NITROGEN-CONTAINING COMPOUND, ORGANIC ELECTROLUMINESCENT DEVICE, AND ELECTRONIC APPARATUS

20250101024

18/552363

February 27, 2023

The application relates to the technical field of organic electroluminescent materials, and provides a nitrogen-containing compound, and an organic electroluminescent device and an electronic apparatus including the nitrogen-containing compound. The compound of the application has a core structure that is an indolocarbazolyl group fused with cyclohexane. The compound, when used as a host material of an light emitting layer, can improve balance of charge carriers in the light emitting layer, expand a region where the carriers recombine, improve generation and utilization efficiency of excitons as well as luminescence efficiency and service life of the device.

1. A nitrogen-containing compound having a structure formed by fusing a structure of the following Formula 1 and a structure of the following Formula 2 together, wherein the structure of Formula 2 is fused via * to positions of any two adjacent * on Ring B in the structure of Formula 1; [chemical expression included] Ring A is benzocyclohexane; Ring C is selected from an C6-14 aromatic ring; groups A1 and A2 are each independently selected from a structure shown in Formula a-1 or a structure shown in Formula a-2, and at least one of A1 and A2 is the structure shown in Formula a-1; [chemical expression included] L, L1, L2 and L3 are identical or different, and are each independently selected from a single bond, a substituted or unsubstituted C6-30 arylene, or a substituted or unsubstituted C3-30 heteroarylene; Ar3 is selected from a substituted or unsubstituted C6-40 aryl, or a substituted or unsubstituted C3-40 heteroaryl; Het is a C3-20 nitrogen-containing heteroarylene; Ar1 and Ar2 are identical or different, and are each independently selected from hydrogen, a substituted or unsubstituted C6-40 aryl, or a substituted or unsubstituted C3-40 heteroaryl; each R1, each R2 and each R3 are identical or different, and are each independently selected from deuterium, a cyano, a halogen, an C1-10 alkyl, a C1-10 haloalkyl, a C1-10 deuterated alkyl, a C3-12 trialkylsilyl, a triphenylsilyl, an C6-20 aryl, a C6-20 deuterated aryl, a C6-20 halogenated aryl, a C3-20 heteroaryl or a C3-10 cycloalkyl; and optionally, any two adjacent R2s form a 6-membered to 14-membered aromatic ring, the 6-membered to 14-membered aromatic ring being optionally substituted by zero, one, two, three, four, five or six R4s; each R4 is independently selected from deuterium, a cyano, a halogen, an C1-10 alkyl, a C1-10 haloalkyl, a C1-10 deuterated alkyl, or a C3-12 trialkylsilyl; n1 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; n2 is selected from 0, 1 or 2; n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; substituents of L, L1, L2, L3, Ar1, Ar2 and Ar3 are identical or different, and are each independently selected from deuterium, a cyano, a halogen, an C1-10 alkyl, a C1-10 haloalkyl, a C1-10 deuterated alkyl, a C3-12 trialkylsilyl, a triphenylsilyl, an C6-20 aryl, a C6-20 deuterated aryl, a C6-20 halogenated aryl, a C3-20 heteroaryl or a C3-10 cycloalkyl; and optionally, any two adjacent substituents may form a saturated or unsaturated 3-membered to 15-membered ring.

2. The nitrogen-containing compound according to claim 1, wherein the structure of Formula 1 is selected from structures shown in the following Formulae (i-1)-(i-3): [chemical expression included]

3. The nitrogen-containing compound according to claim 1, wherein Ring C is selected from a benzene ring, a naphthalene ring, or a phenanthrene ring.

4. The nitrogen-containing compound according to claim 1, wherein each R1, each R2 and each R3 are identical or different, and are each independently selected from deuterium, a cyano, a fluorine, a trideuteromethyl, a trimethylsilyl, a trifluoromethyl, a cyclopentyl, a cyclohexyl, an adamantly, a methyl, an ethyl, an isopropyl, a tert-butyl, a phenyl or a naphthyl; optionally, any two adjacent R2s form a benzene ring, the benzene ring being substituted by zero, one, two, three, four, five or six R4s; and each R4 is each independently selected from deuterium, a cyano, a fluorine, a trideuteromethyl or a trifluoromethyl.

5. The nitrogen-containing compound according to claim 1, wherein Het is selected from the following groups: [chemical expression included] wherein represents a bond linked with L; represents a bond linked with L1; represents a bond linked with L2; where a formula contains no it means that, in [chemical expression included] linked at this position, L2 is a single bond and Ar2 is hydrogen.

6. The nitrogen-containing compound according to claim 1, wherein Het is selected from the following groups: [chemical expression included] [chemical expression included] wherein represents a bond linked with L; represents a bond linked with L1; represents a bond linked with L2; where a formula contains no it means that, in [chemical expression included] linked at this position, L2 is a single bond and Ar2 is hydrogen.

7. The nitrogen-containing compound according to claim 1, wherein L, L1, L2 and L3 are identical or different, and are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted fluorenylidene, a substituted or unsubstituted pyridylidene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted carbazolylene; alternatively, substituents of L, L1, L2 and L3 are identical or different, and are each independently selected from deuterium, a fluorine, a cyano, a methyl, an ethyl, an isopropyl, a tert-butyl, a trifluoromethyl, a trideuteromethyl, a trimethylsilyl or a phenyl.

8. The nitrogen-containing compound according to claim 1, wherein Ar1 and Ar3 are each independently selected from a substituted or unsubstituted C6-25 aryl or a substituted or unsubstituted C7-20 heteroaryl; and Ar2 is selected from hydrogen, a substituted or unsubstituted C6-25 aryl, or a substituted or unsubstituted C7-20 heteroaryl; alternatively, substituents of Ar1, Ar2 and Ar3 are each independently selected from deuterium, a halogen, a cyano, a C1-4 haloalkyl, a C1-4 deuterated alkyl, an C1-4 alkyl, a C5-10 cycloalkyl, an C6-12 aryl, a C5-12 heteroaryl or a C3-8 trialkylsilyl; and optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

9. The nitrogen-containing compound according to claim 1, wherein: Ar1 and Ar3 are each independently selected from substituted or unsubstituted groups V; and Ar2 is selected from hydrogen and substituted or unsubstituted groups V; wherein the unsubstituted groups V are selected from the following groups: [chemical expression included] [chemical expression included] [chemical expression included] [chemical expression included] [chemical expression included] the substituted groups V each have one or more substituents, the substituents of the groups V being each independently selected from deuterium, a fluorine, a cyano, a trideuteromethyl, a trimethylsilyl, a trifluoromethyl, a cyclopentyl, a cyclohexyl, an adamantly, a methyl, an ethyl, an isopropyl, a tert-butyl, a phenyl, a naphthyl, a pyridyl, a dibenzofuranyl, a dibenzothiophenyl, a carbazolyl, a benzoxazolyl or a benzothiazolyl, and when each group V has more than one substituents, the substituents are identical or different.

10. The nitrogen-containing compound according to claim 1, wherein at least one of A1 and A2 is the structure shown in Formula a-1, the structure [chemical expression included] in Formula a-1 being selected from the following groups: [chemical expression included] [chemical expression included] [chemical expression included] [chemical expression included] [chemical expression included] [chemical expression included] [chemical expression included]

11. The nitrogen-containing compound according to claim 1, wherein [chemical expression included] is selected from the following groups, and [chemical expression included] is selected from hydrogen or the following groups: [chemical expression included] [chemical expression included]

12. 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13. An organic electroluminescent device, comprising an anode and a cathode that are disposed facing each other, and a functional layer disposed between the anode and the cathode, wherein the functional layer comprises the nitrogen-containing compound according to claim 1; alternatively, the functional layer comprises an organic light emitting layer, the organic light emitting layer comprising the nitrogen-containing compound.

14. An electronic apparatus, comprising the organic electroluminescent device according to claim 13.

07; 07; 07; 09; 10

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