Nitrogen-containing compound, electronic element and electronic apparatus

Abstract

The present application relates to the technical field of organic materials, and provides a nitrogen-containing compound, an electronic element and an electronic apparatus. The structure of the nitrogen-containing compound is shown as Chemical formula 1. The nitrogen-containing compound can improve the performance of the electronic element. Ar is II, and X is selected from O or S; L.sub.1 is III, and in L.sub.1, “#” represents a connection point between the phenylene of L.sub.1 and N, and “##” represents a connection point between the phenylene of L.sub.1 and IV; L.sub.2 is V, and in L.sub.2, “#” represents a connection point between the phenylene of L.sub.2 and N, and “##” represents a connection point between the phenylene of L.sub.2 and R.sub.4. ##STR00001##

Claims

1. A nitrogen-containing compound, wherein the structure of the nitrogen-containing compound is shown as Chemical formula 1: ##STR00779## wherein Ar is selected from 2-DBF, 3-DBF, 2-DBT or 3-DBT; and the structural formulas of 2-DBF, 3-DBF, 2-DBT and 3-DBT are as follows: ##STR00780## L.sub.1 is ##STR00781## and in L.sub.1, “#” represents a connection point between the phenylene of L.sub.1 and N, and “##” represents a connection point between the phenylene of L.sub.1 and ##STR00782## L.sub.2 is ##STR00783## and in L.sub.2, “#” represents a connection point between the phenylene of L.sub.2 and N, and “##” represents a connection point between the phenylene of L.sub.2 and R.sub.4; R.sub.1 is selected from methyl or phenyl; R.sub.2 is selected from methyl or phenyl; R.sub.3 is selected from H and the groups shown in CA1, CA6 to CA10; R.sub.4 is selected from phenyl and the substituents shown in CA1, CA6 to CA10; only one of R.sub.3 and R.sub.4 is selected from the substituents shown in CA1, CA6 to CA10; where the structures of CA1, CA6 to CA10 are as follows: ##STR00784##

2. The nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound is selected from the group consisting of various compounds listed in the following table: TABLE-US-00004 Substituent of compound Ar L.sub.1 R.sub.3 R.sub.4 L.sub.2 Compound 115 2-DBF CA6  Ph Compound 116 2-DBF CA9  Ph Compound 117 2-DBF CA10 Ph Compound 133 2-DBF CA1  Ph Compound 155 2-DBF CA1  Ph Compound 160 2-DBF CA6  Ph Compound 163 2-DBF CA9  Ph Compound 164 2-DBF CA10 Ph Compound 167 2-DBF CA1  Ph Compound 172 2-DBF CA6  Ph Compound 173 2-DBF CA8  Ph Compound 174 2-DBF CA9  Ph Compound 176 2-DBF CA1  Ph Compound 180 2-DBF CA6  Ph Compound 181 2-DBF CA7  Ph Compound 182 2-DBF CA8  Ph Compound 183 2-DBF CA9  Ph Compound 184 2-DBF CA10 Ph Compound 199 2-DBF CA7  Ph Compound 208 2-DBF CA4  Ph Compound 218 2-DBF H CA1  Compound 223 2-DBF H CA6  Compound 224 2-DBF H CA7  Compound 225 2-DBF H CA8  Compound 226 2-DBF H CA9  Compound 255 2-DBF H CA6  Compound 256 2-DBF H CA7  Compound 257 2-DBF H CA8  Compound 258 2-DBF H CA9  Compound 259 2-DBF H CA10 Compound 262 2-DBF H CA1  Compound 267 2-DBF H CA6  Compound 268 2-DBF H CA7  Compound 269 2-DBF H CA8  Compound 270 2-DBF H CA9  Compound 271 2-DBF H CA10 Compound 274 2-DBF H CA1  Compound 279 2-DBF H CA6  Compound 280 2-DBF H CA7  Compound 281 2-DBF H CA8  Compound 282 2-DBF H CA9  Compound 283 2-DBF H CA10 Compound 408 3-DBF CA1  Ph Compound 412 3-DBF CA7  Ph Compound 413 3-DBF CA8  Ph Compound 414 3-DBF CA9  Ph Compound 451 3-DBF CA1  Ph Compound 457 3-DBF CA7  Ph Compound 458 3-DBF CA9  Ph Compound 459 3-DBF CA10 Ph Compound 462 3-DBF CA1  Ph Compound 466 3-DBF CA10 Ph Compound 468 3-DBF CA8  Ph Compound 469 3-DBF CA9  Ph Compound 470 3-DBF CA10 Ph Compound 471 3-DBF CA1  Ph Compound 476 3-DBF CA6  Ph Compound 477 3-DBF CA7  Ph Compound 478 3-DBF CA8  Ph Compound 479 3-DBF CA9  Ph Compound 480 3-DBF CA10 Ph Compound 510 3-DBF CA6  Ph Compound 512 3-DBF CA8  Ph Compound 520 3-DBF H CA1  Compound 525 3-DBF H CA6  Compound 526 3-DBF H CA7  Compound 527 3-DBF H CA8  Compound 528 3-DBF H CA9  Compound 529 3-DBF H CA10 Compound 562 3-DBF H CA6  Compound 563 3-DBF H CA7  Compound 564 3-DBF H CA8  Compound 565 3-DBF H CA9  Compound 566 3-DBF H CA10 Compound 569 3-DBF H CA1  Compound 574 3-DBF H CA6  Compound 575 3-DBF H CA7  Compound 576 3-DBF H CA8  Compound 577 3-DBF H CA9  Compound 578 3-DBF H CA10 Compound 581 3-DBF H CA1  Compound 586 3-DBF H CA6  Compound 587 3-DBF H CA8  Compound 588 3-DBF H CA9  Compound 589 3-DBF H CA10 Compound 613 3-DBF H CA1  Compound 643 3-DBF H CA7  Compound 725 2-DBT CA1  Ph Compound 730 2-DBT CA6  Ph Compound 731 2-DBT CA7  Ph Compound 732 2-DBT CA8  Ph Compound 737 2-DBT CA9  Ph Compound 738 CA10 Ph Compound 782 2-DBT CA1  Ph Compound 787 2-DBT CA6  Ph Compound 788 2-DBT CA7  Ph Compound 789 2-DBT CA8  Ph Compound 790 2-DBT CA9  Ph Compound 791 2-DBT CA10 Ph Compound 795 2-DBT CA1  Ph Compound 800 2-DBT CA6  Ph Compound 801 2-DBT CA7  Ph Compound 802 2-DBT CA8  Ph Compound 803 2-DBT CA9  Ph Compound 804 2-DBT CA10 Ph Compound 807 2-DBT CA1  Ph Compound 812 2-DBT CA6  Ph Compound 813 2-DBT CA7  Ph Compound 814 2-DBT CA8  Ph Compound 815 2-DBT CA9  Ph Compound 816 2-DBT CA10 Ph Compound 857 2-DBT H CA1  Compound 864 2-DBT H CA6  Compound 866 2-DBT H CA7  Compound 867 2-DBT H CA8  Compound 868 2-DBT H CA9  Compound 869 2-DBT H CA10 Compound 901 2-DBT H CA1  Compound 906 2-DBT H CA6  Compound 907 2-DBT H CA7  Compound 908 2-DBT H CA8  Compound 909 2-DBT H CA10 Compound 912 2-DBT H CA1  Compound 917 2-DBT H CA6  Compound 918 2-DBT H CA7  Compound 919 2-DBT H CA8  Compound 920 2-DBT H CA9  Compound 921 2-DBT H CA10 Compound 924 2-DBT H CA1  Compound 930 2-DBT H CA6  Compound 931 2-DBT H CA7  Compound 932 2-DBT H CA8  Compound 933 2-DBT H CA9  Compound 934 2-DBT H CA10 Compound 937 3-DBF CA6  Ph Compound 938 3-DBF CA7  Ph Compound 941 2-DBF H CA1  Compound 945 2-DBT H CA9  Compound 995 2-DBF H CA10  Compound 1027 3-DBT CA8  Ph  Compound 1047 2-DBF CA7  Ph  Compound 1048 2-DBF CA8  Ph  Compound 1083 2-DBF CA10 Ph  Compound 1086 3-DBT CA1  Ph  Compound 1092 3-DBT CA6  Ph  Compound 1093 3-DBT CA7  Ph  Compound 1094 3-DBT CA8  Ph  Compound 1095 3-DBT CA9  Ph  Compound 1096 3-DBT CA10 Ph  Compound 1137 3-DBT CA1  Ph  Compound 1142 3-DBT CA6  Ph  Compound 1143 3-DBT CA7  Ph  Compound 1144 3-DBT CA8  Ph  Compound 1145 3-DBT CA9  Ph  Compound 1146 3-DBT CA10 Ph  Compound 1149 3-DBT CA1  Ph  Compound 1155 3-DBT CA6  Ph  Compound 1156 3-DBT CA7  Ph  Compound 1157 3-DBT CA8  Ph  Compound 1158 3-DBT CA9  Ph  Compound 1159 3-DBT CA10 Ph  Compound 1162 3-DBT CA1  Ph  Compound 1169 3-DBT CA6  Ph  Compound 1170 3-DBT CA7  Ph  Compound 1171 3-DBT CA8  Ph  Compound 1172 3-DBT CA9  Ph  Compound 1173 3-DBT CA10 Ph  Compound 1218 3-DBT H CA1   Compound 1223 3-DBT H CA6   Compound 1224 3-DBT H CA7   Compound 1227 3-DBT H CA8   Compound 1228 3-DBT H CA9   Compound 1229 3-DBT H CA10  Compound 1258 3-DBT H CA1   Compound 1263 3-DBT H CA6   Compound 1264 3-DBT H CA7   Compound 1265 3-DBT H CA8   Compound 1266 3-DBT H CA9   Compound 1267 3-DBT H CA10  Compound 1270 3-DBT H CA1   Compound 1276 3-DBT H CA6   Compound 1277 3-DBT H CA7   Compound 1278 3-DBT H CA8   Compound 1279 3-DBT H CA9   Compound 1280 3-DBT H CA10  Compound 1283 3-DBT H CA1   Compound 1288 3-DBT H CA6   Compound 1289 3-DBT H CA7   Compound 1290 3-DBT H CA8   Compound 1291 3-DBT H CA9   Compound 1294 3-DBT H CA10

3. An electronic element, comprising an anode and a cathode which are arranged oppositely, and a functional layer arranged between the anode and the cathode, wherein the functional layer contains the nitrogen-containing compound according to claim 1.

4. The electronic element according to claim 3, wherein the functional layer comprises a hole transporting layer, and the hole transporting layer contains the nitrogen-containing compound.

5. The electronic element according to claim 4, wherein the hole transporting layer comprises a first hole transporting layer and a second hole transporting layer; the first hole transporting layer is arranged to be closer to the surface of the anode than the second hole transporting layer; and the first hole transporting layer or the second hole transporting layer contains the nitrogen-containing compound.

6. The electronic element according to claim 5, wherein the second hole transporting layer consists of the nitrogen-containing compound.

7. The electronic element according to claim 5, wherein the electronic element is a photoelectric conversion device or an organic electroluminescent device.

8. An electronic apparatus, comprising the electronic element according to claim 3.

9. An electronic element, comprising an anode and a cathode which are arranged oppositely, and a functional layer arranged between the anode and the cathode, wherein the functional layer contains the nitrogen-containing compound according to claim 2.

10. The electronic element according to claim 9, wherein the functional layer comprises a hole transporting layer, and the hole transporting layer contains the nitrogen-containing compound.

11. The electronic element according to claim 10, wherein the hole transporting layer comprises a first hole transporting layer and a second hole transporting layer; the first hole transporting layer is arranged to be closer to the surface of the anode than the second hole transporting layer; and the first hole transporting layer or the second hole transporting layer contains the nitrogen-containing compound.

12. The electronic element according to claim 11, wherein the second hole transporting layer consists of the nitrogen-containing compound.

13. The electronic element according to claim 11, wherein the electronic element is a photoelectric conversion device or an organic electroluminescent device.

14. An electronic apparatus, comprising the electronic element according to claim 9.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) The above and other features and advantages of the present disclosure will become more apparent by describing the exemplary embodiments in detail with reference to the accompanying drawings.

(2) FIG. 1 is a structural schematic diagram of an organic electroluminescent device according to the embodiments of the present disclosure.

(3) FIG. 2 is a structural schematic diagram of an electronic apparatus according to the embodiments of the present disclosure.

(4) FIG. 3 is a structural schematic diagram of a photoelectric conversion device according to the embodiments of the present disclosure.

(5) FIG. 4 is a structural schematic diagram of an electronic apparatus according to the embodiments of the present disclosure.

(6) FIG. 5 shows H-NMR of Compound 392.

(7) FIG. 6 shows the synthetic route of Compound 1.

(8) Description of reference signs of main element in the drawings is as follows:

(9) 100. Anode; 200. Cathode; 300. Functional layer; 310. Hole injecting layer; 320. Hole transporting layer; 321. First hole transporting layer; 322. Second hole transporting layer; 330. Organic light-emitting layer; 340. Electron transporting layer; 350. Electron injecting layer; 360. Photoelectric conversion layer; 400. Electronic apparatus; 500. Electronic apparatus.

DETAILED DESCRIPTION

(10) Exemplary embodiments are now described more comprehensively with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in various forms and should not be construed as being limited to the examples described herein; on the contrary, these embodiments are provided, so that the present disclosure will be more comprehensive and complete, and the concept of the exemplary embodiments will be completely conveyed to those skilled in the art. The features, structures, or characteristics described may be combined in one or more embodiments in any suitable manner. In the following description, numerous specific details are provided to give a sufficient understanding of the embodiments of the present disclosure.

(11) In the drawings, the area and layers thickness may be exaggerated for clarity. In the drawings, the same reference sign denotes the same or similar structure, and thus their detailed description will be omitted.

(12) In the present disclosure, the aryl group refers to optional functional groups or substituents derived from aromatic rings. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. In other words, the aryl group may be a monocyclic aryl group, a fused aryl group, two or more monocyclic aryl groups conjugated through carbon-carbon bonds, a monocyclic aryl group and a fused aryl group conjugated through carbon-carbon bonds, and two or more fused aryl groups conjugated through carbon-carbon bonds. That is, the two or more aryl groups conjugated through carbon-carbon bonds may also be regarded as aryl groups of the present disclosure. Among them, the aryl group does not contain heteroatoms such as B, N, O, S or P. For example, biphenyl and terphenyl and the like are the aryl groups in the present disclosure. The examples of the aryl group include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pyrenyl, chrysenyl and the like.

(13) In the present disclosure, the heteroaryl group may be a heteroaryl group including at least one of B, O, N, P, Si and S as a heteroatom. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, the heteroaryl group may be a single aromatic ring system, and may also be a plurality of aromatic ring systems conjugated through carbon-carbon bonds; and any one aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. The specific examples of the heteroaryl group include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzosilyl, dibenzofuranyl, phenyl-substituted dibenzofuranyl, dibenzofuranyl-substituted phenyl, and the like.

(14) In the present disclosure, the description manners “are each independently . . . ”, “. . . are respectively independently” and “ . . . are independently selected from” are interchangeable and should be understood in a broad sense, which may mean that the specific options expressed between the same symbols in different groups do not affect each other, or may mean that the specific options expressed between the same symbols in the same group do not affect each other.

(15) In the present disclosure, the non-located connection bond refers to a single bond “” extending from the ring system, which means that one end of the connection bond may be connected to any position in the ring system through which the bond penetrates and the other end may be connected to other parts of the compound molecule. For example, as shown in the following formula (X′), phenanthryl represented by the formula (X′) is connected to other positions of the molecule through a non-located connection bond extending from the middle of the benzene ring at one side, and its meaning includes any possible connection manner shown in formulae (X′-1) to (X′-4).

(16) ##STR00008##

(17) According to a first aspect, the present disclosure provides a nitrogen-containing compound having a structure shown as follows:

(18) ##STR00009##

(19) wherein Ar is

(20) ##STR00010##
and X is selected from O or S, that is, Ar is

(21) ##STR00011##

(22) L.sub.1 is

(23) ##STR00012##
and in L.sub.1, and “##” represents a connection point between the phenylene of L.sub.1 and

(24) ##STR00013##

(25) L.sub.2 is

(26) ##STR00014##
and in L.sub.2, “#” represents a connection point between the phenylene of L.sub.2 and N, and “##” represents a connection point between the phenylene of L.sub.2 and R.sub.4.

(27) R.sub.1 is selected from methyl or phenyl; R.sub.2 is selected from methyl or phenyl.

(28) R.sub.3 is selected from H and the groups shown in CA1 to CA10; R.sub.4 is selected from phenyl and the substituents shown in CA1 to CA10; only one of R.sub.3 and R.sub.4 is selected from the substituents shown in CA1 to CA10; where the structures of CA1 to CA10 are as follows:

(29) ##STR00015##

(30) For example, in the compound

(31) ##STR00016##
Ar is

(32) ##STR00017##
L.sub.1 is

(33) ##STR00018##
L.sub.2 is

(34) ##STR00019##
R.sub.1 is phenyl, R.sub.2 is methyl, R.sub.3 is H, and R.sub.4 is

(35) ##STR00020##

(36) The nitrogen-containing compound of the present disclosure has a dibenzofuran group or a dibenzothiophene group, and the dibenzofuran group or the dibenzothiophene group has strong electron dissociation energy, so the HOMO energy level of the nitrogen-containing compound can be effectively reduced, this allows the hole transporting layer to inject holes into the organic light-emitting layer serving as the energy conversion layer more smoothly, or allows the photoelectric conversion layer serving as the energy conversion layer to inject holes into the electron transporting layer more smoothly, and the nitrogen-containing compound has good hole transporting efficiency. In this way, the voltage performance and the efficiency performance of the electronic element applying the nitrogen-containing compound can be effectively improved. For example, the luminous efficiency of the organic electroluminescent device can be improved, the driving voltage of the organic electroluminescent device can be reduced, the photoelectric efficiency and the open-circuit voltage of the photoelectric conversion device can also be improved. The introduction of the dibenzofuran group or the dibenzothiophene group may increase a conjugate plane of the nitrogen-containing compound of the present application, and may also cause intermolecular stacking and crystallization to shorten the life of the device. In order to overcome the possible adverse effect of the dibenzofuran group or the dibenzothiophene group, part of the nitrogen-containing compound of the present application also introduces a cycloalkane structure with large steric hindrance, and the cycloalkane group can effectively reduce the stacking effect of the nitrogen-containing compound of the present application and can improve the film-forming performance of the nitrogen-containing compound. The preparation and test results of the organic electroluminescent device show that the introduction of the cycloalkane group prolongs the life of the organic electroluminescent device, which indicates that the adverse effect of the dibenzofuran group or the dibenzothiophene group is overcome, the film-forming performance of the nitrogen-containing compound is effectively improved, the planarity of the nitrogen-containing compound itself is reduced, particularly the intermolecular stacking effect of the nitrogen-containing compound is reduced, so that the life of the electronic element applying the nitrogen-containing compound of the present application is prolonged. Therefore, the nitrogen-containing compound of the present application has better hole transporting performance, lower HOMO energy level, lower intermolecular stacking effects and more excellent film-forming performance, and can improve the voltage performance, efficiency performance and life performance of the electronic element such as the photoelectric conversion device and the electroluminescent device.

(37) More importantly, in the compound of the present application, a specific substituent is introduced at the ortho-position of the nitrogen atom on the aryl group, so that the planarity of the triarylamine core group can be reduced, the HOMO energy level can be further improved, and the intermolecular stacking effect can be reduced. Therefore, the nitrogen-containing compound of the present application is suitable for the hole transporting layer of the organic electroluminescent device, particularly suitable for the second hole transporting layer of the organic electroluminescent device, so that the driving voltage drop of the organic electroluminescent device can be reduced, the current efficiency, the power efficiency and the external quantum efficiency of the organic electroluminescent device can be improved, and the life of the organic electroluminescent device can be prolonged.

(38) Optionally, Ar is selected from 2-DBF, 3-DBF, 2-DBT or 3-DBT, wherein the structural formulas of 2-DBF, 3-DBF, 2-DBT and 3-DBT are as follows:

(39) ##STR00021##

(40) Optionally, the nitrogen-containing compound is selected from the group consisting of various compounds listed in the Table 1:

(41) TABLE-US-00001 TABLE 1 Substituent of compound Ar L.sub.1 R.sub.3 R.sub.4 L.sub.2 Compound 111 2-DBF CA2 Ph Compound 112 2-DBF CA3 Ph Compound 113 2-DBF CA4 Ph Compound 114 2-DBF CA5 Ph Compound 115 2-DBF 0 CA6 Ph Compound 116 2-DBF CA9 Ph Compound 117 2-DBF CA10 Ph Compound 133 2-DBF CA1 Ph Compound 155 2-DBF CA1 Ph Compound 156 2-DBF 0 CA2 Ph Compound 157 2-DBF CA3 Ph Compound 158 2-DBF CA4 Ph Compound 159 2-DBF CA5 Ph Compound 160 2-DBF CA6 Ph Compound 161 2-DBF 0 CA7 Ph Compound 162 2-DBF CA8 Ph Compound 163 2-DBF CA9 Ph Compound 164 2-DBF CA10 Ph Compound 167 2-DBF CA1 Ph Compound 168 2-DBF 0 CA2 Ph Compound 169 2-DBF CA3 Ph Compound 170 2-DBF CA4 Ph Compound 171 2-DBF CA5 Ph Compound 172 2-DBF CA6 Ph Compound 173 2-DBF 0 CA8 Ph Compound 174 2-DBF CA9 Ph Compound 176 2-DBF CA1 Ph Compound 177 2-DBF CA2 Ph Compound 178 2-DBF CA3 Ph Compound 179 2-DBF 0 CA5 Ph Compound 180 2-DBF CA6 Ph Compound 181 2-DBF CA7 Ph Compound 182 2-DBF CA8 Ph Compound 183 2-DBF CA9 Ph Compound 184 2-DBF 0 CA10 Ph Compound 199 2-DBF CA7 Ph Compound 208 2-DBF CA4 Ph Compound 218 2-DBF H CA1 Compound 219 2-DBF H CA2 Compound 220 2-DBF 00 H CA3 01 Compound 221 2-DBF 02 H CA4 03 Compound 222 2-DBF 04 H CA5 05 Compound 223 2-DBF 06 H CA6 07 Compound 224 2-DBF 08 H CA7 09 Compound 225 2-DBF 0 H CA8 Compound 226 2-DBF H CA9 Compound 253 2-DBF H CA4 Compound 254 2-DBF H CA5 Compound 255 2-DBF H CA6 Compound 256 2-DBF 0 H CA7 Compound 257 2-DBF H CA8 Compound 258 2-DBF H CA9 Compound 259 2-DBF H CA10 Compound 262 2-DBF H CA1 Compound 263 2-DBF 0 H CA2 Compound 264 2-DBF H CA3 Compound 265 2-DBF H CA4 Compound 266 2-DBF H CA5 Compound 267 2-DBF H CA6 Compound 268 2-DBF 0 H CA7 Compound 269 2-DBF H CA8 Compound 270 2-DBF H CA9 Compound 271 2-DBF H CA10 Compound 274 2-DBF H CA1 Compound 275 2-DBF 0 H CA2 Compound 276 2-DBF H CA3 Compound 277 2-DBF H CA4 Compound 278 2-DBF H CA5 Compound 279 2-DBF H CA6 Compound 280 2-DBF 0 H CA7 Compound 281 2-DBF H CA8 Compound 282 2-DBF H CA9 Compound 283 2-DBF H CA10 Compound 408 3-DBF CA1 Ph Compound 409 3-DBF 0 CA2 Ph Compound 410 3-DBF CA3 Ph Compound 411 3-DBF CA6 Ph Compound 412 3-DBF CA7 Ph Compound 413 3-DBF CA8 Ph Compound 414 3-DBF 0 CA9 Ph Compound 451 3-DBF CA1 Ph Compound 452 3-DBF CA2 Ph Compound 453 3-DBF CA3 Ph Compound 454 3-DBF CA4 Ph Compound 455 3-DBF 0 CA5 Ph Compound 457 3-DBF CA7 Ph Compound 458 3-DBF CA9 Ph Compound 459 3-DBF CA10 Ph Compound 462 3-DBF CA1 Ph Compound 463 3-DBF 00 CA2 Ph 01 Compound 464 3-DBF 02 CA3 Ph 03 Compound 465 3-DBF 04 CA4 Ph 05 Compound 466 3-DBF 06 CA10 Ph 07 Compound 467 3-DBF 08 CA5 Ph 09 Compound 468 3-DBF 0 CA8 Ph Compound 469 3-DBF CA9 Ph Compound 470 3-DBF CA10 Ph Compound 471 3-DBF CA1 Ph Compound 472 3-DBF CA2 Ph Compound 473 3-DBF 0 CA3 Ph Compound 474 3-DBF CA4 Ph Compound 475 3-DBF CA5 Ph Compound 476 3-DBF CA6 Ph Compound 477 3-DBF CA7 Ph Compound 478 3-DBF 0 CA8 Ph Compound 479 3-DBF CA9 Ph Compound 480 3-DBF CA10 Ph Compound 510 3-DBF CA6 Ph Compound 512 3-DBF CA8 Ph Compound 520 3-DBF 0 H CA1 Compound 521 3-DBF H CA2 Compound 522 3-DBF H CA3 Compound 523 3-DBF H CA4 Compound 524 3-DBF H CA5 Compound 525 3-DBF 0 H CA6 Compound 526 3-DBF H CA7 Compound 527 3-DBF H CA8 Compound 528 3-DBF H CA9 Compound 529 3-DBF H CA10 Compound 532 3-DBF 0 H CA1 Compound 558 3-DBF H CA2 Compound 559 3-DBF H CA3 Compound 560 3-DBF H CA4 Compound 561 3-DBF H CA5 Compound 562 3-DBF 0 H CA6 Compound 563 3-DBF H CA7 Compound 564 3-DBF H CA8 Compound 565 3-DBF H CA9 Compound 566 3-DBF H CA10 Compound 569 3-DBF 0 H CA1 Compound 570 3-DBF H CA2 Compound 571 3-DBF H CA3 Compound 572 3-DBF H CA4 Compound 573 3-DBF H CA5 Compound 574 3-DBF 0 H CA6 Compound 575 3-DBF H CA7 Compound 576 3-DBF H CA8 Compound 577 3-DBF H CA9 Compound 578 3-DBF H CA10 Compound 581 3-DBF 00 H CA1 01 Compound 582 3-DBF 02 H CA2 03 Compound 583 3-DBF 04 H CA3 05 Compound 584 3-DBF 06 H CA4 07 Compound 585 3-DBF 08 H CA5 09 Compound 586 3-DBF 0 H CA6 Compound 587 3-DBF H CA8 Compound 588 3-DBF H CA9 Compound 589 3-DBF H CA10 Compound 613 3-DBF H CA1 Compound 643 3-DBF 0 H CA7 Compound 725 2-DBT CA1 Ph Compound 726 2-DBT CA2 Ph Compound 727 2-DBT CA3 Ph Compound 728 2-DBT CA4 Ph Compound 729 2-DBT 0 CA5 Ph Compound 730 2-DBT CA6 Ph Compound 731 2-DBT CA7 Ph Compound 732 2-DBT CA8 Ph Compound 736 2-DBF H CA3 Compound 737 2-DBT 0 CA9 Ph Compound 738 2-DBT CA10 Ph Compound 782 2-DBT CA1 Ph Compound 783 2-DBT CA2 Ph Compound 784 2-DBT CA3 Ph Compound 785 2-DBT 0 CA4 Ph Compound 786 2-DBT CA5 Ph Compound 787 2-DBT CA6 Ph Compound 788 2-DBT CA7 Ph Compound 789 2-DBT CA8 Ph Compound 790 2-DBT 0 CA9 Ph Compound 791 2-DBT CA10 Ph Compound 795 2-DBT CA1 Ph Compound 796 2-DBT CA2 Ph Compound 797 2-DBT CA3 Ph Compound 798 2-DBT 0 CA4 Ph Compound 799 2-DBT CA5 Ph Compound 800 2-DBT CA6 Ph Compound 801 2-DBT CA7 Ph Compound 802 2-DBT CA8 Ph Compound 803 2-DBT 0 CA9 Ph Compound 804 2-DBT CA10 Ph Compound 807 2-DBT CA1 Ph Compound 808 2-DBT CA2 Ph Compound 809 2-DBT CA3 Ph Compound 810 2-DBT 0 CA4 Ph Compound 811 2-DBT CA5 Ph Compound 812 2-DBT CA6 Ph Compound 813 2-DBT CA7 Ph Compound 814 2-DBT CA8 Ph Compound 815 2-DBT 00 CA9 Ph 01 Compound 816 2-DBT 02 CA10 Ph 03 Compound 857 2-DBT 04 H CA1 05 Compound 858 2-DBT 06 H CA2 07 Compound 859 2-DBT 08 H CA3 09 Compound 860 2-DBT 0 H CA4 Compound 861 2-DBT H CA5 Compound 864 2-DBT H CA6 Compound 866 2-DBT H CA7 Compound 867 2-DBT H CA8 Compound 868 2-DBT 0 H CA9 Compound 869 2-DBT H CA10 Compound 881 3-DBF CA4 Ph Compound 882 3-DBF CA5 Ph Compound 901 2-DBT H CA1 Compound 902 2-DBT 0 H CA2 Compound 903 2-DBT H CA3 Compound 904 2-DBT H CA4 Compound 905 2-DBT H CA5 Compound 906 2-DBT H CA6 Compound 907 2-DBT 0 H CA7 Compound 908 2-DBT H CA8 Compound 909 2-DBT H CA10 Compound 912 2-DBT H CA1 Compound 913 2-DBT H CA2 Compound 914 2-DBT 0 H CA3 Compound 915 2-DBT H CA4 Compound 916 2-DBT H CA5 Compound 917 2-DBT H CA6 Compound 918 2-DBT H CA7 Compound 919 2-DBT 0 H CA8 Compound 920 2-DBT H CA9 Compound 921 2-DBT H CA10 Compound 924 2-DBT H CA1 Compound 925 2-DBT H CA2 Compound 927 2-DBT 0 H CA3 Compound 928 2-DBT H CA4 Compound 929 2-DBT H CA5 Compound 930 2-DBT H CA6 Compound 931 2-DBT H CA7 Compound 932 2-DBT 0 H CA8 Compound 933 2-DBT H CA9 Compound 934 2-DBT H CA10 Compound 937 3-DBF CA6 Ph Compound 938 3-DBF CA7 Ph Compound 941 2-DBF 0 H CA1 Compound 942 2-DBF H CA2 Compound 945 2-DBT H CA9 Compound 995 2-DBF H CA10 Compound 1027 3-DBT CA8 Ph Compound 1047 2-DBF 00 CA7 Ph 01 Compound 1048 2-DBF 02 CA8 Ph 03 Compound 1083 2-DBF 04 CA10 Ph 05 Compound 1086 3-DBT 06 CA1 Ph 07 Compound 1088 3-DBT 08 CA2 Ph 09 Compound 1089 3-DBT 0 CA3 Ph Compound 1090 3-DBT CA4 Ph Compound 1091 3-DBT CA5 Ph Compound 1092 3-DBT CA6 Ph Compound 1093 3-DBT CA7 Ph Compound 1094 3-DBT 0 CA8 Ph Compound 1095 3-DBT CA9 Ph Compound 1096 3-DBT CA10 Ph Compound 1137 3-DBT CA1 Ph Compound 1138 3-DBT CA2 Ph Compound 1139 3-DBT 0 CA3 Ph Compound 1140 3-DBT CA4 Ph Compound 1141 3-DBT CA5 Ph Compound 1142 3-DBT CA6 Ph Compound 1143 3-DBT CA7 Ph Compound 1144 3-DBT 0 CA8 Ph Compound 1145 3-DBT CA9 Ph Compound 1146 3-DBT CA10 Ph Compound 1149 3-DBT CA1 Ph Compound 1150 3-DBT CA2 Ph Compound 1151 3-DBT 0 CA3 Ph Compound 1153 3-DBT CA4 Ph Compound 1154 3-DBT CA5 Ph Compound 1155 3-DBT CA6 Ph Compound 1156 3-DBT CA7 Ph Compound 1157 3-DBT 0 CA8 Ph Compound 1158 3-DBT CA9 Ph Compound 1159 3-DBT CA10 Ph Compound 1162 3-DBT CA1 Ph Compound 1163 3-DBT CA2 Ph Compound 1166 3-DBT 0 CA3 Ph Compound 1167 3-DBT CA4 Ph Compound 1168 3-DBT CA5 Ph Compound 1169 3-DBT CA6 Ph Compound 1170 3-DBT CA7 Ph Compound 1171 3-DBT 0 CA8 Ph Compound 1172 3-DBT CA9 Ph Compound 1173 3-DBT CA10 Ph Compound 1189 3-DBT H CA1 Compound 1218 3-DBT H CA1 Compound 1219 3-DBT 0 H CA2 Compound 1220 3-DBT H CA3 Compound 1221 3-DBT H CA4 Compound 1222 3-DBT H CA5 Compound 1223 3-DBT H CA6 Compound 1224 3-DBT 00 H CA7 01 Compound 1227 3-DBT 02 H CA8 03 Compound 1228 3-DBT 04 H CA9 05 Compound 1229 3-DBT 06 H CA10 07 Compound 1258 3-DBT 08 H CA1 09 Compound 1259 3-DBT 0 H CA2 Compound 1260 3-DBT H CA3 Compound 1261 3-DBT H CA4 Compound 1262 3-DBT H CA5 Compound 1263 3-DBT H CA6 Compound 1264 3-DBT 0 H CA7 Compound 1265 3-DBT H CA8 Compound 1266 3-DBT H CA9 Compound 1267 3-DBT H CA10 Compound 1270 3-DBT H CA1 Compound 1271 3-DBT 0 H CA2 Compound 1273 3-DBT H CA3 Compound 1274 3-DBT H CA4 Compound 1275 3-DBT H CA5 Compound 1276 3-DBT H CA6 Compound 1277 3-DBT 0 H CA7 Compound 1278 3-DBT H CA8 Compound 1279 3-DBT H CA9 Compound 1280 3-DBT H CA10 Compound 1283 3-DBT H CA1 Compound 1284 3-DBT 0 H CA2 Compound 1285 3-DBT H CA3 Compound 1286 3-DBT H CA4 Compound 1287 3-DBT H CA5 Compound 1288 3-DBT H CA6 Compound 1289 3-DBT 0 H CA7 Compound 1290 3-DBT H CA8 Compound 1291 3-DBT H CA9 Compound 1294 3-DBT H CA10

(42) For example, according to Table 1, in Compound 1294, Ar is 3-DBT, L.sub.1 is

(43) ##STR00668##
L.sub.2

(44) ##STR00669##
R.sub.3 is H, and R.sub.4 is CA10. The structural formula of Compound 1294 is:

(45) ##STR00670##

(46) According to a second aspect, the present disclosure also provides an electronic element. The electronic element comprises an anode and a cathode which are arranged oppositely, and a functional layer arranged between the anode and the cathode, wherein the functional layer contains the nitrogen-containing compound provided in the first aspect of the present disclosure.

(47) The nitrogen-containing compound provided by the present disclosure may be used to form at least one organic membrane layer of the functional layer so as to improve the voltage characteristic, efficiency characteristic and life characteristic of the electronic element.

(48) Optionally, the organic membrane layer containing the nitrogen-containing compound of the present disclosure is located between the anode and the energy conversion layer of the electronic element, so that hole transport between the anode and the energy conversion layer is improved.

(49) Optionally, the functional layer includes a hole transporting layer, and the hole transporting layer contains the nitrogen-containing compound provided by the present disclosure. Where the hole transporting layer may consist of the nitrogen-containing compound provided by the present disclosure, and may also consist of the nitrogen-containing compound provided by the present disclosure and other materials jointly.

(50) According to one embodiment, the hole transporting layer includes a first hole transporting layer and a second hole transporting layer, and the first hole transporting layer is arranged closer to the surface of the anode relative to the second hole transporting layer. The first hole transporting layer and/or the second hole transporting layer contains the nitrogen-containing compound provided by the present disclosure. In other words, one layer of the first hole transporting layer and the second hole transporting layer may contain the nitrogen-containing compound provided by the present disclosure, or both the first hole transporting layer and the second hole transporting layer may contain the nitrogen-containing compound provided by the present disclosure. It may be understood that the first hole transporting layer and the second hole transporting layer may also contain other materials, or may also not contain other materials. Optionally, the second hole transporting layer consists of the nitrogen-containing compound.

(51) According to one preferred embodiment, as shown in FIG. 1, the electronic element is an organic electroluminescent device. The organic electroluminescent device includes an anode 100, a first hole transporting layer 321, a second hole transporting layer 322, an organic light-emitting layer 330 serving as the energy conversion layer, an electron transporting layer 340 and a cathode 200 which are sequentially stacked. The nitrogen-containing compound provided by the present disclosure may be applied to the second hole transporting layer 322 of the organic electroluminescent device, so as to prolong the life of the organic electroluminescent device, improve the luminous efficiency of the organic electroluminescent device and reduce the driving voltage of the organic electroluminescent device.

(52) In the present disclosure, the anode 100 includes an anode material, preferably a material with a large work function and facilitating hole injection into the functional layer. The specific examples of the anode material include, but are not limited to, metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof, metal oxides such as zinc oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combination of metals and oxides such as ZnO:Al or SnO.sub.2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline. A transparent electrode containing indium tin oxide (ITO) as an anode is preferably included.

(53) Optionally, the first hole transporting layer 321 includes one or more hole transporting materials. The hole transporting material may be selected from a carbazole polymer, a carbazole linked triarylamine compound or other types of compounds, which is not particularly limited in the present disclosure. For example, the first hole transporting layer 321 may consist of compound NPB.

(54) Optionally, the organic light-emitting layer 330 is composed of a single light-emitting material, or also contains a host material and a guest material. In one specific embodiment, the organic light-emitting layer 330 consists of a host material and a guest material. Holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 may be combined in the organic light-emitting layer 330 to form excitons, the excitons transfer energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.

(55) The host material of the organic light-emitting layer 330 may be a metal-chelated compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which is not particularly limited in the present disclosure. In one embodiment of the present disclosure, the host material of the organic light-emitting layer 330 may be CBP.

(56) The guest material of the organic light-emitting layer 330 may be a compound with a condensed aryl ring or a derivative thereof, a compound with heteroaryl ring or a derivative thereof, and an aromatic amine derivative or other materials, which is not particularly limited in the present disclosure. In one embodiment of the present disclosure, the guest material of the organic light-emitting layer 330 may be green phosphorescent material, and may be, for example, Ir(ppy).sub.3 and the like.

(57) The electron transporting layer 340 may be of a single-layer structure, or may also be of a multi-layer structure, which may include one or more electron transporting materials. The electron transporting materials may be selected from, but is not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transporting materials. In one embodiment of the present disclosure, the electron transporting layer 340 may consist of DBimiBphen and LiQ.

(58) In the present disclosure, the cathode 200 includes a cathode material, which is a material with a small work function and facilitating electron injection into the functional layer. The specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multi-layer materials such as LiF/Al, Liq/Al, LiO.sub.2/Al, LiF/Ca, LiF/Al and BaF.sub.2/Ca. A metal electrode containing aluminum as a cathode is preferably included.

(59) Optionally, as shown in FIG. 1, a hole injecting layer 310 is also be provided between the anode 100 and the first hole transporting layer 321, so as to enhance the capability of injecting holes into the first hole transporting layer 321. The hole injecting layer 310 may choose benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which is not particularly limited in the present disclosure. For example, the hole injecting layer 310 may consist of m-MTDATA.

(60) Optionally, as shown in FIG. 1, an electron injecting layer 350 is also be provided between the cathode 200 and the electron transporting layer 340, so as to enhance the capability of injecting electrons into the electron transporting layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfide and alkali metal halide, or may include complexes of alkali metal and organic matter. For example, the electron injecting layer 350 may include LiQ.

(61) According to another preferred embodiment, the electronic element is a photoelectric conversion device. As shown in FIG. 3, the photoelectric conversion device includes an anode 100 and a cathode 200 which are arranged oppositely, and a functional layer 300 arranged between the anode 100 and the cathode 200, wherein the functional layer 300 contains the nitrogen-containing compound provided by the present disclosure.

(62) According to one embodiment, as shown in FIG. 3, the functional layer 300 includes a hole transporting layer 320, and the hole transporting layer 320 contains the nitrogen-containing compound provided by the present disclosure. The hole transporting layer 320 may consist of the nitrogen-containing compound provided by the present disclosure, and may also consist of the nitrogen-containing compound provided by the present disclosure and other materials jointly.

(63) Optionally, the hole transporting layer 320 also includes inorganic doped materials, so that the hole transporting performance of the hole transporting layer 320 can be improved.

(64) According to one specific embodiment, as shown in FIG. 3, the photoelectric conversion device includes an anode 100, a hole transporting layer 320, a photoelectric conversion layer 360, an electron transporting layer 340 and a cathode 200 which are sequentially stacked.

(65) Optionally, the photoelectric conversion device is a solar battery, and particularly is an organic thin film solar battery. For example, in one embodiment of the present disclosure, the solar battery includes an anode, a hole transporting layer, a photoelectric conversion layer, an electron transporting layer and a cathode which are sequentially stacked, where the hole transporting layer contains the nitrogen-containing compound provided by the present disclosure.

(66) According to a third aspect of the present disclosure, the embodiments of the present disclosure also provide an electronic apparatus. The electronic apparatus includes any one electronic element described by the embodiments of the electronic element provided in the second aspect of the present disclosure. The electronic apparatus has any one electronic element described by the embodiments of the electronic element, so the electronic apparatus has the same beneficial effects, which will not be elaborated here.

(67) For example, as shown in FIG. 2, the present disclosure provides an electronic apparatus 400. The electronic apparatus 400 includes any one organic electroluminescent device described by the above embodiments of the organic electroluminescent device. The electronic apparatus 400 may be a display apparatus, a lighting apparatus, an optical communication apparatus, or other types of electronic apparatus. For example, the electronic apparatus 400 may include, but is not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting, and an optical module, etc. The electronic apparatus 400 has any one organic electroluminescent device described by the above embodiments of the organic electroluminescent device, so the electronic apparatus 400 has the same beneficial effects, which will not be elaborated here.

(68) For another example, as shown in FIG. 4, the present disclosure provides an electronic apparatus 500. The electronic apparatus 500 includes any one photoelectric conversion device described by the above embodiments of the photoelectric conversion device. The electronic apparatus 500 may be a solar power generation equipment, a photodetector, a fingerprint identification equipment, an optical module, a CCD camera, or other types of electronic apparatus. The electronic apparatus 500 has any one photoelectric conversion device described by the above embodiments of the photoelectric conversion device, so the electronic apparatus 500 has the same beneficial effects, which will not be elaborated here.

(69) Hereinafter, the present disclosure is further described in detail through the examples. However, the following examples are only illustration of the present disclosure, and does not limit the present disclosure.

(70) The following synthesis examples 1 to 22 are used to describe the compounds and the preparation method thereof.

Synthesis Example 1

(71) According to the synthetic route shown in FIG. 6, Compound 1 was synthesized:

(72) Reactant 1 (50.0 g, 520 mmol) and trifluoroacetic acid (TFA) (400 mL) were added into a 1 L round-bottom flask, concentrated nitric acid (1.5 g) was added under a stirring condition, the temperature was raised to 45-50° C., and the mixture was stirred for 16 hours in an air atmosphere; trifluoroacetic acid was removed under reduced pressure, an ethanol solution (500 mL) of 10 wt % potassium hydroxide was added into the remaining mixture, and stirring was performed for 3 hours; ethanol was removed under reduced pressure, methylene chloride was added into the flask, the organic phase was washed with water twice, then dried over anhydrous magnesium sulfate, and the solvent in the organic phase was removed under reduced pressure to obtain a crude product; and the obtained crude product was purified through silica gel column chromatography by using methylene chloride/normal heptane as an eluent to obtain a white powdered intermediate 1 (19.4 g, a yield of 33%).

(73) The intermediate 1 (19.0 g, 169 mmol), reactant 2 (39.5 g, 169 mmol) and methylene chloride (MC) (250 mL) were added into a 500 mL round-bottom flask, and trifluoromethanesulfonic acid (HOTf) (38.1 g, 254 mmol) was added dropwise at −15 to −20° C. under the protection of nitrogen; after dropwise adding, low-temperature stirring was maintained for 8 hours, then the temperature was raised to room temperature (25° C.), and a 10 wt % sodium hydroxide aqueous solution was added into the reaction liquid slowly and dropwise to be neutral; an organic phase was separated and was washed with water twice, the organic phase was dried over anhydrous magnesium sulfate, and the solvent in the organic phase was removed under reduced pressure to obtain a crude product; and the obtained crude product was purified through silica gel column chromatography by using normal heptane as an eluent to obtain a white solid intermediate 2 (34.4 g, a yield of 62%).

(74) Reactant 3 (10.0 g, 64 mmol), reactant 4 (2-amino-dibenzofuran) (12.8 g, 70 mmol), tris(dibenzylideneacetone)dipalladium (Pd.sub.2(dba).sub.3) (0.6 g, 0.6 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos) (0.6 g, 1.3 mmol) and sodium tert-butoxide (tBuONa) (9.2 g, 96 mmol) were added into methylbenzene (150 mL), and the mixture was heated to 105-110° C. under the protection of nitrogen and stirred for 1 hour; then the mixture was cooled to room temperature, and reaction liquid was washed with water twice, dried by adding magnesium sulfate, and filtered, the obtained filtrate was allowed to pass through a short silica gel column, and then the liquid passing through the column was decompressed to remove the solvent to obtain a crude product; and the obtained crude product was purified by recrystallization with a methylene dichloride/ethanol system to obtain a light brown solid intermediate 3 (13.2 g, a yield of 80%).

(75) The intermediate 2 (4.0 g, 12.2 mmol), the intermediate 3 (3.2 g, 12.2 mmol), tris(dibenzylideneacetone)dipalladium (0.1 g, 0.1 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos) (0.1 g, 0.2 mmol) and sodium tert-butoxide (1.8 g, 18.3 mmol) were added into methylbenzene (40 mL), and the mixture was heated to 105-110° C. under the protection of nitrogen and stirred for 16 hours; then the mixture was cooled to room temperature, reaction liquid was washed with water, dried by adding magnesium sulfate, and filtered, the obtained filtrate was allowed to pass through a short silica gel column, and then the liquid passing through the column was decompressed to remove the solvent to obtain a crude product; and the obtained crude product was purified by recrystallization with a methylene dichloride/normal heptane system to obtain a white solid Compound 1 (2.3 g, a yield of 37%). Mass spectrum: m/z=506.2[M+H].sup.+.

Synthesis Examples 2 to 22

(76) Referring to the method of Compound 1, the compounds listed in Table 2 were synthesized respectively in the synthesis examples 2 to 22, except that the reactant 1 was replaced with reactant A, the reactant 2 was replaced with reactant B, the reactant 3 was replaced with reactant C, and the reactant 4 was replaced with reactant D, where the structural formulas of the reactants and the corresponding compounds, and the yield, the final yield and mass spectrum characterization result of the compounds are shown in Table 2.

(77) TABLE-US-00002 TABLE 2 Structure, raw material, yield and mass spectrum characterization of various compounds Compound Reactant Reactant Reactant Reactant m/z Number A B C D Compound structure Yield (%) [M + H].sup.+ Compound  51 25 596.3 Compound 126 0 32 624.3 Compound 133 39 610.3 Compound 199 0 48 712.4 Compound 208 54 762.4 Compound 229 00 30 520.3 Compound 243 01 02 03 04 05 59 534.3 Compound 327 06 07 08 09 0 50 520.3 Compound 392 36 622.3 Compound 466 0 40 664.4 Compound 510 40 700.4 Compound 613 0 30 596.3 Compound 643 44 698.3 Compound 774 0 41 640.3 Compound 865 38 522.2 Compound 926 0 27 612.3 Compound 945 43 652.3 Compound 1087  0 54 652.3 Compound 1253  38 640.3 Compound 269 0 43 636.3 Compound 521 37 548.3

(78) The NMR spectrum of the compound 392 is as shown in FIG. 5, .sup.1H NMR (CDCl.sub.3, 400 MHz): 7.80 (d, 1H), 7.59 (d, 1H), 7.49-7.45 (m, 3H), 7.41-7.33 (m, 9H), 7.28 (t, 1H), 7.19 (d, 2H), 7.09-7.03 (m, 4H), 6.96 (d, 2H), 6.90 (d, 1H), 2.12 (s, 3H), 1.95 (s, 6H), 1.82-1.76 (m, 6H).

(79) The following examples are used to describe the application of the compounds of the present disclosure to organic electroluminescent devices.

Example 1

(80) A green organic electroluminescent device was prepared by the following method.

(81) An ITO substrate (made by Corning) with an ITO thickness of 1500 Å was cut into a size of 40 mm(length)×40 mm(width)×0.7 mm(thickness), and was prepared into an experimental substrate with cathode, anode and insulating layer patterns by the photoetching process, and surface treatment was performed by ultraviolet ozone and O.sub.2:N.sub.2 plasma to increase the work function of the anode (the experimental substrate) and remove scum.

(82) m-MTDATA was subjected to vacuum evaporation on the experimental substrate (the anode) to form a hole injecting layer (HIL) with a thickness of 100 Å, and NPB was subjected to vacuum evaporation on the hole injecting layer to form a first hole transporting layer with a thickness of 1000 Å.

(83) Compound 1 was subjected to vacuum evaporation on the first hole transporting layer to form a second hole transporting layer with a thickness of 400 Å.

(84) CBP as a host material and Ir(ppy).sub.3 as a guest material were subjected to evaporation at the same time according to a film thickness ratio of 100:8 to form a light-emitting layer (EML) with a thickness of 350 Å.

(85) DBimiBphen and LiQ were mixed and evaporated according to a weight ratio of 1:1 to form an electron transporting layer (ETL) with a thickness of 300 Å.

(86) LiQ was evaporated on the electron transporting layer to form an electron injecting layer (EIL) with a thickness of 10 Å.

(87) Magnesium (Mg) and silver (Ag) were mixed at an evaporation rate of 1:9 and were subjected to vacuum evaporation on the electron injecting layer to form a cathode with a thickness of 120 Å.

(88) CP-1 was evaporated with a thickness of 650 Å on the cathode, thereby the preparation of the green organic electroluminescent device was completed.

(89) The structural formulas of m-MTDATA, NPB, CBP, Ir(ppy).sub.3, DBimiBphen, LiQ and CP-1 are as follows:

(90) ##STR00776## ##STR00777##

Examples 2 to 22

(91) The green organic electroluminescent device was prepared according to the method in Example 1, except that in Examples 2 to 22, the second hole transporting layer material (that is, Compound 1) in Example 1 was replaced with compounds listed in Table 3, respectively, so that the corresponding green organic electroluminescent devices were prepared. For example, in Example 2, Compound 1 in Example 1 was replaced with Compound 51, and the green organic electroluminescent device was prepared according to the same method as that in Example 1.

Comparative Example 1

(92) Compound 1 in Example 1 was replaced with the compound TCTA, and a green organic electroluminescent device was prepared according to the same method as that in Example 1. The structural formula of TCTA is:

(93) ##STR00778##

(94) For the green organic electroluminescent devices prepared in Examples 1 to 22 and Comparative example 1, the performance of the devices was tested under the condition of 10 mA/cm.sup.2, the T95 lifetime of the devices was tested under a constant current density of 20 mA/cm.sup.2. The test results are shown in Table 3.

(95) TABLE-US-00003 TABLE 3 Performance test results of the organic electroluminescent devices External Second hole quantum transporting Driving Current Power efficiency T95 Serial layer voltage efficiency efficiency (EQE) lifetime number material (V) (Cd/A) (lm/W) CIE.sub.x CIE.sub.y (%) (h) Example 1 Compound 1 3.71 76.7 65.0 0.220 0.730 15.6 306 Example 2 Compound 3.63 81.8 70.8 0.220 0.730 17.0 335 51 Example 3 Compound 3.75 70.9 59.4 0.220 0.730 14.3 320 126 Example 4 Compound 4.02 86.9 67.9 0.220 0.730 20.9 360 133 Example 5 Compound 4.01 86.5 67.8 0.220 0.730 20.8 375 199 Example 6 Compound 3.99 84.2 66.3 0.220 0.730 20.2 352 208 Example 7 Compound 3.83 72.2 59.2 0.220 0.730 14.2 316 229 Example 8 Compound 3.77 65.6 54.7 0.220 0.730 13.1 322 243 Example 9 Compound 3.99 73.4 57.8 0.220 0.730 13.9 315 327 Example 10 Compound 3.67 69.1 59.1 0.220 0.730 14.2 292 392 Example 11 Compound 4.01 88.1 69.0 0.220 0.730 21.1 358 466 Example 12 Compound 3.97 84.6 67.0 0.220 0.730 20.3 351 510 Example 13 Compound 3.90 86.8 69.9 0.220 0.730 20.8 364 613 Example 14 Compound 4.05 87.9 68.1 0.220 0.730 21.1 362 643 Example 15 Compound 3.83 76.8 63.0 0.220 0.730 15.1 300 774 Example 16 Compound 3.82 71.6 58.9 0.220 0.730 14.2 292 865 Example 17 Compound 3.96 67.4 53.5 0.220 0.730 12.9 323 926 Example 18 Compound 3.98 86.3 68.1 0.220 0.730 20.7 346 945 Example 19 Compound 3.61 69.2 60.2 0.22 0.730 16.6 311 1087 Example 20 Compound 3.66 69.1 59.3 0.22 0.730 16.6 305 1253 Example 21 Compound 3.99 88.0 69.3 0.22 0.730 21.1 361 269 Example 22 Compound 3.95 86.5 68.8 0.22 0.730 20.8 367 521 Comparative TCTA 4.22 52.7 39.2 0.22 0.730 12.7 210 example 1

(96) It can be seen from Table 3 that compared with the organic electroluminescent device prepared in Comparative example 1, for the organic electroluminescent devices in Examples 1 to 22, the driving voltage is reduced by about 4%-14%, the current efficiency is increased by about 24%-67%, the power efficiency is increased by about 36%-81%, the external quantum efficiency is increased by about 3.1%-66%, and the life is increased by about 39%-79%. In addition, compared with other examples, the organic electroluminescent devices in Examples 4 to 5, 11 to 14, 18 and 21 to 22 also have longer life and higher efficiency, for example, the lifetime is maximally increased by 28%, and the current efficiency is maximally increased by 34%.

(97) Part of the nitrogen-containing compound structure of the present disclosure introduces cycloalkane with the three-dimensional structure and dibenzofuran/dibenzothiophene into the triarylamine basic structure at the same time. The dibenzofuran/dibenzothiophene group has stronger electron dissociation energy, which can effectively reduce the HOMO energy level of the material, so that the holes can be injected into the green light-emitting layer more smoothly, the driving voltage of the organic electroluminescent device is effectively reduced, and the luminous efficiency is improved, but this type structure has a larger conjugate plane, which may cause intermolecular stacking and crystallization to reduce the life of the device. Through the introduction of the three-dimensional cycloalkane with large steric hindrance, the stacking effect is effectively reduced, the film-forming performance of the material is greatly improved, and the life of the device is not reduced, but is prolonged. In addition, in the preferred embodiment of the present application, a specific substituent is introduced at the ortho-position of the nitrogen atom on the aryl group, so that the planarity of the triarylamine core group can be reduced, the HOMO energy level can be further improved, and the intermolecular stacking effect can be reduced. Therefore, the nitrogen-containing compound of the present application is suitable for the hole transporting layer of the organic electroluminescent device, particularly suitable for the second hole transporting layer of the organic electroluminescent device, so that the driving voltage drop of the organic electroluminescent device can be reduced, the current efficiency, the power efficiency and the external quantum efficiency of the organic electroluminescent device can be improved, and the life of the organic electroluminescent device can be prolonged.

(98) It should be understood that the present disclosure does not limit the application to the detailed structure and the arrangement manner of the parts provided in the description. The present disclosure can have other embodiments, and can be implemented and performed in various manners. The aforementioned variation and modification forms should fall within the scope of the present application. It should be understood that the present application disclosed and defined in the description extends to all replaceable combinations of two or more independent features mentioned or obvious herein and/or in the accompanying drawings. All the different combinations form a plurality of replaceable aspects of the present disclosure. The embodiments described in the description illustrate the known preferred manners for implementing the present disclosure, and those skilled in the art can utilize the present disclosure.