown in the formula SA-08 is as shown below:

(65) ##STR00020## ##STR00021##

(66) A preparation method of the dibenzoheterocyclic compound shown in the formula SA-08 includes the following steps:

(67) 1. Preparing an intermediate 4-1 by the synthesis method provided by the embodiment 1

(68) 2. Preparing the dibenzoheterocyclic compound shown in the formula SA-08:

(69) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-1 (5.582 g, 1.0 equivalent), 4-(N,N-diphenylamino)phenylboric acid (a compound as shown in the formula D-2) (4.904 g, 2.3 equivalent), Pd(PPh.sub.3).sub.4 (0.578 g, 5 mol percent), sodium carbonate (2.649 g, 2.5 equivalent), toluene (40 ml) and water (4 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; after reaction, water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain the compound SA-08 (4.811 g, yield: 62%).

(70) Elemental analysis: (C.sub.44H.sub.40Si) theoretical values: C, 88.54; H, 6.76; measured values: C, 88.50; H, 6.75; HRMS (EI) m/z (M.sup.+): theoretical value: 596.2899; measured value: 596.2903.

Embodiment 7

(71) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SA-11 below:

(72) ##STR00022##

(73) A synthesis route of the dibenzoheterocyclic compound shown in the formula SA-11 is as shown below:

(74) ##STR00023## ##STR00024##

(75) A preparation method of the dibenzoheterocyclic compound shown in the formula SA-11 includes the following steps:

(76) 1. Preparing an intermediate 4-2 by the synthesis method provided by the embodiment 2

(77) 2. Preparing the dibenzoheterocyclic compound shown in the formula SA-11:

(78) (1) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 4-2 (5.582 g, 1.0 equivalent) and anhydrous tetrahydrofuran (180 ml) were added firstly, the mixture was stirred for 10 minutes at −78° C., subsequently, 2.5 M butyl lithium dissolved in hexane (13.0 ml, 2.5 equivalent) was added dropwise and the reaction was stirred for 30 minutes, and N,N-dimethyl formamide (1.0 ml, 2.5 equivalent) was added dropwise and the reaction was stirred for 2 hours; after reaction, a saturated sodium bicarbonate aqueous solution (50 ml) was added to quench the reaction. After extraction with ethyl acetate (3*150 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/25) to obtain an intermediate 4-2-1 (3.899 g, yield: 72%).

(79) (2) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-2-1 (3.332 g, 1.0 equivalent), N-phenyl-o-phenylenediamine (a compound shown in the formula D-3) (3.022 g, 2.05 equivalent), and toluene (50 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 36 hours; after reaction, water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*25 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/15) to obtain the compound SA-11 (5.185 g, yield: 87%).

(80) Elemental analysis: (C.sub.52H.sub.36N.sub.4Si) theoretical values: C, 83.84; H, 4.87; N, 7.52; measured values: C, 83.81; H, 4.85; N, 7.55; HRMS (ESI) m/z (M.sup.+): theoretical value: 744.2709; measured value: 744.2713.

Embodiment 8

(81) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SA-20 below:

(82) ##STR00025##

(83) A synthesis route of the dibenzoheterocyclic compound shown in the formula SA-20 is as follows:

(84) ##STR00026## ##STR00027##

(85) A preparation method of the dibenzoheterocyclic compound shown in the formula SA-20 includes the following steps:

(86) 1. Preparing an intermediate 4-1 by the synthesis method provided by the embodiment 1

(87) 2. Preparing the dibenzoheterocyclic compound having the structure as shown in formula SA-20:

(88) (1) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-1 (5.582 g, 1.0 equivalent), the compound shown in the formula D-4 (5.844 g, 2.05 equivalent), Pd.sub.2(dba).sub.3 (0.275 g, 3 mol percent), potassium tert-butoxide (2.018 g, 2.1 equivalent), and anhydrous toluene (40 ml) were respectively added firstly, the mixture was stirred for 10 minutes, subsequently, tert-butyl phosphate dissolved in toluene (0.03 M, 10 ml) was added, and finally, the mixture was heated refluxly for 6 hours; after reaction, water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain an intermediate 4-1-A.sub.1 (9.716 g, yield: 94%).

(89) (2) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-1-A.sub.1 (5.566 g, 1.0 equivalent), NBS (2.865 g, 2.3 equivalent), AIBN (0.006 g, 0.5 mol percent), and carbon tetrachloride (50 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 24 hours; after reaction, water (20 ml) was added to quench the reaction. After extraction with ethyl acetate (3*25 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain an intermediate 5-1 (5.080 g, yield: 76%).

(90) (3) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 5-1 (4.774 g, 1.0 equivalent), potassium hydroxide (0.842 g, 3.0 equivalent), and 1,2-dimethoxyethane (50 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 4 hours; after reaction, 2,3,4,5-tetraphenylcyclopenta-2,4-dien-1-one (a compound shown in the formula E-1) (3.460 g, 1.8 equivalent), and then, the mixture was heated refluxly for 12 hours; after the temperature returns, water (20 ml) was added to quench the reaction. After extraction with ethyl acetate (3*25 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain the compound SA-20 (2.816 g, total yield: 49%).

(91) Elemental analysis: (C.sub.86H.sub.60N.sub.2Si) theoretical values: C, 89.86; H, 5.26; N, 2.44; measured values: C, 89.89; H, 5.23; N, 2.43; HRMS (ESI) m/z (M.sup.+): theoretical value: 1148.4526; measured value: 1148.4521.

Embodiment 9

(92) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SA-24 below:

(93) ##STR00028##

(94) A synthesis route of the dibenzoheterocyclic compound shown in the formula SA-24 is as shown below:

(95) ##STR00029## ##STR00030## ##STR00031##

(96) A preparation method of the dibenzoheterocyclic compound shown in the formula SA-24 includes the following steps:

(97) 1. Preparing an intermediate 4-1 by the synthesis method provided by the embodiment 1

(98) 2. Preparing the dibenzoheterocyclic compound shown in the formula SA-24:

(99) (1) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-1 (5.582 g, 1.0 equivalent), dibenzofuran-1-boric acid (a compound shown in the formula D-5-1) (2.894 g, 1.05 equivalent), Pd(PPh.sub.3).sub.4 (0.578 g, 5 mol percent), sodium carbonate (2.649 g, 2.5 equivalent), toluene (40 ml) and water (4 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; after reaction, dibenzothiophene-4-boric acid (a compound shown in the formula D-5-2) (3.113 g, 1.05 equivalent), and then, the mixture was heated refluxly for 12 hours; after reaction, water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain an intermediate 4-1-A.sub.2 (6.175 g, total yield: 67%);

(100) (2) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-1-A.sub.2 (4.963 g, 1.0 equivalent), NBS (3.115 g, 2.5 equivalent), AIBN (0.006 g, 0.5 mol percent), and carbon tetrachloride (50 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 24 hours; after reaction, water (20 ml) was added to quench the reaction. After extraction with ethyl acetate (3*25 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain an intermediate 5-2 (5.047 g, yield: 83%).

(101) (3) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 5-2 (4.344 g, 1.0 equivalent), potassium hydroxide (0.842 g, 3.0 equivalent), and 1,2-dimethoxyethane (50 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 4 hours; after reaction, 2,4-dibromofuran (a compound shown in the formula E-2) (2.033 g, 1.8 equivalent), and then, the mixture was heated refluxly for 12 hours; after reaction, water (20 ml) was added to quench the reaction. After extraction with ethyl acetate (3*25 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain an intermediate 5-2-a (1.912 g, total yield: 41%).

(102) (4) In a dry, nitrogen-flushed 50-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 5-2-a (1.866 g, 1.0 equivalent), activated carbon supported palladium (5%, 0.106 g, 2.5 mol percent), and ethyl acetate (20 ml) were respectively added the mixture was stirred for 10 minutes, and finally, filling with hydrogen gas and the reaction was stirred for 8 hours at room temperature; water (15 ml) was added. After extraction with ethyl acetate (3*15 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain an intermediate 5-2-b (1.776 g, yield: 95%).

(103) (5) In a dry, nitrogen-flushed 50-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 5-2-b (1.500 g, 1.0 equivalent), p-toluenesulfonic acid (0.552 g, 2.0 equivalent), and toluene (15 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 16 hours; water (10 ml) was added. After extraction with ethyl acetate (3*10 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain an intermediate 5-2-c (1.441 g, yield: 98%).

(104) (6) In a dry, nitrogen-flushed 50-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 5-2-c (1.200 g, 1.0 equivalent) and anhydrous tetrahydrofuran (20 ml) were added, the mixture was stirred for 10 minutes at −78° C., subsequently, 2.5 M butyl lithium dissolved in hexane (1.31 ml, 2.5 equivalent) was added dropwise and the reaction was stirred for 30 minutes, and anhydrous acetone (0.24 ml, 2.5 equivalent) was added dropwise and the reaction was stirred for 2 hours; after reaction, a saturated sodium bicarbonate aqueous solution (10 ml) was added to quench the reaction. After extraction with ethyl acetate (3*15 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/15) to obtain an intermediate 5-2-d (0.974 g, yield: 85%).

(105) (7) In a dry, nitrogen-flushed 25-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 5-2-d (0.875 g, 1.0 equivalent) and anhydrous dichloromethane (10 ml) were added, the mixture was stirred for 10 minutes at 0° C., and subsequently, boron trifluoride diethyl ether (0.49 ml, 4.0 equivalent) was added dropwise and the reaction was stirred for 2 hours at room temperature; after reaction, a saturated sodium bicarbonate aqueous solution (10 ml) was added to quench the reaction. After extraction with ethyl acetate (3*15 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/25) to obtain the compound SA-24 (0.780 g, yield: 93%).

(106) Elemental analysis: (C.sub.60H.sub.42OSSi) theoretical values: C, 85.88; H, 5.05; O, 1.91; S, 3.82: measured values: C, 85.85; H, 5.07; O, 1.94; S, 3.83; HRMS (ESI) m/z (M.sup.+): theoretical value: 838.2726; measured value: 838.2732.

Embodiment 10

(107) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SA-26 below:

(108) ##STR00032##

(109) A synthesis route of the dibenzoheterocyclic compound shown in the formula SA-26 is as shown below:

(110) ##STR00033## ##STR00034##

(111) A preparation method of the dibenzoheterocyclic compound shown in the formula SA-26 includes the following steps:

(112) 1. Preparing an intermediate 4-1 by the synthesis method provided by the embodiment 1.

(113) 2. Preparing the dibenzoheterocyclic compound shown in the formula SA-26:

(114) (1) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-1 (5.582 g, 1.0 equivalent), the compound shown in the formula D-4 (5.844 g, 2.05 equivalent), Pd.sub.2(dba).sub.3 (0.275 g, 3 mol percent), potassium tert-butoxide (2.018 g, 2.1 equivalent), and anhydrous toluene (40 ml) were respectively added firstly, the mixture was stirred for 10 minutes, subsequently, tert-butyl phosphate dissolved in toluene (0.03 M, 10 ml) was added, and finally, the mixture was heated refluxly for 6 hours; after reaction, water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain an intermediate 4-1-A.sub.1 (9.716 g, yield: 94%).

(115) (2) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-1-A.sub.2 (4.963 g, 1.0 equivalent), NBS (3.115 g, 2.5 equivalent), AIBN (0.006 g, 0.5 mol percent), and carbon tetrachloride (50 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 24 hours; after reaction, water (20 ml) was added to quench the reaction. After extraction with ethyl acetate (3*25 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain an intermediate 5-3 (the intermediate 5-2 is the same as the intermediate 5-1 in the embodiment 8) (5.047 g, yield: 83%).

(116) (3) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 5-3 (4.774 g, 1.0 equivalent), potassium hydroxide (0.842 g, 3.0 equivalent), and 1,2-dimethoxyethane (50 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 4 hours; after reaction, 2-bromofuran (a compound shown in the formula E-3) (1.323 g, 1.8 equivalent), and then, the mixture was heated refluxly for 12 hours; after reaction, water (20 ml) was added to quench the reaction. After extraction with ethyl acetate (3*25 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain an intermediate 5-3-a (2.021 g, total yield: 43%).

(117) (4) In a dry, nitrogen-flushed 50-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 5-3-a (1.880 g, 1.0 equivalent), activated carbon supported palladium (5%, 0.106 g, 2.5 mol percent), and ethyl acetate (20 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, filling with hydrogen gas and the reaction was stirred for 8 hours at room temperature; water (15 ml) was added. After extraction with ethyl acetate (3*15 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain an intermediate 5-3-b (1.733 g, yield: 92%).

(118) (5) In a dry, nitrogen-flushed 50-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 5-3-b (1.500 g, 1.0 equivalent), p-toluenesulfonic acid (0.548 g, 2.0 equivalent), and toluene (15 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 16 hours; water (10 ml) was added. After extraction with ethyl acetate (3*10 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain an intermediate 5-3-c (1.457 g, yield: 99%).

(119) (6) In a dry, nitrogen-flushed 50-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 5-3-c (1.300 g, 1.0 equivalent), aniline (0.38 ml, 3.0 equivalent), Pd.sub.2(dba).sub.3 (0.039 g, 3 mol percent), dppf (0.006 g, 1 mol percent), potassium tert-butoxide (0.215 g, 2.1 equivalent), and anhydrous toluene (15 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 6 hours; after reaction, water (10 ml) was added to quench the reaction. After extraction with ethyl acetate (3*15 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/15) to obtain an intermediate 5-3-d (0.941 g, yield: 94%).

(120) (7) In a dry, nitrogen-flushed 25-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 5-3-d (0.936 g, 1.0 equivalent) and carbon tetrachloride (10 ml) were added firstly, the mixture was stirred for 10 minutes, and finally, irradiating the mixture for 72 hours by using an ultraviolet lamp; after reaction, water (10 ml) was added to quench the reaction. After extraction with ethyl acetate (3*15 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain the compound SA-26 (0.617 g, yield: 66%).

(121) Elemental analysis: (C.sub.68H.sub.47N.sub.3Si) theoretical values: C, 87.42; H, 5.07; N, 4.50; measured values: C, 87.45; H, 5.04; N, 4.52; HRMS (ESI) m/z (M.sup.+): theoretical value: 933.3539; measured value: 933.3532.

Embodiment 11

(122) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SA-34 below:

(123) ##STR00035##

(124) A synthesis route of the dibenzoheterocyclic compound shown in the formula SA-34 is as shown below:

(125) ##STR00036##

(126) A preparation method of the dibenzoheterocyclic compound shown in the formula SA-34 includes the following steps:

(127) 1. Preparing an intermediate 4-1 by the synthesis method provided by the embodiment 1.

(128) 2. Preparing the dibenzoheterocyclic compound shown in the formula SA-34:

(129) (1) In a dry, nitrogen-flushed 250-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-1 (5.582 g, 1.0 equivalent), 2-hydroxy-phenylboric acid (a compound shown in the formula D-6) (2.894 g, 2.3 equivalent), Pd(PPh.sub.3).sub.4 (0.578 g, 5 mol percent), sodium carbonate (2.649 g, 2.5 equivalent), toluene (120 ml) and water (12 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; after reaction, water (70 ml) was added to quench the reaction. After extraction with ethyl acetate (3*100 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/15) to obtain an intermediate 4-1-A.sub.3 (6.161 g, total yield: 87%).

(130) (2) In a dry, nitrogen-flushed 250-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 4-1-A.sub.3 (5.447 g, 1.0 equivalent) and anhydrous dichloromethane (100 ml) were added firstly, the mixture was stirred for 10 minutes at 0° C., and subsequently, boron trifluoride diethyl ether (6.17 ml, 5.0 equivalent) was added dropwise and the reaction was stirred for 2 hours at room temperature; after reaction, a saturated sodium bicarbonate aqueous solution (100 ml) was added to quench the reaction. After extraction with ethyl acetate (3*150 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/25) to obtain the compound SA-34 (5.137 g, yield: 95%).

(131) Elemental analysis: (C.sub.38H.sub.24O.sub.2Si) theoretical values: C, 84.41; H, 4.47; O, 5.92; measured values: C, 84.42; H, 4.43; O, 5.95; HRMS (E) m/z (M.sup.+): theoretical value: 540.1546; measured value: 540.1548.

Embodiment 12

(132) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SA-45 below:

(133) ##STR00037##

(134) A synthesis route of the dibenzoheterocyclic compound shown in the formula SA-45 is as shown below:

(135) ##STR00038##

(136) A preparation method of the dibenzoheterocyclic compound shown in the formula SA-45 includes the following steps:

(137) 1. Preparing an intermediate 4-1 by the synthesis method provided by the embodiment 1

(138) 2. Preparing the dibenzoheterocyclic compound having the structure as shown in formula SA-45:

(139) (1) In a dry, nitrogen-flushed 250-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-1 (5.582 g, 1.0 equivalent), benzeneseleninic acid anhydride (5.852 g, 1.25 equivalent), and chlorobenzene (120 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; and after reaction, reducing the temperature of a reaction solution to 0° C. and the mixture was filtered, then, the obtained solid was cleaned with hexane (3*80 ml), and a crude product was recrystallized with dichloromethane to obtain an intermediate 4-1-1 (4.957 g, yield: 83%).

(140) (2) In a dry, nitrogen-flushed 250-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, aniline (0.91 ml, 1.0 equivalent), benzaldehyde (1.06 ml, 1.05 equivalent), and ethanol (100 ml) were respectively added firstly, the mixture was stirred for 10 hours, subsequently, 7.5 M ammonium acetate was added to an aqueous solution (2.0 ml, 1.5 equivalent) the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 6 hours; after reaction, water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*150 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/25) to obtain an intermediate 4-1-2 (3.492 g, yield: 56%).

(141) (3) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-1-2 (3.118 g, 1.0 equivalent), K.sub.4[Fe(CN).sub.6] (0.634 g, 30 mol percent), palladium acetate (0.449 g, 40 mol percent), triphenylphosphine (0.131 g, 10 mol percent), sodium carbonate (0.106 g, 20 mol percent), and N,N-dimethyl formamide (30 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 16 hours; after reaction, water (20 ml) was added to quench the reaction. After extraction with ethyl acetate (3*25 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/25) to obtain the compound SA-45 (2.177 g, yield: 72%).

(142) Elemental analysis: (C.sub.41H.sub.28N.sub.4Si) theoretical values: C, 81.43; H, 4.67; N, 9.26; Si; measured values: C, 81.43; H, 4.64; N, 9.28; HRMS (ESI) m/z (M.sup.+): theoretical value: 604.2083; measured value: 604.2088.

Embodiment 13

(143) This embodiment provides an organic light-emitting device. As shown in FIG. 1, the organic light-emitting device includes an anode 1, a hole injection layer 2, a hole transport layer 3, a light-emitting layer 4, an electron transport layer 5, an electron injection layer 6 and a cathode 7 which are sequentially stacked on a substrate.

(144) In the organic light-emitting device, the anode is made from an ITO material; the cathode 7 is made from metal Al;

(145) the hole injection layer 2 is made from PEDOT:PSS, and the PEDOT:PSS has a chemical structure as shown below:

(146) ##STR00039##

(147) the hole transport layer 3 is made from NPB, and the NPB has a chemical structure as shown below:

(148) ##STR00040##

(149) the electron transport layer 5 is made from TPBI, and the TPBI has a chemical structure as shown below:

(150) ##STR00041##

(151) the electron injection layer 6 is formed by doping TPBI with an electron injection material LiF;

(152) a light-emitting material of the light-emitting layer 32 in the OLED is selected from the dibenzoheterocyclic compound shown in the formula SA-08:

(153) ##STR00042##

(154) the organic light-emitting device forms the following specific structure: ITO (anode)/PEDOT:PSS (hole injection layer, 30 nm)/NPB (hole transport layer, 40 nm)/SA-08 (light-emitting layer, 40 nm)/TPBI (electron transport layer, 40 nm)/TPBI: LiF (electron injection layer, 1 nm) aluminum (cathode, 150 nm).

(155) The light-emitting layer material is selected from the dibenzoheterocyclic compound SA-08, and Ar.sup.1 and Ar.sup.2 substituent groups in the compound SA-08 are phenyl groups, so that the compound SA-08 has a wide energy level band gap (E.sub.g=4.44 eV), deep blue light can be emitted (CIE, y<0.1), and a deep blue light-emitting device can be obtained. Because of the existence of the diphenyl ethylene group in the mother nucleus structure of the SA-08, the compound SA-08 has a low LUMO level (−1.52 eV), thereby being favorable for matching the energy level of the electron transport layer, and promoting injection and transport of electrons. Meanwhile, the dibenzoheterocyclic compound SA-08 is connected with a substituent group

(156) ##STR00043##
of an electron donor and two phenyl groups connected to the Si atom, material molecules have good hole transport performance, and the HOMO energy level is suitable for matching an adjacent hole transport layer, thereby being favorable for balancing electrons and holes in the light-emitting layer, increasing the combination probability of electrons and holes, and improving the blue light-emitting efficiency of the OLED. The spatial configuration of the dibenzoheterocyclic compound SA-08 is a butterfly configuration, thereby avoiding the generation of high energy excitons caused by stacking of the material molecules, effectively reducing the annihilation of the excitons in the light-emitting layer, avoiding the efficiency roll-off of the blue light-emitting device, preventing the deep blue color coordinate drift, and further obtaining the blue light-emitting device with high light-emitting stability. The HOMO energy level and the LUMO energy level of the dibenzoheterocyclic compound SA-08 are matched with the hole transport layer and the electron transport layer at two sides, thereby being favorable for lowering the potential barrier needing to be overcome by transporting electrons and holes to the light-emitting layer, and further lowering the working voltage of the device. On the other hand, the dibenzoheterocyclic compound shown in SA-08 has high thermal decomposition temperature, high thermal stability and morphological stability and excellent film-forming performance; the Ar.sup.1 and Ar.sup.2 substituent groups in the compound are phenyl groups, so that the rigidity of the compound SA-08 is enhanced, and the thermal stability of the compound SA-08 is further improved; and as a light-emitting layer material, the compound SA-08 is not easy to decompose and crystallize, thereby further improving the performance and the light-emitting efficiency of the OLED.

(157) As an alternative embodiment, the guest light-emitting material of the light-emitting layer can also be selected from any dibenzoheterocyclic compound shown in the formula (SA-01) to the formula (SA-45).

(158) As an alternative embodiment, the guest light-emitting material of the light-emitting layer can also be selected from any other dibenzoheterocyclic compound having a chemical structure shown in the general formula (I).

Embodiment 14

(159) This embodiment provides an organic light-emitting device, which is different from the organic light-emitting device provided in the embodiment 13 only in that the light-emitting layer material is selected from the dibenzoheterocyclic compound having a structure shown below:

(160) ##STR00044##

Embodiment 15

(161) This embodiment provides an organic light-emitting device, which is different from the organic light-emitting device provided in the embodiment 13 only in that the light-emitting layer material is selected from the dibenzoheterocyclic compound having a structure shown below:

(162) ##STR00045##

Embodiment 16

(163) This embodiment provides an organic light-emitting device, which is different from the organic light-emitting device provided in the embodiment 13 only in that the light-emitting layer material is selected from the dibenzoheterocyclic compound having a structure shown below:

(164) ##STR00046##

Embodiment 17

(165) This embodiment provides an organic light-emitting device, which is different from the organic light-emitting device provided in the embodiment 13 only in that the light-emitting layer material is selected from the dibenzoheterocyclic compound having a structure shown below:

(166) ##STR00047##

(167) Contrast 1

(168) This contrast provides an organic light-emitting device, which is different from the OLED provided in the embodiment 12 only in that the light-emitting layer material is selected from the compound having a structure shown below:

(169) ##STR00048##

(170) Test Case 1

(171) 1. Measurement of thermal decomposition temperature (T.sub.d) of dibenzoheterocyclic compound

(172) A thermal gravimetric analyzer (TGA) is used for testing the thermal decomposition temperature of the material of the invention, the test range is from room temperature to 600° C., the heating rate is 10° C./min, and under the nitrogen atmosphere, the temperature with the weight loss of 0.5% is defined as the thermal decomposition temperature.

(173) 2. Measurement of HOMO energy level and LUMO energy level of dibenzoheterocyclic compound

(174) An electrochemical workstation is used for testing the HOMO and LUMO energy levels of the material of the invention through a cyclic voltammetry (CV), a platinum filament (PT) is used as a counter electrode, and silver/silver chloride (Ag/AgCl) is used as a reference electrode. Under the nitrogen atmosphere, a test is carried out in a dichloromethane electrolyte containing 0.1 M tetrabutylammonium hexafluorophosphate at a scanning rate of 100 mV/s, potential calibration is performed by ferrocene, and an absolute HOMO energy level of the potential of the ferrocene in a vacuum state is set to ˜4.8 eV:
HOMO=−[E.sub.onset.sup.ox−E.sub.Fc/Fc++4.8]eV;
LUMO=−[E.sub.onset.sup.red−E.sub.Fc/Fc++4.8]eV.

(175) TABLE-US-00001 TABLE 1 Compound SA-08 SA-11 SA-24 SA-26 SA-34 SA-45 T.sub.d (° C.) 456 469 471 477 464 461 HOMO(eV) −5.96 −6.13 −5.91 −5.01 −5.82 −5.43 LUMO(eV) −1.52 −1.58 −1.63 −1.49 −1.92 −2.01

(176) According to the test data in the table 1, the dibenzoheterocyclic compound provided by the invention has high thermal decomposition temperature, and has higher thermal stability after film formation, material molecules are not easy to decompose or crystallize along with heat generated during the use of a device, the functions of a light-emitting layer can be kept stable, the breakdown of the device can be avoided, and the service life of the device can be prolonged. Meanwhile, the dibenzoheterocyclic compound has a low LUMO energy level (−1.49 to −1.92 eV), thereby being favorable for injecting and transporting electrons to the light-emitting layer and increasing the electron ratio. Because the hole transport performance of a semiconductor material is generally higher than the electron transport performance of the semiconductor material, the dibenzoheterocyclic compound is favorable for balancing electrons and holes, and the light-emitting efficiency of the device is improved. Because the band gap between the HOMO energy level and the LUMOenergy level of the dibenzoheterocyclic compound is wide (−3.52 to −4.55 eV), light can be emitted in a deep blue light-emitting region, and a deep blue light-emitting device can be obtained. Meanwhile, the dibenzoheterocyclic compound can serve as a host material of the light-emitting layer so as to perform efficient energy transfer to a guest light-emitting material.

(177) Test Case 2

(178) The properties, such as current, voltage, brightness and luminescent spectrum, of the organic light emitting diode provided by the embodiment 13 to the embodiment 17 and the contrast 1 are synchronously tested by adopting a PR 650 spectral scanning brightness meter and a Keithley K 2400 digital source meter system. Test results are as shown in table 2.

(179) TABLE-US-00002 TABLE 2 Current Yield of external Dibenzoheterocyclic density/ fluorescence Chroma/ compound Voltage/V mA/cm.sup.2 quantums/% CIE (X, Y) Contrast 1 7.8 20 4.35 (0.15, 0.24) Embodiment 13 SA-08 4.9 20 6.70 (0.14, 0.09) Embodiment 14 SA-11 4.7 20 5.92 (0.14, 0.11) Embodiment 15 SA-24 4.5 20 6.94 (0.15, 0.10) Embodiment 16 SA-34 4.4 20 6.01 (0.15, 0.12) Embodiment 17 SA-45 4.5 20 5.54 (0.15, 0.11)

(180) According to the table 2, as the light-emitting layer material, the dibenzoheterocyclic compound provided by the invention is favorable for lowering the working voltage of the device and improving the light-emitting efficiency of the device, and a deep blue light-emitting device which is high in yield of external quantums, capable of emitting light efficiently and stable in device performance can be obtained.

(181) Obviously, the above embodiments are only used for clearly explaining examples but not limiting the embodiments. Other changes or modifications of different forms can also be made by those of ordinary skill in the art on the basis of the above illustration. There is no need and no way to exhaust all embodiments. Derived obvious changes or modifications are still within the protection scope of the invention.