Compounds of formula (I) and their use in organic electronic devices

Abstract

This invention relates to compounds of formula (I) and their use in organic electronic devices.

Description

Detailed description of the invention

[0001] [Technical Field] The present invention relates to a compound of formula (I) for use in organic electronic devices, an organic semiconductor layer containing the compound of formula (I), an organic electronic device containing the organic semiconductor layer, and a display device containing the organic electronic device.

[0002] [Background technology] Organic electronic devices such as organic light-emitting diodes (OLEDs) are self-emissive devices that possess a wide viewing angle, excellent contrast, fast response, high brightness, superior operating voltage characteristics, and excellent color reproduction. A typical OLED includes an anode, a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and a cathode, which are sequentially stacked on a substrate. Of these, the HTL, EML, and ETL are thin films formed from organic compounds.

[0003] When a voltage is applied to the anode and cathode, holes injected from the anode move to the EML via the HTL, and electrons injected from the cathode move to the EML via the ETL. The holes and electrons recombine in the EML to generate excitons. The excitons emit light when they transition from the excited state to the ground state. The injection and flow of holes and electrons should be balanced, so that OLEDs with the above structure have excellent efficiency and / or a long lifetime.

[0004] There remains a need to improve the performance of organic semiconductor materials, semiconductor layers, and their organic electronic devices, particularly by improving the properties of the compounds that constitute them, thereby achieving improved operating voltage, efficiency, lifetime, and / or long-term voltage stability. Furthermore, there remains a need to improve LUMO energy, dipole moment, and / or thermal properties compared to comparative examples, thereby improving thermal stability and / or processing characteristics at elevated temperatures. In particular, there is a demand for compounds for organic semiconductor materials that exhibit good volatility and thermal stability, which is useful for improving the manufacturing of OLED devices, for example.

[0005] (DISCLOSURE) One aspect provides a compound of formula (I):

[0006]

Chemical Formula

[0007] [In formula (I), A 1 is represented by formula (II),

[0008]

Chemical Formula

[0009] In formula (II), B 1 is represented by formula (III),

[0010]

Chemical Formula

[0011] wherein the asterisk "*" indicates a bonding site, X 1 is selected from CR 1 or N; X 2 is selected from CR 2 or N; X 3 is selected from CR 3 or N; X 4 is selected from CR 4 or N; X 5 is selected from CR 5 or N; R 1 , R 2 , R 3 , R 4 , and R 5 are each independently H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, optionally, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Selected from heteroaryls; and / or, X 1 , X 2 , X 3 , X 4, and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Selected from heteroaryls; Here, R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; and, Optionally, the following compounds E1 to E5:

[0012]

Chemical

[0013] are excluded.

[0014] Throughout the present application and the claims, unless otherwise specified, any A 1 , A 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R a , R b , R c , R d , X 1 , X 2 , X 3 , X 4 , X 5 and the like should be noted to always refer to the same moiety.

[0015] In the present specification, unless otherwise specifically defined, "partially fluorinated" refers to a C1-C8 alkyl group in which only part of the hydrogen atoms are substituted with fluorine atoms.

[0016] In the present specification, unless otherwise specifically defined, "perfluorinated" refers to a C1-C8 alkyl group in which all hydrogen atoms are substituted with fluorine atoms.

[0017] In the present application, for X 1 , X 2 , X 3 , X 4 , X 5 , substituted or unsubstituted C1-C6 aryl to C 40 aryl, substituted or unsubstituted C1-C3 heteroaryl to C 40 heteroaryl, wherein the "C-" atoms are each CR 1 , CR 2 , CR 3, CR 4 , CR 5 means representing the "C" atom, R 1 , R 2 , R 3 , R 4 , R 5 each represents a group selected from C6 aryl to C 40 aryl, C3 heteroaryl to C 40 heteroaryl, .

[0018] In the present application, substituted or unsubstituted C-C6 aryl to C-C 40 aryl means that C6 to C 40 aryl may be substituted or unsubstituted.

[0019] In the present application, substituted or unsubstituted C-C3 heteroaryl to C-C 40 heteroaryl means that C3 to C 40 heteroaryl may be substituted or unsubstituted.

[0020] In the present application, C m F 2m+1 (where m is 1 to 8) may be used synonymously with the term "perfluorinated C1-C8 alkyl".

[0021] In the present application, C m F (2m+1)-t H t (where m=1 to 8 and t=1 to 2m) may be used synonymously with the term "partially fluorinated C1-C8 alkyl".

[0022] In the present application, OC m F 2m+1 (where m is 1 to 8) may be used synonymously with the term "perfluorinated C1-C8 alkoxy".

[0023] In the present application, OC m F (2m+1)-t H tThe term (where m=1 to 8 and t=1 to 2m) may be used synonymously with the term "partially fluorinated C1-C8 alkoxy".

[0024] In this specification, unless otherwise defined, “substituted” means deuterium, C1-C 12 Alkyl and C1-C 12 This refers to substances that have been substituted with alkoxy.

[0025] However, in this specification, "aryl substitution" means substitution with one or more aryl groups, and the aryl group itself may be substituted with one or more aryl groups and / or heteroaryl groups.

[0026] Similarly, in this specification, "heteroaryl substitution" means substitution by one or more heteroaryl groups, and the heteroaryl group itself may be substituted by one or more aryl groups and / or heteroaryl groups.

[0027] In this specification, unless otherwise defined, "alkyl group" refers to a saturated aliphatic hydrocarbon group. Alkyl groups are C1-C 12 Alkyl groups may also be used. More specifically, alkyl groups are C1-C 10 It may be an alkyl group or a C1-C6 alkyl group. For example, a C1-C4 alkyl group has 1-4 carbon atoms in the alkyl chain and may be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl.

[0028] Specific examples of alkyl groups may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl groups.

[0029] The term "cycloalkyl" refers to a saturated hydrocarbon group derived from a cycloalkane, obtained by formally removing one hydrogen atom from the cyclic atom contained in the corresponding cycloalkane. Examples of cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and adamantyl groups.

[0030] The term "hetero" means that in a structure which may be formed by covalently bonded carbon atoms, at least one carbon atom is substituted by another polyvalent atom. Preferably, the heteroatom is selected from B, Si, N, P, O, and S; more preferably, it is selected from N, P, O, and S.

[0031] In this specification, “aryl group” means a hydrocarbon group that can be produced by formally removing one hydrogen atom from an aromatic ring in the corresponding aromatic hydrocarbon. An aromatic hydrocarbon means a hydrocarbon containing at least one aromatic ring or aromatic ring system. An aromatic ring or aromatic ring system means a planar ring or ring system of covalently bonded carbon atoms, which includes a conjugated system of delocalized electrons that satisfies Hückel’s rules. Examples of aryl groups include monocyclic groups (such as phenyl or tolyl), polycyclic groups containing multiple aromatic rings linked by single bonds (such as biphenyl), and polycyclic groups containing fused rings (such as naphthyl or fluoren-2-yl).

[0032] Similarly, a heteroaryl group is understood, in particular where appropriate, to be obtained by formally removing one ring hydrogen from a heterocyclic aromatic ring in a compound containing at least one such ring.

[0033] A heterocycloalkyl group is understood, in particular where appropriate, to be a group obtained by formally removing one ring hydrogen from a saturated cycloalkyl ring in a compound containing at least one such ring.

[0034] The term "fused aryl ring" or "condensed aryl ring" refers to a ring in which two aryl rings have at least two common sp² rings. 2 This means that when hybrid carbon atoms share a common set of atoms, they are considered to be fused or condensed.

[0035] The term "six-membered ring" is understood to mean a ring formed by six atoms. The atoms forming the "six-membered ring" may be bonded to additional atoms on the outside of the ring, such as hydrogen atoms.

[0036] The term "five-membered ring" is understood to mean a ring formed by five atoms. The atoms forming the "five-membered ring" may be bonded to additional atoms outside the ring, such as hydrogen atoms.

[0037] In this specification, a single bond refers to a direct bond.

[0038] The terms "free of," "does not contain," and "does not comprise" do not exclude impurities that may be present in the compound before deposition. These impurities have no technical effect on the objectives achieved by this invention.

[0039] The term "contacting and sandwiched" refers to a configuration of three layers in which the central layer is in direct contact with two adjacent layers.

[0040] The terms "light-absorbing layer" and "light absorption layer" are used synonymously.

[0041] The terms "light-emitting layer," "light emission layer," and "emission layer" are used synonymously.

[0042] The terms "p-type charge generation layer," "p-CGL," and "hole generation layer" are used synonymously.

[0043] The terms "n-type charge generation layer," "n-CGL," and "electron generation layer" are used synonymously.

[0044] The terms "OLED," "organic light-emitting diode," and "organic light-emitting device" are used synonymously.

[0045] The terms "anode," "anode layer," and "anode electrode" are used synonymously.

[0046] The terms "cathode," "cathode layer," and "cathode electrode" are used synonymously.

[0047] In this specification, hole properties refer to the ability to donate electrons and form holes when an electric field is applied, and holes formed at the anode may be easily injected into the light-emitting layer or transported within the light-emitting layer due to the conductive properties based on the highest occupied molecular orbital (HOMO) level.

[0048] Furthermore, electronic properties refer to the ability to accept electrons when an electric field is applied. Electrons formed in the cathode may be easily injected into the light-emitting layer or transported within the light-emitting layer due to conductive properties based on the lowest unoccupied molecular orbital (LUMO) level.

[0049] [Exclusion I] According to one embodiment, compounds having at least one unsubstituted aromatic six-membered ring are excluded.

[0050] According to one embodiment, compounds having at least two unsubstituted aromatic six-membered rings are excluded.

[0051] According to one embodiment, compounds having a Cl substituent are excluded.

[0052] According to one embodiment, compounds having at least one Cl substituent are excluded.

[0053] According to one embodiment, compounds having at least two Cl substituents are excluded.

[0054] According to one embodiment, compounds having at least three Cl substituents are excluded.

[0055] According to one embodiment, compounds having more than one CN substituent, at least one Cl substituent, and no F substituent are excluded.

[0056] According to one embodiment, compounds having one or more CN substituents, at least two Cl substituents, and no F substituents are excluded.

[0057] According to one embodiment, compounds having one or more CN substituents, at least three Cl substituents, and no F substituents are excluded.

[0058] According to one embodiment, compounds having more than two CN substituents, at least one Cl substituent, and no F substituent are excluded.

[0059] According to one embodiment, compounds having more than two CN substituents, at least two Cl substituents, and no F substituents are excluded.

[0060] According to one embodiment, compounds having more than two CN substituents, at least three Cl substituents, and no F substituents are excluded.

[0061] According to one embodiment, compounds having more than three CN substituents, at least one Cl substituent, and no F substituent are excluded.

[0062] According to one embodiment, compounds having more than three CN substituents, at least two Cl substituents, and no F substituents are excluded.

[0063] According to one embodiment, compounds having more than three CN substituents, at least three Cl substituents, and no F substituents are excluded.

[0064] According to one embodiment, compounds having more electron-withdrawing groups other than CN groups than CN groups are excluded.

[0065] According to one embodiment, compounds having more than 10 CN substituents are excluded.

[0066] According to one embodiment, compounds having more than 10 CN substituents and at least one Cl substituent are excluded.

[0067] According to one embodiment, compounds having more than six CN substituents and more than six groups selected from halogen atoms and / or halogen-substituted alkyl groups are excluded.

[0068] According to one embodiment, compounds having more than nine CN substituents and more than six groups selected from halogen atoms and / or halogen-substituted alkyl groups are excluded.

[0069] According to one embodiment, compounds having more than six CN substituents and more than three halogen-substituted alkyl groups are excluded.

[0070] According to one embodiment, compounds having more than nine CN substituents and more than three halogen-substituted alkyl groups are excluded.

[0071] According to one embodiment, R a , R b , R c ~R d It does not contain halogens.

[0072] [Exclusion II] According to one embodiment, the compound of formula (I) is represented as follows:

[0073] [ka]

[0074] [In formula (I), A 1 This is expressed by equation (II),

[0075] [ka]

[0076] In formula (II), B 1 It is expressed by equation (III),

[0077] [ka]

[0078] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; and / or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R dAt least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; and, Optionally, the following compounds E1-E5:

[0079] [ka]

[0080] [This is excluded.]

[0081] According to one embodiment, the compound of formula (I) is represented as follows:

[0082] [ka]

[0083] [In formula (I), A 1 This is expressed by equation (II),

[0084] [ka]

[0085] In formula (II), B 1 It is expressed by equation (III),

[0086] [ka]

[0087] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COCm F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; and, Optionally, the following compounds E1-E5:

[0088] [ka]

[0089] [This is excluded.]

[0090] According to one embodiment, the compound of formula (I) is excluded, and the groups E1 to E5:

[0091] [ka]

[0092] Selected from.

[0093] According to one embodiment, the compound of formula (I) is excluded, where, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, Preferably, selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl, or fully fluorinated C1-C8 alkyl; X 1 , X 2 , X 3 , X 4 , and, X 5 At least two of are independently selected from CH, CD, or N; and, Here, R a and R d is selected from F, and R b and R c is selected from F or CN; or, R a and R d is selected from F, and R b and R c is selected from CN; or, R a and R d is selected from F, and R b and R c is selected from F; or, R a and R d is selected from F or CN, and R b and R c is selected from F; or, R a and R d is selected from CN, and R b and R c is selected from F; and, Optionally, the following compounds E1-E5:

[0094] [ka]

[0095] It will be excluded.

[0096] According to one embodiment, the compound of formula (I) is excluded, where, R 1, R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, Preferably, selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl, or fully fluorinated C1-C8 alkyl; X 1 , X 2 , X 3 , X 4 , and, X 5 At least two of are independently selected from CH, CD, or N; and, Here, R a and R d is selected from F, and R b and R c is selected from F or CN; or, R a and R d is selected from F, and R b and R c is selected from CN; or, R a and R d is selected from F, and R b and R c is selected from F; or, R a and R d is selected from F or CN, and R b and R c is selected from F; or, R a and R d is selected from CN, and R b and R c is selected from F; and / or, Optionally, the following compounds E1-E5:

[0097] [ka]

[0098] is excluded; and / or, Optionally, R 1 , R 2 , R 3 , R 4 , and, R 5 Those that are halogens are excluded.

[0099] According to one embodiment, the compound of formula (I) is excluded, where, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, Preferably, selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl, or fully fluorinated C1-C8 alkyl; X 1 , X 2 , X 3 , X 4 , and, X 5 At least two of are independently selected from CH, CD, or N; and, Here, R a and R d is selected from F, and R b and R c is selected from F or CN; or, R a and R d is selected from F, and R b and R c is selected from CN; or, R a and R d is selected from F, and R b and R c is selected from F; or, R a and R dis selected from F or CN, and R b and R c is selected from F; or, R a and R d is selected from CN, and R b and R c is selected from F; and, The following compounds E1-E5:

[0100] [ka]

[0101] and, R 1 , R 2 , R 3 , R 4 , and, R 5 Those that are halogens are excluded.

[0102] According to one embodiment, the compound of formula (I) is excluded, where, R 1 , R 2 , R 3 , R 4 , and, R 5 It is a halogen.

[0103] According to one embodiment, the compound of formula (I) is excluded, where, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl, or fully fluorinated C1-C8 alkyl; X 1 , X 2 , X 3 , X 4 , and, X 5 At least two of are independently selected from CH, CD, or N; and, R a, R b , R c , R d These two are independently selected from F or CN, and R a , R b , R c , R d The remaining two are selected from F.

[0104] According to one embodiment, the compound of formula (I) is excluded, where, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl, or fully fluorinated C1-C8 alkyl; X 1 , X 2 , X 3 , X 4 , and, X 5 At least two of are independently selected from CH, CD, or N; and, R a , R b , R c , R d These two are independently selected from F, Cl, CN, or CF3, preferably selected from F or CN.

[0105] According to one embodiment, the compound of formula (I) is excluded, where, R a and R d is selected from F, and R b and R c is selected from F or CN; or, R a and R d is selected from F, and R b and R c is selected from CN; or, R a and R d is selected from F, and R b and R cis selected from F; or, R a and R d is selected from F or CN, and R b and R c is selected from F; or, R a and R d is selected from CN, and R b and R c It is selected from F.

[0106] According to one embodiment, the compound of formula (I) is excluded, where, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, F, Cl, CN, CF3, selected from partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl; and here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is independently selected from CH, CD, or N; and here, R a and R d is selected from F, and R b and R c is selected from F or CN; or, R a and R d is selected from F, and R b and R c is selected from CN; or, R a and R d is selected from F, and R b and R c is selected from F; or, R a and R d is selected from F or CN, and R b and R cis selected from F; or, R a and R d is selected from CN, and R b and R c It is selected from F.

[0107] According to one embodiment, the compound of formula (I) is excluded, where, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is independently selected from CH, CD, or N; and here, R a , R b , R c , R d These two are independently selected from F or CN, and the remaining two R a , R b , R c , R d It is selected from F.

[0108] According to one embodiment, the compound of formula (I) is excluded, where, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, F, Cl, CN, CF3, selected from partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl; and here, X 1 , X 2 , X 3 , X 4 , and, X 5At least one of is independently selected from CH, CD, or N; and here, R a , R b , R c , R d It is independently selected from F or CN.

[0109] According to one embodiment, the compound of formula (I) is excluded, where, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, F, Cl, CN, CF3, selected from partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl; and here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is independently selected from CH, CD, or N; and, R a , R b , R c , R d This is independently selected from F, Cl, CN, or CF3.

[0110] According to one embodiment, the compound of formula (I) is excluded, where, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, F, Cl, CN, CF3, selected from partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl; and here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least two of are independently selected from CH, CD, or N; and, R a , R b , R c , and, R d This is independently selected from F, Cl, CN, or CF3.

[0111] According to one embodiment, the compound of formula (I) is excluded, where, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl; and, X 1 , X 2 , X 3 , X 4 , and, X 5 At least two of are independently selected from CH, CD, or N; and here, R a , R b , R c , R d It is independently selected from F or CN.

[0112] According to one embodiment, sp 2 Compounds having more than four halogens directly bonded to the hybrid carbon atoms are excluded.

[0113] According to one embodiment, sp 2 Compounds having more than three halogens directly bonded to the hybrid carbon atoms are excluded.

[0114] According to one embodiment, sp 2 Compounds having more than two halogens directly bonded to the hybrid carbon atoms are excluded.

[0115] According to one embodiment, sp 2 Compounds having more than one halogen directly bonded to the hybrid carbon atoms are excluded.

[0116] According to one embodiment of formula (I), the sp of halogen 2 Direct bonding to hybrid carbon atoms is excluded.

[0117] According to one embodiment, the compound of formula (I) is sp 2 It does not contain F or Cl that are directly bonded to the hybrid carbon atoms.

[0118] [Advantageous effects] Surprisingly, it was found that the organic compound according to formula (I) solves the underlying problem of the present invention by enabling devices that are superior in various aspects to organic electroluminescent devices known in the art, particularly in terms of operating voltage, efficiency, and / or lifetime, and especially in terms of operating voltage, efficiency, and long-term voltage stability. Even more surprisingly, it was found that the compound according to formula (I) may improve LUMO energy, dipole moment, and / or thermal properties, and particularly thermal stability and / or workability at high temperatures, compared to comparative examples.

[0119] Surprisingly, it was found that the organic compound according to formula (I) possesses both sufficiently low volatility and high volatility that adequately limits the thermal stress during vapor deposition necessary for mass production.

[0120] Surprisingly, it was found that the LUMO energy of the organic compound according to equation (I) falls within the range required for efficient hole injection and charge generation.

[0121] In particular, and surprisingly, the quinoid compound of formula (I) was found to exhibit good thermal stability and characteristics suitable for the fabrication of organic light-emitting diodes under thermal deposition conditions. Furthermore, these compounds exhibit extremely negative LUMO energy levels. These compounds enable good OLED performance, such as low operating voltage, and also enable high stability of organic electronic devices, such as voltage rise over time and lifetime.

[0122] The compounds described above may be used as dopants in the hole injection layer and / or p-type charge generation layer of an organic light-emitting device.

[0123] The suitability of the compound of formula (I) is particularly for the fabrication of OLED devices under thermal deposition conditions, especially for compounds that do not contain ArC-F bonds (sp 2 Further improvements can be made if there are no direct F or Cl bonds in the carbon atoms. In this case, the voltage rise over time in organic electronic devices, particularly those including a p-type charge generation layer, may be further reduced. Compounds of formula (I) are particularly suitable for OLED device manufacturing under thermal deposition conditions when two to three cyano groups (CN groups) are used as substituents Ra, Rb, Rc, and Rd on the quinone skeleton. In particular, when two CN groups are used as substituents, a low operating voltage and excellent stability (especially moisture resistance) are obtained. In one embodiment of compound (I), two or three of the Ra, Rb, Rc, and Rd of the quinone skeleton are CN groups. The suitability of the compound of formula (I) for the manufacture of OLED devices under thermal deposition conditions is particularly evident in R a , R a , R b , R c , and, R d It can be further improved when 2-3 CN groups are used in the quinone skeleton. In particular, R a , R a , R b , R c , and, R d The two CN groups present in the quinone skeleton provide low operating voltage and high stability, especially against moisture. In one embodiment of the compound of formula (I), the R of the quinone skeleton a , R b , R c , and, R d It contains 2 to 3 CN groups. Having 6 to 9 CN groups throughout the molecule improves the volatility of the compound of formula (I), and this volatility is particularly suitable for the production of OLEDs under thermal deposition conditions. The amount of CN groups in the compound of formula (I) affects the desired LUMO energy level, such as ≤ -4.95 eV, which improves the operating voltage of an OLED, for example.

[0124] [Compounds of formula (I)] According to one embodiment, the compound of formula (I) is represented as follows:

[0125] [ka]

[0126] [In formula (I), A 1 This is expressed by equation (II),

[0127] [ka]

[0128] In formula (II), B 1 It is expressed by equation (III),

[0129] [ka]

[0130] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, SF5, Selected from the group including; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; or, X 1, X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; and, The following compounds E1-E5:

[0131] [ka]

[0132] [This is excluded.]

[0133] According to one embodiment, the compound of formula (I) is represented as follows:

[0134] [ka]

[0135] [In formula (I), A 1 This is expressed by equation (II),

[0136] [ka]

[0137] In formula (II), B 1 It is expressed by equation (III),

[0138] [ka]

[0139] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COCm F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, Ra , R b , R c ~R d At least one or at least two of are independently selected from H or D, Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; and, The following compounds E1-E5:

[0140] [ka]

[0141] [This is excluded.]

[0142] According to one embodiment, a compound of formula (I):

[0143] [ka]

[0144] [In formula (I), A 1 This is expressed by equation (II),

[0145] [ka]

[0146] In formula (II), B 1 It is expressed by equation (III),

[0147] [ka]

[0148] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, R a , Rb , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, the compound of formula (I) is excluded, and here, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, Preferably, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, Selected from the group including; X 1 , X 2 , X 3 , X 4 , and, X 5 At least two of are independently selected from CH, CD, or N; and, Here, R a and R d is selected from F, and R b and R c is selected from F or CN; or, R a and Rd is selected from F, and R b and R c is selected from CN; or, R a and R d is selected from F, and R b and R c is selected from F; or, R a and R d is selected from F or CN, and R b and R c is selected from F; or, R a and R d is selected from CN, and R b and R c is selected from F; and, Here, the following compounds E1-E5:

[0149] [ka]

[0150] [This is excluded.]

[0151] According to one embodiment, a compound of formula (I):

[0152] [ka]

[0153] [In formula (I), A 1 This is expressed by equation (II),

[0154] [ka]

[0155] In formula (II), B 1 It is expressed by equation (III),

[0156] [ka]

[0157] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, the compound of formula (I) is excluded, and here, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl, or fully fluorinated C1-C8 alkyl; X 1 , X 2 , X 3 , X 4 , and, X 5 At least two of are independently selected from CH, CD, or N; and, R a , R b , R c , R d These two are independently selected from F or CN, and R a , R b , R c , R d The remaining two are selected from F; and, Here, the following compounds E1-E5:

[0158] [ka]

[0159] [This is excluded.]

[0160] According to one embodiment, a compound of formula (I):

[0161] [ka]

[0162] [In formula (I), A 1 This is expressed by equation (II),

[0163] [ka]

[0164] In formula (II), B 1 It is expressed by equation (III),

[0165] [ka]

[0166] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R1 , R 2 , R 3 , R 4 , and R 5 are each independently H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 aryl, substituted or unsubstituted C3-C 40 heteroaryl, and SF5; wherein R 1 , R 2 , R 3 , R 4 , and R 5 the one or more substituents on the above are each independently selected from the group consisting of D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; wherein, X 1 , X 2 , X 3 , X 4 , and X 5 at least one, at least two, or at least three of which are each independently CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (wherein m is 1 to 8), or CC m F (2m+1)-t H t (wherein m=1 to 8 and t=1 to 2m), COCF3, COC m F 2m+1 (wherein m is 1 to 8), or COC m F (2m+1)-t H t (wherein m=1 to 8 and t=1 to 2m), substituted or unsubstituted C-C6 aryl to C-C 40 aryl, substituted or unsubstituted C-C3 heteroaryl to C-C 40Heteroaryl, Selected from; or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, the compound of formula (I) is excluded, and here, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl, or fully fluorinated C1-C8 alkyl; X 1 , X 2 , X 3 , X 4 , and, X 5 At least two of are independently selected from CH, CD, or N; and, R a , R b , R c , R d These two are independently selected from F, Cl, CN, or CF3, preferably selected from F or CN; and, Here, the following compounds E1-E5:

[0167] [ka]

[0168] [This is excluded.]

[0169] According to one embodiment, a compound of formula (I):

[0170] [ka]

[0171] [In formula (I), A 1 This is expressed by equation (II),

[0172]

Chem.

[0173] In formula (II), B 1 is represented by formula (III),

[0174]

Chem.

[0175] Here, the asterisk "*" indicates the bonding position, X¹ 1 is selected from CR¹ 1 or N; X² 2 is selected from CR² 2 or N; X³ 3 is selected from CR³ 3 or N; X⁴ 4 is selected from CR⁴ 4 or N; X⁵ 5 is selected from CR⁵ 5 or N; R¹ 1 , R² 2 , R³ 3 , R⁴ 4 , and R⁵ 5 are independently selected from the group consisting of H, D, F, Cl, CN, CF₃, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 aryl, substituted or unsubstituted C3-C 40 heteroaryl, and SF₅, wherein one or more substituents on R¹ 1 , R² 2 , R³ 3 , R⁴ 4 , and R⁵ 5 are independently Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COCm F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, the compound of formula (I) is excluded, and here, R a and R d is selected from F, and R b and R c is selected from F or CN; or, R a and R d is selected from F, and R b and R c is selected from CN; or, R a and R d is selected from F, and R b and Rc is selected from F; or, R a and R d is selected from F or CN, and R b and R c is selected from F; or, R a and R d is selected from CN, and R b and R c is selected from F; and, Here, the following compounds E1-E5:

[0176] [ka]

[0177] [This is excluded.]

[0178] According to one embodiment, a compound of formula (I):

[0179] [ka]

[0180] [In formula (I), A 1 This is expressed by equation (II),

[0181] [ka]

[0182] In formula (II), B 1 It is expressed by equation (III),

[0183] [ka]

[0184] Here, the asterisk "*" indicates the bond position. X 1 CR 1or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F(2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, the compound of formula (I) is excluded, and here, R a , R b , R c , R d At least one or at least two of are selected from H or D; and, Here, the following compounds E1-E5:

[0185] [ka]

[0186] [This is excluded.]

[0187] According to one embodiment, a compound of formula (I):

[0188] [ka]

[0189] [In formula (I), A 1 This is expressed by equation (II),

[0190] [ka]

[0191] In formula (II), B 1 It is expressed by equation (III),

[0192] [ka]

[0193] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COCm F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, the compound of formula (I) is excluded, and here, R a , R b , R c , R d At least one or at least two of are selected from H or D, and R is not selected from H or D. a , R b , R c , R d is selected from CN; and, Here, the following compounds E1-E5:

[0194] [ka]

[0195] [This is excluded.]

[0196] According to one embodiment, a compound of formula (I):

[0197] [ka]

[0198] [In formula (I), A 1 This is expressed by equation (II),

[0199] [ka]

[0200] In formula (II), B 1 It is expressed by equation (III),

[0201] [ka]

[0202] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; or, X 1 , X 2 , X 3 , X4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, the compound of formula (I) comprises at least 4 CN groups, preferably 4 to 10 CN groups, more preferably 4 to 9 CN groups, in addition preferably 5 to 9 CN groups, and more preferably 6 to 9 CN groups; and, Here, the following compounds E1-E5:

[0203] [ka]

[0204] [This is excluded.]

[0205] According to one embodiment, the compound of formula (I) comprises at least four CN groups and less than nine CN groups, preferably at least five CN groups and less than eight CN groups.

[0206] According to one embodiment, the compound of formula (I) contains ≥6 and ≤24 F groups, preferably ≥8 and ≤18 F groups. According to one embodiment, the R in the compound of formula (I) a , R b , R c ~R d At least one or at least two of them are H or D.

[0207] [Compounds of formula (IVa) or (IVb)] According to one embodiment, the compound of formula (I) is formula (IVa) or formula (IVb):

[0208] [ka]

[0209] or

[0210] [ka]

[0211] It is represented as follows.

[0212] According to one embodiment, the compound of formula (I) is formula (IVa) or formula (IVb):

[0213] [ka]

[0214] or

[0215] [ka]

[0216] It is represented as, In the formula, B 1 It is expressed by equation (III),

[0217] [ka]

[0218] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, electron-withdrawing group, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from D, electron-withdrawing group, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COCm F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; R a , R b , R c ~R d Independently, Selected from H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of the following: Selected from F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5.

[0219] According to one embodiment, the compound of formula (I) is formula (IVa) or formula (IVb):

[0220] [ka]

[0221] or

[0222] [ka]

[0223] It is represented as, In the formula, B 1 It is expressed by equation (III),

[0224] [ka]

[0225] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, electron-withdrawing group, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from D, electron-withdrawing group, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COCm F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; R a , R b , R c ~R d Independently, Selected from H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of the following: Selected from F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, SF5; and, Here, R a , R b , R c , and, R d At least one of them is selected from H or D.

[0226] According to one embodiment, the compound of formula (I) is formula (IVa) or formula (IVb):

[0227] [ka]

[0228] or

[0229] [ka]

[0230] It is represented as, In the formula, B 1 It is expressed by equation (III),

[0231] [ka]

[0232] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, electron-withdrawing group, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from D, electron-withdrawing group, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R 1 , R 2 , R 3 , R 4 , and, R 5 At least one, at least two, or at least three of these are independent of each other. F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from heteroaryls, SF5; R a , R b , R c ~R d Independently, Selected from H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of the following: Selected from F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, SF5; and, Herein, compositions containing the following compounds are excluded: R 1 , R 2 , R 3 , R 4 , and, R 5Independently, Selected from H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl; and, X 1 , X 2 , X 3 , X 4 , and, X 5 At least two of are independently selected from CH, CD, or N; and, Here, R a and R d is selected from F, and R b and R c is selected from F or CN; or, R a and R d is selected from F, and R b and R c is selected from CN; or, R a and R d is selected from F, and R b and R c is selected from F; or, R a and R d is selected from F or CN, and R b and R c is selected from F; or, R a and R d is selected from CN, and R b and R c It is selected from F.

[0233] According to one embodiment, the compound of formula (I) is formula (IVa) or formula (IVb):

[0234] [ka]

[0235] or

[0236] [ka]

[0237] It is represented as, In the formula, B 1 It is expressed by equation (III),

[0238] [ka]

[0239] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, electron-withdrawing group, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from D, electron-withdrawing group, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R 1 , R 2 , R 3 , R 4 , and, R 5 At least one, at least two, or at least three of these are independent of each other. F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from heteroaryls, SF5; R a , R b , R c ~R d Independently, Selected from H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of the following: Selected from F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, SF5; and, Herein, compositions containing the following compounds are excluded: R 1 , R 2 , R 3 , R 4 , and, R 5Independently, Selected from H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl; and, X 1 , X 2 , X 3 , X 4 , and, X 5 At least two of are independently selected from CH, CD, or N; and, Here, R a and R d is selected from F, and R b and R c is selected from F or CN; or, R a and R d is selected from F, and R b and R c is selected from CN; or, R a and R d is selected from F, and R b and R c is selected from F; or, R a and R d is selected from F or CN, and R b and R c is selected from F; or, R a and R d is selected from CN, and R b and R c is selected from F; and, Furthermore, the following compounds E1-E5:

[0240] [ka]

[0241] It will be excluded.

[0242] [Compounds of formulas (VA)~(VH) and (VJ)~(VR)] According to one embodiment, the compounds of formula (I) are (VA)~(VH) and (VJ)~(VR):

[0243] [ka]

[0244] It is represented as follows.

[0245] According to a preferred embodiment, the compound of formula (I) is selected from formulas (VA) to (VH) and (VJ) to (VN). This may further improve the operating voltage of the organic electronic device.

[0246] In a more preferred embodiment, the compound is represented by formula (VA) or (VM).

[0247] This may further improve the stability of the compound, particularly against moisture.

[0248] According to a more preferred embodiment, the compound of formula (I) is selected from formulas (VA) to (VH).

[0249] According to the most preferred embodiment, the compound is represented by formula (VA) or (VD).

[0250] For compounds (VA)~(VH) and (VJ)~(VR), their stability against moisture may be further improved.

[0251] According to one embodiment, the compounds of formula (I), (IVa), (IVb), (VA)~(VH), and (VJ)~(VR) contain at least 4 CN groups, preferably up to 10 CN groups, more preferably 4 to 9 CN groups, even more preferably 5 to 9 CN groups, even more preferably 6 to 8 CN groups, even more preferably 5 to 7 CN groups, in addition preferably 5 to 9 CN groups, and more preferably 6 to 9 CN groups. According to one embodiment, the compounds of formula (I), (IVa), (IVb), (VA)~(VH), and (VJ)~(VR) contain at least 6 CN groups. According to one embodiment, the compounds of formula (I), (IVa), (IVb), (VA)~(VH), and (VJ)~(VR) contain 4 to 10 CN groups. According to a preferred embodiment, the compounds of formula (I), (IVa), (IVb), (VA)~(VH), and (VJ)~(VR) contain 4 to 9 CN groups. According to a more preferred embodiment, the compounds of formula (I), (IVa), (IVb), (VA)~(VH), and (VJ)~(VR) contain 5 to 9 CN groups. According to the most preferred embodiment, the compounds of formula (I), (IVa), (IVb), (VA)~(VH), and (VJ)~(VR) contain 6 to 9 CN groups.

[0252] A certain amount of CN groups may be used to ensure the volatility of the compound of formula (I), which is particularly suitable for the production of OLEDs under thermal deposition conditions. Limiting the amount of CN groups to a certain range can further improve the suitability of the compound of formula (I) for the production of OLED devices under heat treatment / vacuum treatment. Furthermore, when 6 to 9 CN groups are used in particular, thermal stability can be further improved, i.e., the decomposition temperature can be further increased.

[0253] [R a , R b , R c , and, R d ] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5.

[0254] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c ~R d Independently, Selected from the group comprising H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of the following: Selected from CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5.

[0255] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , Rb , R c ~R d Independently, Selected from the group comprising H, D, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of the following: Selected from CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5.

[0256] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c ~R d Independently, Selected from the group comprising H, D, CN, CF3, partially fluorinated C1-C8 alkyl groups, or fully fluorinated C1-C8 alkyl groups; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of the following: Selected from CN, CF3, partially fluorinated C1-C8 alkyl groups, or fully fluorinated C1-C8 alkyl groups.

[0257] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c ~R d Independently, The group is selected from those including H, D, F, CN, and CF3.

[0258] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c ~R d Independently, Selected from the group including H, D, F, CN, and CF3, Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. The group is selected from those including F, CN, and CF3.

[0259] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c ~R d Independently, The group is selected from the group including H, D, F, and CN.

[0260] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c ~R d Independently, Selected from the group including H, D, F, and CN, Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. The group is selected from those including CN and CF3.

[0261] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c ~Rd Independently, Selected from the group including H, D, and CN, Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independently selected from the group that includes CN.

[0262] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c ~R d Independently, The group is selected from the group containing H, D, and CN.

[0263] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c ~R d It is selected from CN.

[0264] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c ~R d Independently, Selected from the group including H, D, and CN, Here, R a , R b , R c ~R d One or two of are independently selected from H or D, and R a , R b , R c ~R d Two to three of these will be selected from the CN.

[0265] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c ~R d Independently, Selected from the group including H, D, and CN, Here, R a , R b , R c ~R d The two are independently selected from H or D, and R a , R b , R c ~R d These two are selected from CN.

[0266] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c ~R d Independently, Selected from the group including H, D, and CN, Here, R a , R b , R c ~R d One of them is independently selected from H or D, and R a , R b , R c ~R d These three are selected from CN.

[0267] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c ~R d Independently, Selected from the group including H, D, and CN, Here, R a , R b , R c ~R d The two are independently selected from H or D, and Ra , R b , R c ~R d These two are selected from CN.

[0268] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a and R d is independently selected from H or D, and R b and R c It is independently selected from H, D, or CN; or, R a and R d is independently selected from H or D, and R b and R c It is independently selected from CN; or, R a and R d is independently selected from H, D, or CN, and R b and R c is independently selected from H or D; or, R a and R d is selected from CN, and R b and R c It is independently selected from H or D.

[0269] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a and R d is independently selected from H or D, and R b and R c R is independently selected from H, D, or CN. According to one embodiment, in compounds of formula (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a and R d is independently selected from H or D, and R b and R cR is independently selected from CN. According to one embodiment, in compounds of formula (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a and R d is independently selected from H, D, or CN, and R b and R c R is selected from H or D. According to one embodiment, in compounds of formula (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a and R d is selected from CN, and R b and R c It is independently selected from H or D.

[0270] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a and R d Two of these are independently selected from H, D, or CN, and the remaining two R a , R b , R c , R d R is independently selected from H or D. According to one embodiment, in compounds of formula (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c , R d R is independently selected from H, D, or CN. According to one embodiment, in compounds of formula (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c , R d It is independently selected from H, D, CN, or CF3.

[0271] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c, and, R d At least one or at least two of are independently selected from H or D; or R a , R b , R c , and, R d All of these are selected from CN.

[0272] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c , and, R d At least one or at least two of are independently selected from H or D.

[0273] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c , and, R d At least one of them is selected from CN.

[0274] According to one embodiment, in compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), R a , R b , R c , and, R d At least two of these are selected from CN.

[0275] According to one embodiment, R a , R b , R c , and, R d If R a , R b , R c , and, R d Independently, Selected from H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, or SF5; or Here, R a , R b , R c , and, R d At least one, at least two, or at least three of the following: Selected from CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, or SF5.

[0276] According to one embodiment, R a , R b , R c , and, R d If R a , R b , R c , and, R d Independently, Selected from H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5, but not selected from halogens.

[0277] According to one embodiment, R a , R b , R c , and, R d If R a , R b , R c , and, R d Independently, Selected from H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, SF5, and not selected from halogens.

[0278] This may further reduce the voltage rise over time in organic electronic devices, particularly those including a p-type charge generation layer.

[0279] According to a preferred embodiment, R a , R b , R c , and, R d If R a , R b , R c , and, R d Independently, Selected from H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, or SF5. Here, R a , R b , R c , and, R d If R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, or SF5.

[0280] This may further reduce the voltage rise over time in organic electronic devices, particularly those including a p-type charge generation layer.

[0281] According to a more preferred embodiment, R a , R b , R c , and, R d If R a , R b , R c , and, R d Independently, Selected from H, D, CN, CF3, or SF5; Here, R a , R b , R c , and, R d If Ra , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Select from CN, CF3, or SF5.

[0282] Furthermore, according to a more preferred embodiment, R a , R b , R c , and, R d If R a , R b , R c , and, R d Independently, Select from H, D, CN, or CF3. Here, R a , R b , R c , and, R d If R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from CN or CF3. This may further reduce the voltage rise of the organic electronic device over time, and may also further reduce the operating voltage.

[0283] According to the most preferred embodiment, R a , R b , R c , and, R d If R a , R b , R c , and, R d Independently, Selected from H, D, and CN; Here, R a , R b , R c , and, R d If R a , R b , R c , and, Rd At least one, at least two, or at least three of the CNs are selected.

[0284] As a result, in organic electronic devices containing compounds of formula (I), (IVa), (IVb), (Va) to (VR), particularly in p-type charge generation layers containing compounds of formula (I), (IVa), (IVb), (Va) to (VR), the voltage rise over time may be further reduced.

[0285] According to one embodiment, in equations (I), (IVa), (IVb), (Va)~(VR), R a , R b , R c , and, R d If R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5.

[0286] Therefore, R a , R b , R c , and, R d If R a , R b , R c , and, R d 1 to 4 of them, or 2 to 4 of them, or 2 to 3 of them, or 2 of them Selected from CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5.

[0287] Therefore, R a , R b , R c , and, R dOne to four, two to four, two to three, or two of these will be selected from CN.

[0288] The operating voltage of organic electronic devices containing compounds of formulas (I), (IVa), (IVb), (Va)~(VR) may be further improved. Furthermore, R a , R b , R c , and, R d If two or three, or two, of these are selected from CN, the stability of the compound, especially against moisture, may be further improved. a , R b , R c , and, R d If two of these are selected from CN, the stability of the compound, especially against moisture, may be further improved.

[0289] [R of equations (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR)] 1 , R 2 , R 3 , R 4 , and, R 5 ] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5.

[0290] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5.

[0291] According to one embodiment, in equations (I), (IVa), (IVb), (Va)~(VR), R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40Selected from heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5.

[0292] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, Preferably, the group is selected from F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl, or fully fluorinated C1-C8 alkyl.

[0293] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from the group comprising F, Cl, CN, CF3, and partially fluorinated or fully fluorinated C1-C8 alkyl groups.

[0294] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 , R 2 , R 3 , R 4, and, R 5 Independently, Selected from the group comprising F, CN, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, or SF5.

[0295] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from the group comprising F, Cl, CN, CF3, and partially fluorinated or fully fluorinated C1-C8 alkyl groups.

[0296] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from the group containing F, Cl, CN, or CF3, Preferably, it is selected from F or CN.

[0297] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from the group including H, D, F, Cl, CN, and CF3, the halogen is sp 2 It is assumed that it is not directly bonded to carbon. Furthermore, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C40 Aryl, substituted or unsubstituted C3-C 40 Selected from heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl, fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5.

[0298] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from the group including H, D, CN, and CF3, where the halogen is sp 2 It is assumed that it is not directly bonded to carbon. Furthermore, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from D, CN, CF3, partially fluorinated C1-C8 alkyl groups, fully fluorinated C1-C8 alkyl groups, or SF5.

[0299] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 , R 2, R 3 , R 4 , and, R 5 Independently, Selected from the group including H, D, F, Cl, CN, and CF3, the halogen is sp 2 It is assumed that it is not directly bonded to carbon. Furthermore, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, preferably selected from F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl, or fully fluorinated C1-C8 alkyl.

[0300] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from the group including F, Cl, CN, and CF3, and the halogen is sp 2 It is assumed that it is not directly bonded to carbon. Furthermore, it is selected from partially fluorinated C1-C8 alkyl groups or fully fluorinated C1-C8 alkyl groups.

[0301] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, A group including F is selected, and the halogen is sp 2 It is assumed that it is not directly bonded to carbon. Furthermore, the selection is made from partially fluorinated C1-C8 alkyl groups, fully fluorinated C1-C8 alkyl groups, or SF5.

[0302] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from the group including F, Cl, CN, and CF3, and the halogen is sp 2 It is assumed that it is not directly bonded to carbon. Furthermore, it is selected from partially fluorinated C1-C8 alkyl groups or fully fluorinated C1-C8 alkyl groups.

[0303] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from the group including F, Cl, CN, or CF3, and the halogen is sp 2 It is assumed that it is not directly bonded to carbon. Preferably, selected from F or CN, provided that the halogen is sp 2 Assume that it is not directly bonded to carbon.

[0304] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 and R 3 is selected from F, and R 2 and R 5 is selected from F or CN, and R 4 is selected from H or D; or R 1 and R 2 is selected from F, and R 4 and R 3 is selected from CN, and R 3 is selected from H or D; or R 1 and R 3 is selected from F, and R 4 and R 5 is selected from F, and R 2is selected from H or D; or R 2 and R 3 is selected from F or CN, and R 4 and R 5 is selected from F, and R 1 It is selected from H or D.

[0305] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 and R 2 It is selected from CF3, and R 3 and R 5 is selected from CF3 or CN, and R 4 is selected from H or D; or R 1 and R 2 It is selected from CF3, and R 4 and R 5 is selected from CN, and R 3 is selected from H or D; or R 1 and R 3 It is selected from CF3, and R 4 and R 5 It is selected from CF3, and R 2 is selected from H or D; or R 2 and R 3 is selected from CF3 or CN, and R 4 and R 5 It is selected from CF3, and R 1 It is selected from H or D.

[0306] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 and R 2 is selected from F, and R 3 and R 5 is selected from F or CN, and R 4 is selected from H or D; or R 1 and R 2 is selected from F, and R4 and R 5 is selected from CN, and R 3 is selected from H or D; or R 1 and R 3 is selected from F, and R 4 and R 5 is selected from F, and R 2 is selected from H or D; or R 2 and R 3 is selected from F or CN, and R 4 and R 5 is selected from F, and R 1 It is selected from H or D.

[0307] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), where R 1 and R 2 is selected from CF3, and R 3 and R 5 is selected from CF3 or CN, and R 4 is selected from H or D; or R 1 and R 2 is selected from CF3, and R 4 and R 5 is selected from CN, and R 3 is selected from H or D; or R 1 and R 3 is selected from CF3, and R 4 and R 5 is selected from CF3, and R 2 is selected from H or D; or R 2 and R 3 is selected from CF3 or CN, and R 4 and R 5 is selected from CF3, and R 1 It is selected from H or D.

[0308] [X in equations (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR)] 1 , X2 , X 3 , X 4 , and, X 5 ] According to one embodiment of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (where m=1 to 8 and t=0 to 2m is selected; or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t It is selected from (where t = 0 to 2m).

[0309] According to one embodiment, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, substituted or unsubstituted C6-C40 Aryl, substituted or unsubstituted C3-C 40 Selected from heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from D, CN, CF3, partially fluorinated C1-C8 alkyl, fully fluorinated C1-C8 alkyl, or SF5; and, R a , R b , R c ~R d Independently, Selected from H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c ~R d At least one, at least two, or at least three of the following: Selected from CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5.

[0310] According to a more preferred embodiment, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from heteroaryls and SF5, Here, R 1, R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from D, CN, CF3, partially fluorinated C1-C8 alkyl, fully fluorinated C1-C8 alkyl, or SF5; Here, R 1 , R 2 , R 3 , R 4 , and, R 5 At least one, at least two, or at least three of these are independent of each other. CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from heteroaryl and SF5.

[0311] According to a more preferred embodiment, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from heteroaryls and SF5, Here, C3~C is substituted. 40 Heteroaryls are sp 2 Carbon-fluorine substituted, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from D, CN, CF3, partially fluorinated C1-C8 alkyl, fully fluorinated C1-C8 alkyl, or SF5; and, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 At least one, at least two, or at least three of these are independent of each other. CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from heteroaryl and SF5.

[0312] According to one embodiment, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (where m=1 to 8 and t=1 to 2m is selected; and / or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1(m is 1-8), CC m F (2m+1)-t H t (m is selected from 1 to 8, and t is selected from 1 to 2m).

[0313] According to one embodiment, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (where m is 1 to 8 and t is 0 to 2m) or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t It is selected from (where t = 0 to 2m).

[0314] According to one embodiment, X 1 , X 2 , X 3 , X 4 , and, X 5 At least two or at least three of them independently, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CCm F (2m+1)-t H t (where m is 1 to 8 and t is 0 to 2m) or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CCF3, CSF5, CCN, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t It is selected from (where t = 0 to 2m).

[0315] According to one embodiment, X 1 , X 2 , X 3 , X 4 , and, X 5 At least three of these are independent, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (where m is 1 to 8 and t is 0 to 2m) or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of them is selected from N; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CCF3, CSF5, CCN, CC m F 2m+1(m is 1-8), CC m F (2m+1)-t H t It is selected from (where t = 0 to 2m).

[0316] According to one embodiment, X 1 , X 2 , X 3 , X 4 , and, X 5 At least three of these are independent, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (where m=1 to 8 and t=0 to 2m is selected; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CCF3, CSF5, CCN, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t It is selected from (where t = 0 to 2m).

[0317] According to one embodiment, X 1 , X 2 , X 3 , X 4 , and, X 5 At least three of these are independent, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (where m=1 to 8 and t=0 to 2m is selected; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5At least two of them, independently, CCF3, CSF5, CCN, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t It is selected from (where t = 0 to 2m).

[0318] According to one embodiment, X 1 , X 2 , X 3 , X 4 , and, X 5 At least three of these are independent, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (where m=1 to 8 and t=0 to 2m is selected; or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least two of them, independently, CCF3, CCN, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t It is selected from (where t = 0 to 2m).

[0319] According to one embodiment, in equations (I), (IVa), (IVb), (Va)~(VR), X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t(m is selected from 1 to 8 and t is selected from 0 to 2m.)

[0320] According to one embodiment, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CCF3, CCN, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t It is selected from (where t = 0 to 2m).

[0321] According to one embodiment, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independently selected from CCF3 or CCN.

[0322] According to one embodiment, All X 1 , X 2 , X 3 , X 4 , and, X 5 CR n (n is selected from 1 to 5) Furthermore, X 1 , X 2 , X 3 , X 4 , and, X 5 At least two or at least three of them independently, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m is selected from 1 to 8 and t is selected from 0 to 2m), or X 1 , X 2 , X 3 , X4 , and, X 5 The first three are selected from N, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one or at least two of them independently, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m is selected from 1 to 8, and t is selected from 0 to 2m).

[0323] According to one embodiment, X n At least two of them are CR n and CR n+1 (n is selected from 1 to 4) Here, the CR n and CR n+1 In R n and R n+1 At least one of them is selected from CN, The CR n and CR n+1 In R n and R n+1 At least one of them is CCF3, or CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m is selected from 1 to 8 and t is selected from 0 to 2m); or, Here, the CR n and CR n+1 In R n and R n+1 It is selected from CN.

[0324] According to one embodiment, X n At least two of them are CR n and CR n+1 (n is selected from 1 to 4) Here, the CR nand CR n+1 In R n and R n+1 At least one of them is selected from CN, R n and R n+1 At least one of them is selected from CCF3; or, Here, the CR n and CR n+1 In R n and R n+1 It is selected from CN.

[0325] According to one embodiment, X 1 , X 2 , X 3 , X 4 , and, X 5 Substituted or unsubstituted C-C3 heteroaryls from CC 40 Heteroaryls are independent of each other. From substituted or unsubstituted C-C3 heteroaryls to CC 24 Heteroaryl, substituted or unsubstituted C-C3 heteroaryls to CC 18 Heteroaryl, substituted or unsubstituted C-C3 heteroaryls to CC 12 Heteroaryls, substituted or unsubstituted C-C3 heteroaryls to C-C9 heteroaryls, substituted or unsubstituted C-C3 heteroaryls to C-C6 heteroaryls, Selected from.

[0326] According to one embodiment, X 1 , X 2 , X 3 , X 4 , and, X 5 Substitution or non-substitution of C-C6 aryl to CC 40 Ariel, independently, Substituted or unsubstituted C-C6 aryl to CC 24 From aryl, substituted or unsubstituted C-C6 aryl to CC 18 From aryl, substituted or unsubstituted C-C6 aryl to CC 12 From aryl, substituted or unsubstituted C-C6 aryl to CC 10Aryl, substituted or unsubstituted C-C6 aryl, Selected from.

[0327] According to one embodiment, X 1 ~X 5 At least one of them is independently selected from CH, CD, or N, preferably X 1 ~X 5 At least one of these is independently selected from CH or CD.

[0328] According to one embodiment, X 1 ~X 5 At least one or at least two of are independently selected from CH, CD, or N. According to one embodiment, X 1 ~X 5 At least one or at least two of are independently selected from CH or CD. According to one embodiment, the compound is sp 2 It does not contain F or Cl that are directly bonded to the hybrid carbon atoms.

[0329] This may further reduce the voltage rise over time in organic electronic devices, particularly those including a p-type charge generation layer.

[0330] According to one embodiment, in equations (I), (IVa), (IVb), (Va)~(VR), X 2 or X 4 These are R 2 or R 4 And R 2 or R 4 These are independently selected from CN, CF3, partially fluorinated C1-C8 alkyl, or fully fluorinated C1-C8 alkyl.

[0331] According to one embodiment in formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), X 1 , X 2 , X 3 , X 4 , and, X 5Of these, ≥0 and ≤3 are selected from N.

[0332] According to one embodiment in formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), X 1 , X 2 , X 3 , X 4 , and, X 5 Of these, ≥0 and ≤3, preferably ≥1 and ≤2, are selected from N.

[0333] According to one embodiment in formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), X 1 , X 2 , X 3 , X 4 , and, X 5 Of these, at least one, or at most two, are selected from N.

[0334] According to one embodiment, X 1 , X 2 , X 3 , X 4 , and, X 5 Of these, the total is 0, one, or two is N.

[0335] According to one embodiment in formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), at least two X 1 ~X 5 This is selected from CH, CD, or N.

[0336] According to one embodiment in formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), X 1 ~X 5 At least 3 to 5 of these are selected from CH, CD, or N.

[0337] According to one embodiment in formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), X 1 ~X5 At least four of these are selected from CH, CD, or N.

[0338] According to one embodiment in formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR), X 1 ~X 5 At least five of these are selected from CH, CD, or N.

[0339] [B 1 Equation (II) According to one embodiment, B in formula (II) 1 T1~T64:

[0340] [ka]

[0341] JPEG2026530313000071.jpg186169

[0342] Selected from.

[0343] According to one embodiment, B 1 The value is selected from T1 to T59.

[0344] According to one embodiment, B 1 The is selected from T1 to T14 and T60. According to one embodiment, B 1 The is selected from T18-T27 and T61-T64. According to one embodiment, B 1 The is selected from T48 to T59. According to one embodiment, B 1 The is selected from T52 to T59. According to a preferred embodiment, B 1 The is selected from T1 to T51 and T52 to T64. According to a more preferred embodiment, B 1 The is selected from T1 to T31 and T52 to T64. According to a more preferred embodiment, B 1 The elements are selected from T1 to T18, T52 to T56, and T60 to T64. According to the most preferred embodiment, B1 The is selected from T52 to T56. In a more preferred embodiment, B 1 The selection is made from T57 to T59.

[0345] [Equation (I)] According to one embodiment, the compound of formula (I) is D1 to D365 in Table I:

[0346] [Table 1]

[0347] JPEG2026530313000073.jpg255168

[0348] JPEG2026530313000074.jpg255169

[0349] JPEG2026530313000075.jpg255169

[0350] JPEG2026530313000076.jpg255168

[0351] JPEG2026530313000077.jpg255168

[0352] JPEG2026530313000078.jpg255169

[0353] JPEG2026530313000079.jpg255169

[0354] JPEG2026530313000080.jpg255167

[0355] JPEG2026530313000081.jpg255169

[0356] JPEG2026530313000082.jpg254169

[0357] JPEG2026530313000083.jpg245169

[0358] JPEG2026530313000084.jpg255166

[0359] JPEG2026530313000085.jpg255161

[0360] JPEG2026530313000086.jpg255166

[0361] JPEG2026530313000087.jpg252169

[0362] JPEG2026530313000088.jpg255164

[0363] JPEG2026530313000089.jpg255169

[0364] JPEG2026530313000090.jpg255168

[0365] JPEG2026530313000091.jpg254169

[0366] JPEG2026530313000092.jpg255165

[0367] JPEG2026530313000093.jpg254169

[0368] JPEG2026530313000094.jpg255169

[0369] JPEG2026530313000095.jpg254169

[0370] JPEG2026530313000096.jpg254169

[0371] JPEG2026530313000097.jpg254169

[0372] JPEG2026530313000098.jpg254169

[0373] JPEG2026530313000099.jpg255168

[0374] JPEG2026530313000100.jpg255169

[0375] JPEG2026530313000101.jpg255169

[0376] JPEG2026530313000102.jpg255169

[0377] JPEG2026530313000103.jpg255169

[0378] JPEG2026530313000104.jpg253169

[0379] JPEG2026530313000105.jpg255161

[0380] JPEG2026530313000106.jpg126169

[0381] Selected from.

[0382] According to one embodiment, the compound of formula (I) is selected from D1 to D365.

[0383] This may result in an even higher operating voltage.

[0384] According to one embodiment, the compound of formula (I) is selected from D1 to D156, D364, and D365.

[0385] This may further improve the operating voltage and the voltage rise over time. Furthermore, the stability of the compound, particularly against moisture, may be further improved. In addition, the volatility of the compound may be particularly suitable for the manufacture of organic electronic devices under thermal deposition conditions.

[0386] According to one embodiment, the compound of formula (I) is selected from D1 to D136, D364, and D365.

[0387] This may further improve the operating voltage and the voltage rise over time. Furthermore, the stability of the compound, particularly against moisture, may be further improved. In addition, the volatility of the compound may be particularly suitable for the manufacture of organic electronic devices under thermal deposition conditions.

[0388] According to one embodiment, the compound of formula (I) is selected from D1 to D121, D364, and D365.

[0389] This may further improve the operating voltage and the voltage rise over time. Furthermore, the stability of the compound, especially against moisture, may be further improved.

[0390] In addition, the volatility of the compound may make it particularly suitable for the manufacture of organic electronic devices under thermal deposition conditions.

[0391] According to one embodiment, the compound of formula (I) is compounds K1 to K365:

[0392] [ka]

[0393] JPEG2026530313000108.jpg198169

[0394] JPEG2026530313000109.jpg227169

[0395] JPEG2026530313000110.jpg228169

[0396] JPEG2026530313000111.jpg198169

[0397] JPEG2026530313000112.jpg216169

[0398] JPEG2026530313000113.jpg224169

[0399] JPEG2026530313000114.jpg231169

[0400] JPEG2026530313000115.jpg216169

[0401] JPEG2026530313000116.jpg217169

[0402] JPEG2026530313000117.jpg216169

[0403] JPEG2026530313000118.jpg216169

[0404] JPEG2026530313000119.jpg216169

[0405] JPEG2026530313000120.jpg216169

[0406] JPEG2026530313000121.jpg216169

[0407] JPEG2026530313000122.jpg221169

[0408] JPEG2026530313000123.jpg222169

[0409] JPEG2026530313000124.jpg193169

[0410] Selected from.

[0411] According to one embodiment, the compound of formula (I) is selected from K1 to K365. According to one embodiment, the compound of formula (I) is selected from K1 to K156, K364, and K365. According to one embodiment, the compound of formula (I) is selected from K1 to K136, K364, and K365. According to one embodiment, the compound of formula (I) is selected from K1 to K121, K364, and K365.

[0412] The operating voltage and the voltage rise over time may be further improved. In addition, the stability of the compound, particularly against moisture, may be further improved. Furthermore, the volatility of the compound may be particularly suitable for the manufacture of organic electronic devices under thermal deposition conditions.

[0413] [LUMO of the compound of formula (I)] According to one embodiment, the calculated LUMO of compounds of formulas (I), (IVa), (IVb), (VA)~(VH), and (VJ)~(VR) is such that the LUMO energy level is ≤-4.90eV, preferably ≤-4.95eV, when calculated using the program packages ORCA V5.0.3 (Max Planck Institute fur Kohlenforschung, Kaiser Wilhelm Platz 1, 45470, Muelheim / Ruhr, Germany) and WEASEL 1.9.2 (FAccTs GmbH, Rolandstrasse 67, 50677 Koln, Germany). The HOMO and LUMO energy levels of the molecular structure are determined by applying the hybrid functional B3LYP together with the def2-tzvp basis set to the optimized geometric structure obtained by applying the composite method HF-3c in the gas phase.

[0414] According to one embodiment, the calculated LUMO of compounds of formulas (I), (IVa), (IVb), (VA)~(VH), and (VJ)~(VR), when calculated using the program packages ORCA V5.0.3 (Max Planck Institute fur Kohlenforschung, Kaiser Wilhelm Platz 1, 45470, Muelheim / Ruhr, Germany) and WEASEL 1.9.2 (FAccTs GmbH, Rolandstrasse 67, 50677 Koln, Germany), is such that the LUMO energy levels are ≥-6.00eV to ≤-4.90eV, preferably ≥-6.00eV to ≤-4.95eV, and more preferably ≥-5.80eV to ≤-4.95eV. The HOMO and LUMO energy levels of the molecular structure are determined by applying the hybrid functional B3LYP, along with the def2-tzvp basis set, to the optimized geometric structure obtained by applying the composite method HF-3c in the gas phase.

[0415] This may further improve the operating voltage of organic electronic devices, particularly those including a p-type charge generation layer.

[0416] [Further Embodiments] According to one embodiment, the compound of formula (I) is represented as follows:

[0417] [ka]

[0418] [In formula (I), A 1 This is expressed by equation (II),

[0419] [ka]

[0420] In formula (II), B 1 It is expressed by equation (III),

[0421] [ka]

[0422] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; and / or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, X 1 ~X 5 At least one of them is independently selected from CH, CD, or N, preferably X 1 ~X 5 At least one of them is independently selected from CH or CD; R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; and, The following compounds E1-E5:

[0423] [ka]

[0424] [This is excluded.]

[0425] According to one embodiment, the compound of formula (I) is represented as follows:

[0426] [ka]

[0427] [In formula (I), A 1 This is expressed by equation (II),

[0428] [ka]

[0429] In formula (II), B 1 It is expressed by equation (III),

[0430] [ka]

[0431] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; and / or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1-8, and t=1-2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, X 1 ~X 5At least one of them is independently selected from CH, CD, or N, preferably X 1 ~X 5 At least one of them is independently selected from CH or CD; R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5; and, The following compounds E1-E5:

[0432] [ka]

[0433] [This is excluded.]

[0434] According to one embodiment, the compound of formula (I) is represented as follows:

[0435] [ka]

[0436] [In formula (I), A 1 This is expressed by equation (II),

[0437] [ka]

[0438] In formula (II), B 1 It is expressed by equation (III),

[0439] [ka]

[0440] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from the group including H, D, F, Cl, CN, CF3, and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F2m+1 (m is 1-8), or CC m F (2m+1)-t H t (where m=1 to 8 and t=1 to 2m is selected; and / or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (where m is between 1 and 8, and t is between 1 and 2m) Here, X 1 ~X 5 At least one of them is independently selected from CH, CD, or N, preferably X 1 ~X 5 At least one of them is independently selected from CH or CD; R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5; and, The following compounds E1-E5:

[0441] [ka]

[0442] [This is excluded.]

[0443] According to one embodiment, the compound of formula (I) is represented as follows:

[0444] [ka]

[0445] [In formula (I), A 1 This is expressed by equation (II),

[0446] [ka]

[0447] In formula (II), B 1 It is expressed by equation (III),

[0448] [ka]

[0449] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; and / or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; and, The following compounds E1-E5:

[0450] [ka]

[0451] [This is excluded.]

[0452] According to one embodiment, the compound of formula (I) is represented as follows:

[0453] [ka]

[0454] [In formula (I), A 1 This is expressed by equation (II),

[0455] [ka]

[0456] In formula (II), B 1 It is expressed by equation (III),

[0457] [ka]

[0458] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; and / or, X 1 , X 2 , X 3, X 4 , and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1-8, and t=1-2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5; and, The following compounds E1-E5:

[0459] [ka]

[0460] [This is excluded.]

[0461] According to one embodiment, the compound of formula (I) is represented as follows:

[0462] [ka]

[0463] [In formula (I), A 1 This is expressed by equation (II),

[0464] [ka]

[0465] In formula (II), B 1 It is expressed by equation (III),

[0466] [ka]

[0467] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from the group comprising H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5, Here, R1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (where m=1 to 8 and t=1 to 2m is selected; and / or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (where m is between 1 and 8, and t is between 1 and 2m) R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5; and, The following compounds E1-E5:

[0468] [ka]

[0469] [This is excluded.]

[0470] According to one embodiment, the compound of formula (I) is represented as follows:

[0471] [ka]

[0472] [In formula (I), A 1 This is expressed by equation (II),

[0473] [ka]

[0474] In formula (II), B 1 It is expressed by equation (III),

[0475] [ka]

[0476] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t(m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; and / or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1 to 8, and t = 1 to 2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, R a , R b , R c ~R d Independently, Selected from H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5, and not selected from halogens. Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5, The following compounds E1-E5:

[0477] [ka]

[0478] [This is excluded.]

[0479] According to one embodiment, the compound of formula (I) is represented as follows:

[0480] [ka]

[0481] [In formula (I), A 1 This is expressed by equation (II),

[0482] [ka]

[0483] In formula (II), B 1 It is expressed by equation (III),

[0484] [ka]

[0485] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; and / or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is 1-8, and t=1-2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; Here, R a , R b , R c ~R d Independently, Selected from H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5, and not selected from halogens. Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group including CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5, The following compounds E1-E5:

[0486] [ka]

[0487] [This is excluded.]

[0488] According to one embodiment, the compound of formula (I) is represented as follows:

[0489] [ka]

[0490] [In formula (I), A 1 This is expressed by equation (II),

[0491] [ka]

[0492] In formula (II), B 1 It is expressed by equation (III),

[0493] [ka]

[0494] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m = 1 to 8, and t = 1 to 2m) Selected from; and / or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is between 1 and 8, and t is between 1 and 2m) Selected from; Here, R a , R b , R c ~R d Independently, Selected from H, D, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5, and not selected from halogens. Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group including CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5, The following compounds E1-E5:

[0495] [ka]

[0496] [This is excluded.]

[0497] According to one embodiment, the compound of formula (I) is represented as follows:

[0498] [ka]

[0499] [In formula (I), A 1 This is expressed by equation (II),

[0500] [ka]

[0501] In formula (II), B 1 It is expressed by equation (III),

[0502] [ka]

[0503] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8, t=1~2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; and / or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t(m is 1 to 8, and t = 1 to 2m), COCF3, COC m F 2m+1 (m is 1-8), or COC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy or fully fluorinated C1-C8 alkoxy, and SF5; and, Here, the compound of formula (I) is sp 2 It does not contain F or Cl directly bonded to the hybrid carbon atoms; and, The following compounds E1-E5:

[0504] [ka]

[0505] [This is excluded.]

[0506] According to one embodiment, the compound of formula (I) is represented as follows:

[0507] [ka]

[0508] [In formula (I), A 1 This is expressed by equation (II),

[0509] [ka]

[0510] In formula (II), B 1 It is expressed by equation (III),

[0511] [ka]

[0512] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, substituted or unsubstituted C6-C 40Aryl, substituted or unsubstituted C3-C 40 Selected from the group including heteroaryls and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m=1~8 and t=1~2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; and / or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t(m is 1-8, and t=1-2m), from substituted or unsubstituted C-C6 aryl to CC 40 From aryl, substituted or unsubstituted C-C3 heteroaryls to CC 40 Heteroaryl, Selected from; R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5; and, Here, the compound of formula (I) is sp 2 It does not contain F or Cl directly bonded to the hybrid carbon atoms; and, The following compounds E1-E5:

[0513] [ka]

[0514] [This is excluded.]

[0515] According to one embodiment, the compound of formula (I) is represented as follows:

[0516] [ka]

[0517] [In formula (I), A 1 This is expressed by equation (II),

[0518] [ka]

[0519] In formula (II), B 1 It is expressed by equation (III),

[0520] [ka]

[0521] Here, the asterisk "*" indicates the bond position. X 1 CR 1 or selected from N; X 2 CR 2 or selected from N; X 3 CR 3 or selected from N; X 4 CR 4 or selected from N; X 5 CR 5 or selected from N; R 1 , R 2 , R 3 , R 4 , and, R 5 Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5, Here, R 1 , R 2 , R 3 , R 4 , and, R 5 The one or more substituents above are independent, Selected from the group comprising D, F, Cl, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, X 1 , X2 , X 3 , X 4 , and, X 5 At least one, at least two, or at least three of these are independent of each other. CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), or CC m F (2m+1)-t H t (m = 1 to 8, and t = 1 to 2m) Selected from; and / or, X 1 , X 2 , X 3 , X 4 , and, X 5 At least one of is selected from N; and / or, X 1 ~X 5 At least one of them is N, and X 1 ~X 5 At least one or at least two of them independently, CF, CCl, CSF5, CCN, CCF3, CC m F 2m+1 (m is 1-8), CC m F (2m+1)-t H t (m is between 1 and 8, and t is between 1 and 2m) Selected from; R a , R b , R c ~R d Independently, Selected from the group comprising H, D, F, Cl, CN, CF3, partially fluorinated or fully fluorinated C1-C8 alkyl groups, and SF5; Here, R a , R b , R c , and, R d At least one, at least two, or at least three of these are independent of each other. Selected from the group comprising F, Cl, CN, CF3, partially fluorinated C1-C8 alkyl or fully fluorinated C1-C8 alkyl, and SF5; and, Here, the compound of formula (I) is sp 2 It does not contain F or Cl directly bonded to the hybrid carbon atoms; and, The following compounds E1-E5:

[0522] [ka]

[0523] [This is excluded.]

[0524] [Organic semiconductor layer] The present invention further relates to an organic semiconductor layer comprising a compound or composition according to the present invention.

[0525] The present invention further relates to an organic semiconductor layer comprising compounds according to formulas (I), (IVa), (IVb), (VA)~(VH), and (VJ)~(VR).

[0526] According to one embodiment, the organic semiconductor layer comprises a compound of formula (I), where the compound of formula (I) is preferably a compound of formulas (VA) to (VH) and (VJ) to (VR).

[0527] According to one embodiment, the organic semiconductor layer comprises a compound of formula (I), where the compound of formula (I) is preferably a compound of formulas (VA) to (VH) and (VJ) to (VR), and the organic semiconductor layer comprises a hole transport matrix compound.

[0528] According to one embodiment, the organic semiconductor layer is a hole injection layer or a p-type charge generation layer.

[0529] The present invention further relates to an organic semiconductor layer, the organic semiconductor layer comprising compounds according to formulas (VA) to (VH) and (VJ) to (VR), preferably selected from compounds K1 to K352, or selected from compounds K1 to K156, K1 to K136, or K1 to K121.

[0530] When an organic semiconductor layer contains a compound according to the present invention, the term “compound of formula (I)” throughout this specification is intended to also include a composition containing at least one of the compounds according to the present invention as described above.

[0531] When an organic semiconductor layer contains a compound according to the present invention, the term “compound of formula (I)” throughout this specification is intended to also include a composition containing at least one of the compounds according to the present invention as described above.

[0532] According to one embodiment, the organic semiconductor layer and / or compounds of formulas (I), (IVa), (IVb), (VA)~(VH) and (VJ)~(VR) are non-luminescent.

[0533] In the context of this specification, the terms “essentially non-luminescent” or “non-luminescent” mean that the contribution of the compound or layer from the device to the visible emission spectrum is less than 10%, preferably less than 5%, of the visible emission spectrum. The visible emission spectrum is the emission spectrum with wavelengths from about ≥380 nm to about ≤780 nm.

[0534] According to one embodiment of the present invention, at least one organic semiconductor layer may further include at least one matrix compound, also known as a covalent matrix compound or substantially covalent matrix compound.

[0535] [Substantially covalent matrix compounds] The organic semiconductor layer may further comprise a covalent matrix compound, also called a substantially covalent matrix compound. According to one embodiment, the substantially covalent matrix compound may be selected from at least one organic compound. The substantially covalent matrix may consist of substantially covalently bonded C, H, O, N, S, and the matrix may further optionally comprise covalently bonded B, P, As, and / or Se.

[0536] According to one embodiment of an organic electronic device, the organic semiconductor layer further comprises a substantially covalent matrix compound, which may be selected from an organic compound consisting of substantially covalently bonded C, H, O, N, S, and which may further optionally contain covalently bonded B, P, As, and / or Se.

[0537] Organometallic compounds containing carbon-metal covalent bonds, metal complexes containing organic ligands, and metal salts of organic acids are further examples of organic compounds that can function as substantially covalent matrix compounds in hole implantation layers.

[0538] In one embodiment, the substantially covalent matrix compound may lack metal atoms, and the majority of its skeletal atoms may be selected from C, O, S, and N. Alternatively, the substantially covalent matrix compound may lack metal atoms, and the majority of its skeletal atoms may be selected from C and N.

[0539] According to one embodiment, the substantially covalent matrix compound may have a molecular weight Mw of ≥400 g / mol and ≤2000 g / mol, preferably ≥450 g / mol and ≤1500 g / mol, more preferably ≥500 g / mol and ≤1000 g / mol, and additionally preferably ≥550 g / mol and ≤900 g / mol, and similarly preferably ≥600 g / mol and ≤800 g / mol.

[0540] Preferably, the substantially covalent matrix compound comprises at least one arylamine moiety, or diarylamine moiety, or triarylamine moiety.

[0541] Preferably, the substantially covalent matrix compound does not contain metal and / or ionic bonds.

[0542] [Compounds of formula (VI) or compounds of formula (VII)] In another embodiment, at least one matrix compound (also called a “substantially covalent matrix compound”) is at least one arylamine compound, diarylamine compound, triarylamine compound, compound of formula (VI), or compound of formula (VII):

[0543] [ka]

[0544] It may include, Here: T 1 , T 2 , T 3 , T 4 , and, T 5 This is independently selected from a single bond, phenylene, biphenylene, terphenylene, or naphthenylene, preferably selected from a single bond or phenylene; T 6 These are phenylene, biphenylene, terphenylene, or naphthenylene; Ar 1 Ar 2 Ar 3 Ar 4 , and, Ar 5 Independently, Substitution or non-substitution of C6~C 20 Aryl, or substituted or unsubstituted C3-C 20Heteroarylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted triphenylene, substituted or unsubstituted tetracene, substituted or unsubstituted tetrafen, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthene, substituted or unsubstituted carbazole, substituted 9-phenylcarbazole, substituted or unsubstituted azepine, substituted or unsubstituted dibenzo[b,f]azepine, substituted or Unsubstituted 9,9'-spirobi[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanthene], or substituted or unsubstituted aromatic ring fusion systems comprising at least three substituted or unsubstituted aromatic rings selected from the group comprising substituted or unsubstituted nonhetero, substituted or unsubstituted hetero 5-membered rings, substituted or unsubstituted 6-membered rings and / or substituted or unsubstituted 7-membered rings, and substituted or unsubstituted fluorene; or ring fusion systems comprising 2 to 6 substituted or unsubstituted 5 to 7-membered rings, wherein the rings are selected from the group comprising: (i) unsaturated 5 to 7-membered rings of heterocycles, (ii) 5 to 6-membered rings of aromatic heterocycles, (iii) unsaturated 5 to 7-membered rings of nonheterocycles, (iv) 6-membered rings of aromatic nonheterocycles; Here, Ar 1 Ar 2 Ar 3 Ar 4 , and, Ar 5 The substituents are H, D, F, C(-O)R 2 , CN, Si(R 2 )3, P(-O)(R 2 )2, OR 2 , S(-O)R 2 S(-O)2R 2, substituted or unsubstituted linear alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted branched alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl or alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic ring systems having 6 to 40 aromatic ring atoms, and substituted or unsubstituted heteroaromatic ring systems having 5 to 40 aromatic ring atoms, unsubstituted C6-C 18 Aryl and unsubstituted C3-C 18 Selected from the same or different group as heteroaryls and fused ring systems containing 2 to 6 unsubstituted 5 to 7 membered rings, the rings are Selected from the group including heterocyclic unsaturated 5- to 7-membered rings, aromatic heterocyclic 5- to 6-membered rings, non-heterocyclic unsaturated 5- to 7-membered rings, and aromatic non-heterocyclic 6-membered rings. R 2 This includes H, D, a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 1 to 6 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms, an alkenyl or alkynyl group having 2 to 6 carbon atoms, and C6-C 18 Aryl or C3~C 18 A heteroaryl group may be selected.

[0545] According to one embodiment, T 1 , T 2 , T 3 , T 4 , and, T 5 T may be independently selected from a single bond, phenylene, biphenylene, or terphenylene. According to one embodiment, 1 , T 2 , T 3 , T 4 , and, T 5 T may be independently selected from phenylene, biphenylene, or terphenylene, and 1 , T 2 , T 3 , T 4 , and, T 5 One of these is a single bond. According to one embodiment, T1 , T 2 , T 3 , T 4 , and, T 5 T may be independently selected from phenylene or biphenylene, and 1 , T 2 , T 3 , T 4 , and, T 5 One of these is a single bond. According to one embodiment, T 1 , T 2 , T 3 , T 4 , and, T 5 T may be independently selected from phenylene or biphenylene, and 1 , T 2 , T 3 , T 4 , and, T 5 Two of them are single bonds.

[0546] According to one embodiment, T 1 , T 2 , and, T 3 It may be independently selected from phenylene, and T 1 , T 2 , and T 3 One of these is a single bond. According to one embodiment, T 1 , T 2 , and, T 3 This may be independently selected from phenylene, and T 1 , T 2 , and T 3 Two of them are single bonds.

[0547] According to one embodiment, T 6 This may be phenylene, biphenylene, or terphenylene. According to one embodiment, T 6 T may be phenylene. According to one embodiment, 6 T may be biphenylene. According to one embodiment, 6 It may be terphenylene.

[0548] According to one embodiment, Ar 1 Ar 2 Ar 3 Ar 4 , and, Ar 5 These are independently, W1~W16:

[0549] [ka]

[0550] You may choose from the following: Here, the asterisk "*" indicates the join position.

[0551] According to one embodiment, Ar 1 Ar 2 Ar 3 Ar 4 , and, Ar 5 These may be independently selected from W1 to W15, or selected from W1 to W10 and W13 to W15.

[0552] According to one embodiment, Ar 1 Ar 2 Ar 3 Ar 4 , and, Ar 5 These may be independently selected from the group consisting of W1, W2, W5, W7, W9, W10, and W13-W16.

[0553] Ar 1 Ar 2 Ar 3 Ar 4 , and, Ar 5 If selected within this range, the rate onset temperature may be within a range particularly suitable for mass production.

[0554] The "matrix compound of formula (VI) or formula (VII)" may also be called a "hole transport compound."

[0555] According to one embodiment, the substantially covalent matrix compound comprises at least one naphthyl group, carbazole group, dibenzofuran group, dibenzothiophene group, and / or substituted fluorenyl group, where the substituent is independently selected from methyl, phenyl, or fluorenyl.

[0556] According to the embodiment of the electronic device, the matrix compound of formula (VI) or formula (VII) is L1 to L23:

[0557] [ka]

[0558] JPEG2026530313000176.jpg184169

[0559] JPEG2026530313000177.jpg250169

[0560] Selected from.

[0561] [Organic Electronic Devices] The present invention further relates to an organic electronic device comprising an anode layer, a cathode layer, and at least one organic semiconductor layer, wherein the at least one organic semiconductor layer is disposed between the anode layer and the cathode layer, and the at least one organic semiconductor layer is an organic semiconductor layer according to the present invention.

[0562] According to one embodiment of the organic electronic device according to the present invention, the anode layer includes at least a first anode sublayer and a second anode sublayer.

[0563] According to one embodiment, the organic electronic device further includes at least one photoactive layer, the at least one photoactive layer being located between the anode layer and the cathode layer, and at least one of the at least one organic semiconductor layer being located between the anode layer and the at least one photoactive layer.

[0564] According to one embodiment, the organic semiconductor layer is a hole injection layer.

[0565] According to one embodiment, the hole injection layer is in direct contact with the anode layer.

[0566] According to one embodiment, the hole injection layer is in direct contact with the anode layer, and the anode layer is in direct contact with the substrate, where the substrate is selected from a glass substrate, a plastic substrate, a metal substrate, or a backplane.

[0567] According to one embodiment, the photoactive layer is a light-emitting layer.

[0568] According to one embodiment, the organic electronic device is an electroluminescent device, an organic light-emitting diode (OLED), a light-emitting device, a thin-film transistor, a battery, a display device, or an organic solar cell (OPV).

[0569] According to one embodiment, the organic semiconductor layer is a p-type charge generation layer.

[0570] According to one embodiment, the organic electronic device includes at least two light-emitting layers, wherein at least one of the at least one organic semiconductor layers is located between a first light-emitting layer and a second light-emitting layer.

[0571] According to one embodiment, the organic electronic device is an electroluminescent device, preferably an organic light-emitting diode.

[0572] According to one embodiment, the organic electronic device further includes a substrate.

[0573] According to one embodiment of the present invention, the organic electronic device is an organic light-emitting diode comprising a substrate, an anode layer, an organic semiconductor layer containing a compound of formula (I), a light-emitting layer, an optional electron transport layer, an optional electron injection layer, and a cathode layer. The organic light-emitting diode may further include a p-type charge generation layer, the p-type charge generation layer being located between the anode layer and the cathode layer, and the p-type layer containing a compound of formula (I).

[0574] According to one embodiment of the present invention, an organic electronic device comprises an anode layer, a cathode layer, and at least one organic semiconductor layer, wherein the at least one organic semiconductor layer is located between the anode layer and the cathode layer, and the at least one organic semiconductor layer is a hole injection layer and / or a p-type charge generation layer according to the present invention.

[0575] The organic electronic device includes a first electrode, a second electrode, a first photoactive layer, a second photoactive layer, and a charge generation layer. The charge generation layer is positioned between the first photoactive layer and the second photoactive layer; The charge generation layer includes an n-type charge generation layer and a p-type charge generation layer; The p-type charge generation layer contains the compound of formula (I).

[0576] The organic electronic device includes an anode layer, a cathode layer, a first photoactive layer, a second photoactive layer, and a charge generation layer. The charge generation layer is positioned between the first photoactive layer and the second photoactive layer; The charge generation layer includes an n-type charge generation layer and a p-type charge generation layer; The p-type charge generation layer contains the compound of formula (I).

[0577] The organic electronic device includes an anode layer, a cathode layer, a first light-emitting layer, a second light-emitting layer, and a charge generation layer. The charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The charge generation layer includes an n-type charge generation layer and a p-type charge generation layer; The n-type charge generation layer is located closer to the anode layer than the p-type charge generation layer; The p-type charge generation layer contains the compound of formula (I).

[0578] The organic electronic device includes a first electrode, a second electrode, a first photoactive layer, a second photoactive layer, and a charge generation layer. The charge generation layer is positioned between the first photoactive layer and the second photoactive layer; The charge generation layer includes an n-type charge generation layer and a p-type charge generation layer; The p-type charge generation layer contains the compound of formula (I), The n-type charge generation layer comprises a metal dopant, which is preferably selected from alkali metals, alkaline earth metals, or rare earth metals, and more preferably selected from Li, Mg, or Yb.

[0579] The organic electronic device includes an anode layer, a cathode layer, a first photoactive layer, a second photoactive layer, and a charge generation layer. The charge generation layer is positioned between the first photoactive layer and the second photoactive layer; The charge generation layer includes an n-type charge generation layer and a p-type charge generation layer; The p-type charge generation layer contains the compound of formula (I), The n-type charge generation layer comprises a metal dopant, which is preferably selected from alkali metals, alkaline earth metals, or rare earth metals, and more preferably selected from Li, Mg, or Yb.

[0580] The organic electronic device includes an anode layer, a cathode layer, a first light-emitting layer, a second light-emitting layer, and a charge generation layer. The charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The charge generation layer includes an n-type charge generation layer and a p-type charge generation layer; The n-type charge generation layer is located closer to the anode layer than the p-type charge generation layer; The p-type charge generation layer contains the compound of formula (I), The n-type charge generation layer comprises a metal dopant, which is preferably selected from alkali metals, alkaline earth metals, or rare earth metals, and more preferably selected from Li, Mg, or Yb.

[0581] According to one embodiment of the present invention, an electronic organic device is an organic light-emitting diode comprising a substrate, an anode layer, a hole injection layer optionally containing a compound of formula (I), a first light-emitting layer, a charge generation layer including a p-type charge generation layer containing a compound of formula (I), a second light-emitting layer, an optional electron transport layer, an optional electron injection layer, and a cathode layer.

[0582] According to one embodiment of the present invention, an electronic organic device is an organic light-emitting diode comprising a substrate, an anode layer, a hole injection layer optionally containing a compound of formula (I), a first light-emitting layer, a charge generation layer including a p-type charge generation layer containing a compound of formula (I), and an n-type charge generation layer containing a metal dopant (wherein preferably the metal dopant is selected from alkali metals, alkaline earth metals, or rare earth metals, more preferably from Li, Mg, or Yb), a second light-emitting layer, an optional electron transport layer, an optional electron injection layer, and a cathode layer.

[0583] The present invention further relates to a display device including an organic electronic device according to the present invention.

[0584] [Further layers] According to the present invention, the organic electronic device may include further layers in addition to the layers already described above. Exemplary embodiments of each layer are described below: (substrate) The substrate may be any substrate commonly used in the manufacture of electronic devices such as organic light-emitting diodes. If light is emitted through the substrate, the substrate should be made of a transparent or translucent material (e.g., a glass substrate or a transparent plastic substrate). If light is emitted through the top surface, the substrate may be made of both transparent and opaque materials, such as a glass substrate, a plastic substrate, a metal substrate, a silicon substrate, or a backplane.

[0585] (Anode layer) The anode layer may be formed by depositing or sputtering the material used to form the anode layer. The material used to form the anode layer may be a high work function material to facilitate hole injection. The anode material may be selected from low work function materials (i.e., aluminum). The anode electrode may be a transparent electrode or a reflective electrode. Transparent conductive oxides (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), aluminum zinc oxide (AlZO), and zinc oxide (ZnO)) may be used to form the anode electrode. The anode layer may also be formed using a metal, typically silver (Ag), gold (Au), or a metallic alloy.

[0586] According to one embodiment, the anode layer includes a first anode sublayer and a second anode sublayer, where, The first anode sublayer contains a first metal whose work function is in the range of ≥4eV and ≤6eV. The second anode sublayer contains a transparent conductive oxide; The second anode sublayer is positioned closer to the hole injection layer.

[0587] According to one embodiment, the first metal of the first anode sublayer may be selected from the group including Ag, Mg, Al, Cr, Pt, Au, Pd, Ni, Nd, and Ir, preferably Ag, Au, or Al, and more preferably Ag.

[0588] According to one embodiment, the first anode sublayer has a thickness in the range of 5 to 200 nm, or in the range of 8 to 180 nm, or in the range of 8 to 150 nm, or in the range of 100 to 150 nm.

[0589] According to one embodiment, the first anode sublayer is formed by depositing a first metal by vacuum thermal deposition.

[0590] It should be understood that the first anode layer is not part of the substrate.

[0591] According to one embodiment, the transparent conductive oxide of the second anode sublayer is selected from the group including indium tin oxide or indium zinc oxide, and more preferably indium tin oxide.

[0592] According to one embodiment, the second anode sublayer may have a thickness in the range of 3 to 200 nm, or in the range of 3 to 180 nm, or in the range of 3 to 150 nm, or in the range of 3 to 20 nm.

[0593] According to one embodiment, the second anode sublayer may be formed by sputtering a transparent conductive oxide.

[0594] According to one embodiment, the anode layer of an organic electronic device further includes a third anode sublayer comprising a transparent conductive oxide, the third anode sublayer being positioned between the substrate and the first anode sublayer.

[0595] According to one embodiment, the third anode sublayer comprises a transparent oxide, preferably selected from the group comprising indium tin oxide or indium zinc oxide, and more preferably indium tin oxide.

[0596] According to one embodiment, the third anode sublayer may have a thickness in the range of 3 to 200 nm, or in the range of 3 to 180 nm, or in the range of 3 to 150 nm, or in the range of 3 to 20 nm.

[0597] According to one embodiment, the third anode sublayer may be formed by sputtering a transparent conductive oxide.

[0598] It should be understood that the third anode layer is not part of the substrate.

[0599] According to one embodiment, the anode layer includes a first anode sublayer made of Ag, a second anode sublayer made of a transparent conductive oxide (preferably ITO), and a third anode sublayer made of a transparent conductive oxide (preferably ITO); the first anode sublayer is positioned between the second anode sublayer and the third anode sublayer.

[0600] (Hole transport layer) According to one embodiment, the organic electronic device includes a hole transport layer, which is located between a hole injection layer and at least one first light-emitting layer.

[0601] The hole transport layer (HTL) may be formed on the HIL by methods such as vacuum deposition, spin coating, slot die coating, printing, casting, or Langmuir-Bludget (LB) deposition. When the HTL is formed by vacuum deposition or spin coating, the deposition and coating conditions may be similar to those for HIL formation. However, the conditions for vacuum deposition or solution deposition may differ depending on the compound used for HTL formation.

[0602] HTLs may be formed from any compound commonly used for HTL formation. Suitable compounds are disclosed, for example, in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010, which is incorporated by reference. Examples of compounds that may be used to form HTLs are: carbazole derivatives (e.g., N-phenylcarbazole or polyvinylcarbazole); benzidine derivatives (e.g., N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N',N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine (α-NPD)); and triphenylamine compounds (e.g., 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA)). Of these compounds, TCTA can transport holes and suppress the diffusion of excitons into the EML.

[0603] According to one embodiment, the hole transport layer may include the substantially covalent matrix compound described above.

[0604] According to one embodiment, the hole transport layer may contain the compound of formula (VI) or (VII) described above.

[0605] According to one embodiment, the hole injection layer and the hole transport layer comprise the same substantially covalent matrix compound as described above.

[0606] According to one embodiment, the hole injection layer and the hole transport layer comprise the same compound of formula (VI) or (VII) described above.

[0607] The thickness of the HTL may be in the range of about 5 nm to about 250 nm, preferably in the range of about 10 nm to about 200 nm, more preferably in the range of about 20 nm to about 190 nm, more preferably in the range of about 40 nm to about 180 nm, more preferably in the range of about 60 nm to about 170 nm, more preferably in the range of about 80 nm to about 160 nm, more preferably in the range of about 100 nm to about 160 nm, and more preferably in the range of about 110 nm to about 140 nm.

[0608] If the thickness of the HTL is within this range, the HTL may have excellent hole transport characteristics without a substantial penalty to the drive voltage.

[0609] (Electron barrier layer) The function of the electron barrier layer (EBL) is to prevent electrons from moving from the light-emitting layer to the hole transport layer, thereby confining electrons to the light-emitting layer. This improves efficiency, operating voltage, and / or lifetime. Typically, the electron barrier layer contains a triarylamine compound. The triarylamine compound may have a LUMO level closer to the vacuum level than the LUMO level of the hole transport layer. The electron barrier layer may have a HOMO level further from the vacuum level compared to the HOMO level of the hole transport layer. The thickness of the electron barrier layer may be selected from 2 to 20 nm.

[0610] When the electron-blocking layer has a high triplet level, the electron-blocking layer may also be called a triplet-controlled layer.

[0611] The function of the triplet control layer is to reduce triplet quenching when using a phosphorescent green or blue light-emitting layer. This enables high luminescence efficiency from the phosphorescent light-emitting layer. The triplet control layer is selected from triarylamine compounds having a triplet level higher than the triplet level of the phosphorescent material in the adjacent light-emitting layer. Suitable compounds for the triplet control layer, particularly triarylamine compounds, are described in EP2 722 908 A1.

[0612] (Photoactive layer (PAL)) The photoactive layer converts electric current into photons or photons into electric current. The PAL may be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When the PAL is formed using vacuum deposition or spin coating, the deposition and coating conditions may be similar to those for forming the HIL. However, the deposition and coating conditions may differ depending on the compound used to form the PAL. The photoactive layer may be configured so as not to contain a metal complex according to formula (I). The photoactive layer may be an emissive layer or an absorbent layer.

[0613] According to one embodiment, the organic electronic device further includes at least one photoactive layer, the at least one photoactive layer being located between an anode layer and a cathode layer; preferably, at least one of the at least one organic semiconductor layer being located between the anode layer and the at least one photoactive layer.

[0614] According to one embodiment, the photoactive layer may be a light-emitting layer.

[0615] (Emitting Layer (EML)) EMLs may be formed on HTLs by methods such as vacuum deposition, spin coating, slot die coating, printing, casting, or LB deposition. When EMLs are formed using vacuum deposition or spin coating, the deposition and coating conditions may be similar to those for HIL formation. However, the deposition and coating conditions may differ depending on the compound used to form the EML.

[0616] According to one embodiment, the light-emitting layer does not contain the compound of formula (I).

[0617] The luminescent layer (EML) may be formed by a combination of host and luminescent dopant. Examples of hosts include Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4''-tris(carbazole-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distylyl arylene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazolate)zinc (Zn(BTZ)2).

[0618] The luminescent dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters that emit light via a thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their high efficiency. The emitter may be a low molecular weight or polymer.

[0619] Examples of red-emitting dopants include, but are not limited to, PtOEP, Ir(piq)3, and Btp2lr(acac). While these compounds are phosphorescent, fluorescent red-emitting dopants may also be used.

[0620] Examples of phosphorescent green dopants include Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2 (acac), and Ir(mpyp)3.

[0621] Examples of phosphorescent blue-emitting dopants include F2Irpic, (F2ppy)2Ir(tmd), and Ir(dfppz)3, and ter-fluorene. 4,4'-bis(4-diphenylamiostyryl)biphenyl (DPAVBi) and 2,5,8,11-tetra-tert-butylperylene (TBPe) are examples of fluorescent blue-emitting dopants.

[0622] The amount of luminescent dopant may range from about 0.01 to about 50 parts by weight, based on 100 parts by weight of host. Alternatively, the luminescent layer may consist of a luminescent polymer. The EML may have a thickness of about 10 nm to about 100 nm (e.g., about 20 nm to about 60 nm). When the thickness of the EML is within this range, the EML may have excellent luminescence without a substantial penalty to the driving voltage.

[0623] (Hole-Blocking Layer (HBL)) To prevent holes from diffusing into the ETL, a hole-blocking layer (HBL) may be formed on the EML by methods such as vacuum deposition, spin coating, slot die coating, printing, casting, or LB deposition. If the EML contains a phosphorescent dopant, the HBL may also have triplet exciton blocking properties.

[0624] HBL may also be referred to as auxiliary ETL or a-ETL.

[0625] When HBLs are formed using vacuum deposition or spin coating, the deposition and coating conditions may be similar to those for HIL formation. However, the deposition and coating conditions may differ depending on the compound used to form the HBL. Any compound commonly used to form HBLs may be used. Examples of compounds for forming HBLs include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and azine derivatives, preferably triazine or pyrimidine derivatives.

[0626] The HBL may have a thickness in the range of approximately 5 nm to approximately 100 nm (for example, approximately 10 nm to approximately 30 nm). When the thickness of the HBL is within this range, the HBL may have excellent hole blocking characteristics without a substantial penalty to the drive voltage.

[0627] (Electron transport layer (ETL)) The organic electronic device according to the present invention may further include an electron transport layer (ETL).

[0628] According to another embodiment, the electron transport layer may further contain an azine compound, preferably a triazine compound.

[0629] In one embodiment, the electron transport layer may further contain a dopant selected from alkali metal organic complexes, preferably LiQ.

[0630] The thickness of the ETL may be in the range of approximately 15 nm to approximately 50 nm (for example, approximately 20 nm to approximately 40 nm). When the thickness of the ETL is within this range, the ETL has a substantial drive voltage. It may have sufficient electron injection characteristics without incurring any penalties.

[0631] According to another embodiment, the organic electronic device may further include a hole-blocking layer and an electron-transporting layer, the hole-blocking layer and the electron-transporting layer comprising an azine compound. Preferably, the azine compound is a triazine compound.

[0632] (Electron injection layer (EIL)) Any EIL may be formed on the ETL (preferably directly on the electron transport layer), and such EIL may facilitate electron injection from the cathode. Examples of materials for forming the EIL include lithium 8-hydroxyquinolinolate (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, and Mg, all of which are known in the art. The deposition and coating conditions for forming the EIL are similar to those for forming the HIL, although the deposition and coating conditions may differ depending on the material used to form the EIL.

[0633] The thickness of the EIL may be in the range of approximately 0.1 nm to approximately 10 nm (for example, approximately 0.5 nm to approximately 9 nm). When the thickness of the EIL is within this range, the EIL may have sufficient electron injection characteristics without a substantial penalty to the drive voltage.

[0634] (Charge generation layer) The organic electronic device according to the present invention may further include a charge generation layer, which is a p-type charge generation layer (p-CGL), and the p-type charge generation layer is positioned close to the cathode layer.

[0635] The charge generation layer may further include an n-type charge generation layer (n-CGL), which is positioned between the p-type charge generation layer and the anode layer.

[0636] Preferably, the n-type charge generation layer and the p-type charge generation layer are arranged to be in direct contact.

[0637] The thickness of the n-CGL may be in the range of approximately 0.5 nm to approximately 15 nm (for example, approximately 1 nm to approximately 10 nm). When the thickness of the n-CGL is within this range, the EIL may have sufficient electron injection characteristics without a substantial penalty to the drive voltage.

[0638] n-CGL may contain a metal dopant, which is selected from alkali metals, alkaline earth metals, or rare earth metals, and is preferably selected from Li, Mg, or Yb.

[0639] n-CGL may contain an azine compound. In a preferred embodiment, nCGL may contain an azine compound and a metal dopant, the metal dopant being selected from alkali metals, alkaline earth metals, or rare earth metals.

[0640] (Cathode layer) The cathode layer is formed on an ETL or any EIL. The cathode layer may be formed from a metal, alloy, conductive compound, or a mixture thereof. The cathode electrode may have a low work function. For example, the cathode layer may be formed from lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), etc. Alternatively, the cathode electrode may be formed from a transparent conductive oxide such as ITO or IZO.

[0641] The thickness of the cathode layer may range from approximately 5 nm to approximately 1000 nm (for example, approximately 10 nm to approximately 100 nm). When the thickness of the cathode layer is in the range of approximately 5 nm to approximately 50 nm, the cathode layer may be transparent or translucent, even if it is formed from a metal or metal alloy.

[0642] It should be understood that the cathode layer is not part of the electron injection layer or electron transport layer.

[0643] (Organic Light-Emitting Diode (OLED)) The organic electronic device according to the present invention may also be an organic light-emitting device.

[0644] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a substrate; an anode layer formed on the substrate; a hole injection layer containing a compound of formula (I); a hole transport layer; a light-emitting layer; an electron transport layer; and a cathode layer.

[0645] In another embodiment, an OLED is provided, comprising a substrate; an anode layer formed on the substrate; a hole injection layer containing a compound of formula (I); a hole transport layer; an electron barrier layer; an emissive layer; a hole barrier layer; an electron transport layer; and a cathode layer.

[0646] In another embodiment, an OLED is provided comprising a substrate; an anode layer formed on the substrate; a hole injection layer containing a compound of formula (I); a hole transport layer; an electron barrier layer; an emissive layer; a hole barrier layer; an electron transport layer; an electron injection layer; and a cathode layer.

[0647] According to various embodiments, an OLED layer may be provided between the above layers, either on the substrate or on the top layer.

[0648] For example, the OLED shown in Figure 3 may be formed by sequentially forming an anode (120), a hole injection layer (130) which may contain a compound of formula (I), a hole transport layer (140), an electron barrier layer (145), an emissive layer (150), a hole barrier layer (155), an electron transport layer (160), an electron injection layer (180), and a cathode layer (190) on a substrate (110) in that order.

[0649] In one embodiment, the OLED may include the following layer structure: a substrate adjacent to an anode layer, the anode layer adjacent to a hole injection layer, the hole injection layer adjacent to a first hole transport layer, the first hole transport layer adjacent to a first electron barrier layer, the first electron barrier layer adjacent to a first light-emitting layer, the first light-emitting layer adjacent to a first electron transport layer, the first electron transport layer adjacent to an n-type charge generation layer, the n-type charge generation layer adjacent to a p-type charge generation layer, the p-type charge generation layer adjacent to a second hole transport layer, the second hole transport layer adjacent to a second electron barrier layer, the second electron barrier layer adjacent to a second light-emitting layer, and any electron transport layer and / or injection layer between the second light-emitting layer and the cathode layer.

[0650] The organic semiconductor layer according to the present invention may be a first hole injection layer and / or a p-type charge generation layer.

[0651] According to one embodiment, the organic semiconductor layer comprising the compound of formula (I) is a hole injection layer and / or a p-type charge generation layer.

[0652] (Organic electronic devices) The organic electronic device according to the present invention may be a light-emitting device or a solar cell, and preferably a light-emitting device.

[0653] In another embodiment, a method for manufacturing an organic electronic device is provided, the method using the following: At least one sedimentary source, preferably two, and more preferably at least three.

[0654] Suitable deposition methods include the following: Deposition by vacuum thermal deposition; Deposition by solution treatment, preferably selected from spin coating, printing, and casting; and / or, Slot die coating.

[0655] According to various embodiments, methods using the following are provided: A first deposit source that releases a compound of formula (I) according to the present invention, and A second deposit source that releases essentially covalent matrix compounds; The method includes the step of forming a hole injection layer, thereby enabling the organic light-emitting diode (OLED) to: The hole injection layer is formed by releasing a compound of formula (I) according to the present invention from a first deposit source and a substantially covalent matrix compound from a second deposit source.

[0656] According to various embodiments, the method may further include the steps of forming at least one layer on the anode layer, selected from the group consisting of forming a hole transport layer or forming a hole blocking layer, and forming an emissive layer between the anode layer and the first electron transport layer.

[0657] According to various embodiments, the method may further include the step of forming an organic light-emitting diode (OLED). Form an anode layer on the substrate. A hole injection layer containing the compound of formula (I) is formed on the anode layer. A hole transport layer is formed on a hole injection layer containing the compound of formula (I). A light-emitting layer is formed on the hole transport layer. An electron transport layer is formed on the light-emitting layer, and optionally a hole-blocking layer is formed on the light-emitting layer. And finally, the cathode layer is formed. Optionally, a hole-blocking layer is formed between the first anode layer and the light-emitting layer in this order. Optionally, an electron injection layer is formed between the electron transport layer and the cathode layer.

[0658] According to various embodiments, the OLED may have the following layer structure, and the order of the layers is as follows: an anode layer, a hole injection layer containing a compound of formula (I) according to the present invention, a first hole transport layer, a second hole transport layer, an emitting layer, an optional hole blocking layer, an electron transport layer, an optional electron injection layer, and a cathode layer.

[0659] According to another aspect of the present invention, an electronic device is provided which includes at least one organic light-emitting device according to any embodiment described herein, preferably the electronic device includes an organic light-emitting diode according to one of the embodiments described herein. More preferably the electronic device is a display device.

[0660] The embodiments will be described in more detail below with reference to the examples. However, this disclosure is not limited to the following embodiments. Next, the exemplary embodiments will be described in detail.

[0661] [Description of the drawing] The aforementioned components, as well as the components used in accordance with the present invention in the claimed components and described embodiments, are not subject to any special exceptions, as the selection criteria known in the relevant art can be applied without limitation to their size, shape, material selection, and technical concept.

[0662] Additional details, features, and advantages relating to the subject matter of the present invention are disclosed in the dependent claims and the following description of the drawings, which illustrate preferred embodiments of the present invention. However, none of the embodiments necessarily represent the entire scope of the invention, and therefore, the scope of the invention should be interpreted by referring to the claims and this specification. It should be understood that the above general description and the following detailed description are all illustrative and descriptive and are intended to further illustrate the scope described in the claims.

[0663] Figure 1 is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment; Figure 2 is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment; Figure 3 is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment; Figure 4 is a schematic cross-sectional view of an OLED according to an exemplary embodiment.

[0664] Figure 5 is a schematic cross-sectional view of an OLED according to an exemplary embodiment.

[0665] Figure 6 is a schematic cross-sectional view of an OLED according to an exemplary embodiment.

[0666] Figure 7 is a schematic cross-sectional view of an OLED according to an exemplary embodiment.

[0667] The following will provide a detailed explanation with reference to the drawings. However, this disclosure is not limited to the drawings shown below.

[0668] Where it is referred to herein that a first element is formed or positioned "on" or "onto" a second element, the first element may be positioned directly on the second element, or one or more other elements may be positioned between them. Where it is referred to that a first element is formed or positioned "directly on" or "directly onto" a second element, no other elements are positioned between them.

[0669] Figure 1 is a schematic cross-sectional view of an exemplary embodiment of an organic electronic device 100. The organic electronic device 100 includes a substrate 110, an anode layer 120, and an organic semiconductor layer 131 which may contain a compound of formula (I). The organic semiconductor layer 131 is disposed on the anode layer 120. A cathode layer 190 is disposed on the organic semiconductor layer 131.

[0670] Figure 2 is a schematic cross-sectional view of an organic electronic device 100 according to an exemplary embodiment. The organic electronic device 100 includes a substrate 110, an anode layer 120, and a hole injection layer (HIL) 130 which may contain a compound of formula (I). The HIL 130 is located on the anode layer 120. A photoactive layer (PAL) 170 and a cathode layer 190 are located on the HIL 130.

[0671] Figure 3 is a schematic cross-sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment. The OLED 100 includes a substrate 110, an anode layer 120, and a hole injection layer (HIL) 130 which may contain a compound of formula (I). The HIL 130 is located on the anode layer 120. A hole transport layer (HTL) 140, an emissive layer (EML) 150, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180, and a cathode layer 190 are located on the HIL 130. Optionally, an electron transport layer stack (ETL) can be used instead of a single electron transport layer 160.

[0672] Figure 4 is a schematic cross-sectional view of an OLED 100 according to another exemplary embodiment. Unlike Figure 3, the OLED 100 in Figure 4 includes an electron-blocking layer (EBL) 145 and a hole-blocking layer (HBL) 155.

[0673] Referring to Figure 4, the OLED 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 which may contain a compound of formula (I), a hole transport layer (HTL) 140, an electron barrier layer (EBL) 145, an emissive layer (EML) 150, a hole barrier layer (HBL) 155, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180, and a cathode layer 190.

[0674] Figure 5 is a schematic cross-sectional view of an organic electronic device 100 according to an exemplary embodiment. The organic electronic device 100 includes a substrate 110, an anode layer 120 comprising a first anode sublayer 121, a second anode sublayer 122, and a third anode sublayer 123, and a hole injection layer (HIL) 130. The HIL 130 is disposed on the anode layer 120. A hole transport layer (HTL) 140, a first light-emitting layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, and a cathode layer 190 are disposed on the HIL 130. The hole injection layer 130 may contain a compound of formula (I).

[0675] Figure 6 is a schematic cross-sectional view of an exemplary embodiment of an organic electronic device 100. The organic electronic device 100 includes a substrate 110, an anode layer 120 comprising a first anode sublayer 121, a second anode sublayer 122, and a third anode sublayer 123, and a hole injection layer (HIL) 130. The HIL 130 is located on the anode layer 120. On the HIL 130 are a hole transport layer (HTL) 140, an electron barrier layer (EBL) 145, a first light-emitting layer (EML) 150, a hole barrier layer (HBL) 155, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180, and a cathode layer 190. The hole injection layer 130 may contain a compound of formula (I).

[0676] Figure 7 is a schematic cross-sectional view of an organic electronic device 100 according to an exemplary embodiment. The organic electronic device 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130, a first hole transport layer (HTL) 140, a first electron barrier layer (EBL1) 145, a first light-emitting layer (EML1) 150, an optional first hole barrier layer (HBL) 155, a first electron transport layer (ETL1) 160, an n-type charge generation layer (n-CGL) 185, a p-type charge generation layer (p-GCL) 135 which may contain a compound of formula (I), a second hole transport layer (HTL2) 141, a second electron barrier layer (EBL2) 146, a second light-emitting layer (EML2) 151, an optional second hole barrier layer (HBL2) 156, a second electron transport layer (ETL2) 161, an electron injection layer (EIL) 180, and a cathode layer 190. Furthermore, HIL may contain the compound of formula (I). The hole injection layer may contain the compound of formula (I). The anode layer may include a first anode sublayer, a second anode sublayer, and an optional third anode sublayer.

[0677] Although not shown in Figures 1 to 7, a capping layer and / or sealing layer may be formed on the cathode layer 190 to encapsulate the organic electronic device 100. Furthermore, various other modifications may be made.

[0678] One or more exemplary embodiments are described below in detail with reference to the following examples. However, these examples are not intended to limit the purpose and scope of the one or more exemplary embodiments.

[0679] [Detailed explanation] [Synthesis]

[0680] [ka]

[0681] (Intermediate B) In a three-necked round-bottom flask equipped with a reflux condenser, dropping funnel, and septum, 2 equivalents of 100% sodium hydride were suspended in dry dimethoxyethane (DME) and cooled to below 10°C using an ice bath under an inert gas atmosphere. 1 equivalent of malon nitrile solution was added dropwise to the dry DME, and the mixture was stirred at 0-10°C for 15 minutes. Then, 1 equivalent of compound A was added in solid form, and the mixture was stirred at 0°C for 15 minutes and then overnight at room temperature. After the reaction was complete, the mixture was poured into an ice water mixture and acidified with hydrochloric acid. The precipitate was washed several times with water, and a purity of over 95% was obtained by HPLC.

[0682] (Intermediate C) In a three-necked round-bottom flask equipped with a reflux condenser, dropping funnel, and septum, 4 equivalents of 100% sodium hydride were suspended in dry DME and cooled to below 10°C using an ice bath under an inert gas atmosphere. 1.9 equivalents of a solution of compound B were added dropwise to anhydrous DME, and the mixture was stirred at 0–10°C for 15 minutes. Then, 1 equivalent of intermediate B and tetrakis(triphenylphosphine)palladium(O) were added in solid form, and the mixture was stirred at 0°C for 15 minutes, at room temperature for 15 minutes, and overnight under reflux. After the reaction was complete, the mixture was poured into an ice water mixture and acidified with hydrochloric acid. The aqueous phase was extracted twice with ethyl acetate, and the organic phase was washed three times with semi-concentrated saline, then with concentrated saline, and dried over sodium sulfate. After solvent removal, the product was purified by column chromatography, and the product had a purity of over 98% by HPLC.

[0683] [ka]

[0684] (Intermediate B1) To a solution of aryl halide (compound A) dissolved in DMF, 1.2 equivalents of potassium carbonate were added. After adding 1.2 equivalents of t-butylcyanoacetic acid dropwise, the mixture was stirred at 50°C for 3 days. Solid by-products were removed by filtration, and the filtrate was evaporated to dryness. The crude product was ground twice with DCM (room temperature, 2 hours), and the precipitated product was collected on frit and washed three times with DCM. The final product was vacuum-dried overnight.

[0685] (Intermediate B2) In a three-necked round-bottom flask equipped with a reflux condenser, dropping funnel, and septum, 2 equivalents of 100% sodium hydride were suspended in dry dimethoxyethane (DME) and cooled to below 10°C using an ice bath under an inert gas atmosphere. 1 equivalent of malon nitrile solution was added dropwise to the dry DME, and the mixture was stirred at 0–10°C for 15 minutes. Then, 1 equivalent of compound B1 was added in solid form, and the mixture was stirred at 0°C for 15 minutes and overnight at room temperature. After the reaction was complete, the mixture was poured into an ice water mixture and acidified with hydrochloric acid. The precipitate was washed several times with water and DCM, and a purity of over 95% was obtained by HPLC.

[0686] (Intermediate B3) Intermediate B2 (5 g) was dissolved in dioxane (10 mL) in a pressure tube, and 4 M hydrochloric acid solution (2 equivalents) was added to the dioxane. The tube was sealed and stirred overnight at 100°C. After cooling to room temperature, the mixture was poured into water (40 mL) and extracted three times with ethyl acetate (30 mL). The integrated organic phase was washed with water (50 mL), 0.5 M sodium bicarbonate solution (50 mL), and saline solution (50 mL). After drying over sodium sulfate and evaporating the solvent, the compound was purified by silica filtration.

[0687] (Intermediate C1) In a three-necked round-bottom flask equipped with a reflux condenser, dropping funnel, and septum, 3 equivalents of 100% sodium hydride were suspended in dry dimethoxyethane (DME) and cooled to below 10°C using an ice bath under an inert gas atmosphere. After adding the solution of intermediate B3 dropwise to the dry DME, the mixture was stirred at 0–10°C for 15 minutes. Then, 1.2 equivalents of compound C were added in solid form all at once, and the mixture was stirred at 0°C for 15 minutes and then overnight at room temperature. After the reaction was complete, the mixture was poured into an ice water mixture and acidified with hydrochloric acid. The precipitate was washed with water, extracted with ethyl acetate, filtered through silica, and precipitated with DCM. After column chromatography, the target compound usually had a purity of over 95% by HPLC.

[0688] Compounds (I), (IVa), (IVb) Before acidification, intermediate C was converted to a potassium salt by suspension in a potassium carbonate solution. The salt was then extracted with ethyl acetate, and the solution was concentrated under vacuum. The potassium salt was precipitated by dropwise addition of the concentrated solution to an excess of n-hexane, and the solution was filtered. After drying under vacuum, the potassium salt was suspended in dry dichloromethane (DCM) under an inert gas atmosphere, and 1.25 equivalents of (bis(trifluoroacetoxy)iodo)benzene (PIFA) were added in a single addition. The mixture was stirred overnight at room temperature in the dark. The product was filtered, washed three times with DCM, and then purified by stirring in refluxed chloroform at room temperature to obtain a yellow powder. The product may be further purified by methods known in the art (e.g., US2005121667A1).

[0689] (Calculated HOMO energy) HOMO and LUMO were calculated using the program packages ORCA V5.0.3 (Max Planck Institute fur Kohlenforschung, Kaiser Wilhelm Platz 1, 45470, Muelheim / Ruhr, Germany) and WEASEL 1.9.2 (FAccTs GmbH, Rolandstrasse 67, 50677 Koln, Germany). The HOMO and LUMO energy levels of the molecular structure were determined by applying the hybrid functional B3LYP and the def2-tzvp basis set to the optimized geometric structure obtained by applying the composite method HF-3c in the gas phase. All calculations were performed in the gas phase. When multiple conformations are possible, the conformation with the lowest total energy is selected.

[0690] (Dipole moment) The dipole moment of the molecular structure was determined by applying the hybrid functional B3LYP and the def2-tzvp basis set to the optimized geometric structure obtained by applying the combined method HF-3c in the gas phase. All calculations were performed in the gas phase. When multiple conformations are possible, the conformation with the lowest total energy is selected.

[0691] Table I shows the LUMO data for comparative compound C1 and compounds K1-K365 of the present invention.

[0692] [Table 2]

[0693] JPEG2026530313000181.jpg246169

[0694] JPEG2026530313000182.jpg246169

[0695] JPEG2026530313000183.jpg246169

[0696] JPEG2026530313000184.jpg255168

[0697] JPEG2026530313000185.jpg251169

[0698] JPEG2026530313000186.jpg249169

[0699] JPEG2026530313000187.jpg255161

[0700] JPEG2026530313000188.jpg246169

[0701] JPEG2026530313000189.jpg246169

[0702] JPEG2026530313000190.jpg246169

[0703] JPEG2026530313000191.jpg246169

[0704] JPEG2026530313000192.jpg255163

[0705] JPEG2026530313000193.jpg248169

[0706] JPEG2026530313000194.jpg246169

[0707] JPEG2026530313000195.jpg245169

[0708] JPEG2026530313000196.jpg246169

[0709] JPEG2026530313000197.jpg249169

[0710] JPEG2026530313000198.jpg252169

[0711] JPEG2026530313000199.jpg244169

[0712] JPEG2026530313000200.jpg255162

[0713] JPEG2026530313000201.jpg250169

[0714] JPEG2026530313000202.jpg250169

[0715] JPEG2026530313000203.jpg246169

[0716] JPEG2026530313000204.jpg254169

[0717] JPEG2026530313000205.jpg155169

[0718] (Melting point) The melting point (Tm) is determined from the DSC curve obtained from the TGA-DSC measurement described above, or as the peak temperature obtained from a separate DSC measurement (Mettler Toledo DSC822e, heated at a heating rate of 10 K / min from room temperature until melting is complete under a stream of pure nitrogen. 4-6 mg of the sample is placed in a 40 μM Mettler Toledo aluminum dish with a lid, and a hole of less than 1 mm is made in the lid).

[0719] (Glass transition temperature) The glass transition temperature (Tg) is measured using a Mettler Toledo DSC 822e differential scanning calorimeter under nitrogen at a heating rate of 10 K / min, as specified in DIN EN ISO 11357 issued in March 2010. According to one embodiment, the glass transition temperature Tg is >100°C, preferably >110°C, and more preferably >120°C.

[0720] (Thermogravimetric analysis) The term "TGA 5%" refers to the temperature at which a 5% weight loss occurs during thermogravimetric analysis, and is measured in °C.

[0721] The 5% TGA value may also be determined by heating a 9-11 mg sample in a thermogravimetric analyzer at a heating rate of 10 K / min in an open 100 μL aluminum dish, under a nitrogen gas flow rate of 20 mL / min in the equilibrium region and 30 mL / min in the oven region.

[0722] The TGA 5% value may provide an indirect indicator of the volatility and / or decomposition temperature of a compound. As a first approximation, a higher TGA 5% value indicates lower volatility and / or a higher decomposition temperature of the compound.

[0723] According to one embodiment, the TGA 5% value of the compound of formula (I) is selected in the range of ≥280°C and ≤420°C; preferably in the range of ≥290°C and ≤410°C, and more preferably in the range of ≥295°C and ≤410°C. TGA 5% values ​​within this range represent sufficiently low volatility to allow for precise control of deposition and sufficiently high volatility to limit thermal stress during evaporation, respectively.

[0724] (Rate start temperature) Rate start temperature (T RO ) is measured by loading 100 mg of the compound into a VTE source. As the VTE source, a point source for organic materials supplied by Kurt J. Lesker Company (www.lesker.com) or CreaPhys GmbH (http: / / www.creaphys.com) may be used. The VTE source is 10 -5The VTE source is heated at a constant rate of 15 K / min under a pressure of less than mbar, and its internal temperature is measured with a thermocouple. Compound deposition is detected by a QCM detector, which detects the deposition of the compound on the quartz crystal of the detector. The deposition rate on the quartz crystal is measured in angstroms per second. To determine the rate onset temperature, the deposition rate is plotted against the VTE source temperature. Rate onset is the temperature at which significant deposition occurs on the QCM detector. To obtain accurate results, the VTE source is heated and cooled three times, and only the results from the second and third cycles are used to determine the rate onset temperature.

[0725] To achieve good control over the deposition rate of organic compounds, the rate start temperature may be in the range of 170-280°C. If the rate start temperature is below 170°C, deposition may be too fast and difficult to control. If the reaction start temperature exceeds 280°C, the deposition rate may be too low, resulting in a decrease in cycle time and potentially causing decomposition of the organic compound in the VTE source due to prolonged exposure to high temperatures.

[0726] The rate onset temperature is an indirect indicator of a compound's volatility. The higher the rate onset temperature, the lower the volatility of the compound.

[0727] (Dipole moment) The dipole moment of a molecule containing N atoms

[0728]

number

[0729] It is given by the following equation:

[0730]

number

[0731]

number

[0732] During the ceremony,

[0733]

number

[0734] And,

[0735]

number

[0736] is the partial charge and position of atom i in the molecule. The geometry of the molecular structure is optimized using the HF-3c composite method in the gas phase (program packages ORCA V5.0.3 (Max Planck Institute fur Kohlenforschung, Kaiser Wilhelm Platz 1, 45470, Muelheim / Ruhr, Germany) and WEASEL 1.9.2 ((FAccTs GmbH, Rolandstrasse 67, 50677 Koln, Germany)). If multiple conformations are possible, the conformation with the lowest total energy is selected to determine the molecular structure and electronic parameters.

[0737] [General procedure for manufacturing OLEDs (where the organic semiconductor layer is a hole injection layer (HIL))] An OLED device may be manufactured by the following method: A glass substrate having an anode layer comprising a first anode sublayer of 10 nm ITO, a second anode sublayer of 120 nm Ag, and a third anode sublayer of 8 nm ITO was cut to a size of 100 mm × 100 mm × 0.7 mm and ultrasonically cleaned with water for 60 minutes, followed by isopropanol for 20 minutes. The liquid film was removed in a nitrogen stream, and then plasma treatment was performed to prepare the anode layer. The plasma treatment was carried out in an atmosphere containing 97.6 volume% nitrogen and 2.4 volume% oxygen.

[0738] Next, N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine (N-5) was selected as the hole transport matrix compound. A hole injection layer (HIL) with a thickness of 10 nm was formed by vacuum deposition using 8 wt% of a compound selected from the K1 to K365 compounds of the present invention as a dopant.

[0739] Next, N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine (N-5) was vacuum deposited to form a hole transport layer (HTL) with a thickness of 128 nm.

[0740] Next, N,N-di([1,1'-biphenyl]-4-yl)-3'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine(N-3) was vacuum deposited onto the HTL to form an electron barrier layer (EBL) with a thickness of 5 nm.

[0741] Next, a 20 nm thick luminescent layer (EML) is formed on the EBL by co-depositing 99 volume% of dibenzofuran, 7-(phenyl-2,3,4,5,6-d)-1-[10-(phenyl-2,3,4,5,6-d)-9-anthracenyl][2457172-82-4] as the EML host, and 1 volume% of 5H,9H-[1]benzothieno[2',3':5,6][1,4]azabolino[2,3,4-kl]phenazavolin, 2,7,11-tris(1,1-dimethylethyl)-5,9-bis[4-(1,1-dimethylethyl)phenyl][2482607-57-6] as the blue dopant.

[0742] Next, a 5 nm thick hole-blocking layer is formed on the EML by depositing the compound 4-([1,1'-biphenyl]-4-yl)-6-(3'-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine (N-6).

[0743] Next, an electron transport layer with a thickness of 31 nm is formed on the HBL by co-depositing the compound 2-(2',6'-diphenyl-[1,1':4',1''-terphenyl]-4-yl)-4-phenyl-6-(3-(pyridine-4-yl)phenyl)-1,3,5-triazine(N-7) and LiQ in a 50:50 weight percentage ratio.

[0744] Next, set Yb to 10 -7 The electrons were evaporated at a rate of 0.01 to 1 Å / s in mbar to form a 2 nm thick electron injection layer (EIL) on the electron transport layer.

[0745] Ag / Mg (1.8% by weight) 10 -7 A cathode with a thickness of 13 nm was formed by evaporation at a rate of 0.01 to 1 Å / s in mbar.

[0746] Next, N-({[1,1-'biphenyl]-4-yl)-9,9,dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine) was vacuum deposited onto the cathode layer to form a coating layer with a thickness of 75 nm.

[0747] [Table 3]

[0748] JPEG2026530313000212.jpg195169

[0749] [General procedure for manufacturing OLED devices (OLED device including a p-type charge generation layer containing the compound of the present invention)] An OLED device may be manufactured by the following method: A glass substrate having an anode layer comprising a first anode sublayer of 10 nm ITO, a second anode sublayer of 120 nm Ag, and a third anode sublayer of 8 nm ITO was cut to a size of 100 mm × 100 mm × 0.7 mm and ultrasonically cleaned with water for 60 minutes, followed by isopropanol for 20 minutes. The liquid film was removed in a nitrogen stream, and then plasma treatment was performed to prepare the anode layer. The plasma treatment was carried out in an atmosphere containing 97.6 volume% nitrogen and 2.4 volume% oxygen.

[0750] Next, as the first hole transport matrix compound, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine (N-1) was vacuum deposited in 2 wt% of 4,4',4''-((1E,1'E,1''E)-cyclopropane-1,2,3-triylidenetris(cyanomethanylylidene))tris-(2,3,5,6-tetrafluorobenzonitrile) (N-2) to form a 10 nm thick hole implantation layer (pHIL).

[0751] Next, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine (N-1) was vacuum deposited to form a first hole transport layer with a thickness of 29 nm.

[0752] Next, N,N-di([1,1'-biphenyl]-4-yl)-3'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine(N-3) was vacuum deposited onto the HTL to form an electron barrier layer (EBL) with a thickness of 5 nm.

[0753] Next, a first luminescent layer (EML1) with a thickness of 19 nm is formed on EBL1 by co-depositing 99% by volume of dibenzofuran, 7-(phenyl-2,3,4,5,6-d)-1-[10-(phenyl-2,3,4,5,6-d)-9-anthracenyl][2457172-82-4] as the EML host, and 1% by volume of 5H,9H-[1]benzothieno[2',3':5,6][1,4]azabolino[2,3,4-kl]phenazavolin, and 2,7,11-tris(1,1-dimethylethyl)-5,9-bis[4-(1,1-dimethylethyl)phenyl][2482607-57-6] as the blue dopant.

[0754] Next, a 15 nm thick first electron transport layer (ETL1) is formed on the first light-emitting layer by depositing 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline](N-4).

[0755] Next, a first n-type charge generation layer (n-CGL1) with a thickness of 7.5 nm is formed on the first electron transport layer (ETL1) by co-depositing 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline](N-4) and 2 volume% of Yb or 1 volume% of Li.

[0756] Next, a first p-type charge generation layer (p-CGL) with a thickness of 10 nm is formed on the first n-type CGL by co-depositing 90 volume percent of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine (N-5) with 10 volume percent of compounds K1 to K365 of the present invention as a dopant.

[0757] Next, a second hole transport layer with a thickness of 43 nm is formed on the first p-type CGL by depositing N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine (N-5).

[0758] Next, a second electron-barrier layer with a thickness of 5 nm is formed on the second hole transport layer by depositing N,N-di([1,1'-biphenyl]-4-yl)-3'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine(N-3).

[0759] Next, a second luminescent layer (EML2) with a thickness of 19 nm is formed on EBL1 by co-depositing 99% by volume of dibenzofuran, 7-(phenyl-2,3,4,5,6-d)-1-[10-(phenyl-2,3,4,5,6-d)-9-anthracenyl][2457172-82-4] as the EML host, and 1% by volume of 5H,9H-[1]benzothieno[2',3':5,6][1,4]azabolino[2,3,4-kl]phenazavolin, and 2,7,11-tris(1,1-dimethylethyl)-5,9-bis[4-(1,1-dimethylethyl)phenyl][2482607-57-6] as the blue dopant.

[0760] Next, a first hole-blocking layer (HBL1) with a thickness of 5 nm is formed on EML2 by depositing the compound 4-([1,1'-biphenyl]-4-yl)-6-(3'-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine (N-8).

[0761] Next, a second electron transport layer (ETL2) with a thickness of 31 nm is formed on the HBL by co-depositing the compound 6,6'-(naphthalene-1,2-diylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine)(N-9) and LiQ in a 50:50 weight percentage ratio.

[0762] Next, set Yb to 10 -7 The material was evaporated at a rate of 0.01 to 1 Å / s in mbar, forming an electron injection layer (EIL) with a thickness of 1.3 nm on the electron transport layer.

[0763] Ag / Mg (1.8% by weight) -7A cathode with a thickness of 13 nm was formed by evaporation at a rate of 0.01 to 1 Å / s in mbar.

[0764] Next, N-({[1,1-'biphenyl]-4-yl)-9,9,dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine) was vacuum deposited onto the cathode layer to form a coating layer with a thickness of 75 nm.

[0765] [General procedure for manufacturing OLEDs by solution processing (where the organic semiconductor layer is a hole injection layer (HIL))] For bottom light-emitting devices, see Table III. Glass substrate with 90nm ITO (15Ω / cm 2 The material (available from Corning Co.) was cut to a size of 50 mm x 50 mm x 0.7 mm and ultrasonically cleaned with isopropyl alcohol for 5 minutes, followed by 5 minutes with pure water. The anode layer was prepared by cleaning again with UV ozone for 30 minutes.

[0766] Next, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine [1242056-42-3] was deposited as a hole transport matrix compound by solution treatment using 1% by weight of the compounds of the present invention shown in Table III, or 1% by weight of the comparative compound dipyradino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonite (CNHAT; [105598-27-4]) as a p-dopant, to form a 50 nm thick hole implantation layer (HIL).

[0767] Next, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine[1242056-42-3] was vacuum deposited to form a hole transport layer (HTL) with a thickness of 88 nm.

[0768] Next, N-([1,1'-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenylsilyl)phenyl)-9H-fluoren-2-amine[1613079-70-1] was vacuum deposited onto the HTL to form an electron barrier layer (EBL) with a thickness of 5 nm.

[0769] Next, 97 volume% of H09 (Sun Fine Chemicals, Korea) as the EML host and 3 volume% of BD200 (Sun Fine Chemicals, Korea) as the fluorescent blue dopant were co-deposited onto the EBL to form a 20 nm thick blue light-emitting layer (EML).

[0770] Next, a 5 nm thick hole-blocking layer (HBL) was formed by depositing 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine[1955543-57-3] on the emissive layer EML.

[0771] Next, an electron transport layer (ETL) with a thickness of 31 nm was formed on the hole barrier layer by depositing 50 volume% of 4'-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalene-1-yl)-[1,1'-biphenyl]-4-carbonitrili[2032421-37-5] and 50 volume% of LiQ.

[0772] Next, Yb was deposited on the ETL to form an electron injection layer (EIL) with a thickness of 2 nm.

[0773] Next, add Al to 10 -7 The material was evaporated at a rate of 0.01 to 1 Å / s in mbar, and a 100 nm thick cathode layer was formed on the electron injection layer.

[0774] To evaluate the performance of the invention compared to prior art, the current efficiency at 20°C is measured. The current-voltage characteristics are determined by applying a voltage V and measuring the current mA flowing through the device under test using a Kiesley 2635 source measure unit. The voltage applied to the device is varied in 0.1V increments from 0V to 10V. Similarly, the luminance-voltage characteristics and CIE coordinates are measured for each voltage value using an Instrument Systems CAS-140CT array spectrophotometer (calibrated by the German accreditation body (DAkkS)) in cd / m². 2 It is determined by measuring the brightness. 15mA / cm 2 The cd / A efficiency in this case is determined by interpolating the luminance-voltage characteristics and the current-voltage characteristics, respectively.

[0775] In bottom-emitting devices, luminescence primarily exhibits a Lambertian distribution and is quantified by a percentage value of the external quantum efficiency (EQE). To determine the EQE efficiency in percentage, a calibrated photodiode is used to obtain a value of 10 mA / cm². 2 Measure the optical output of the device.

[0776] In the upper light-emitting device, the emission is forward-directed, exhibits a non-Lambertian distribution, and is highly dependent on the microcavity. Therefore, the efficiency EQE can be higher compared to the lower light-emitting device. To determine the efficiency EQE in percentage, a calibrated photodiode was used to measure 10 mA / cm². 2 Measure the optical output of the device.

[0777] The device lifetime LT is calculated under ambient conditions (20°C) and 10 mA / cm². 2 or 30mA / cm 2 Measurements are taken using a Keithley 2400 source meter and recorded in time units.

[0778] The device brightness is measured using a calibrated photodiode. The lifetime LT is defined as the time it takes for the device brightness to decrease to 97% of its initial value.

[0779] The increase in operating voltage ΔU is used as an indicator of the stability of the device's operating voltage. This increase is determined during LT measurement by subtracting the operating voltage after 1 hour of device operation from the operating voltage after 100 hours.

[0780] ΔU=[U(100 hours)-U(1 hour)] The smaller the value of ΔU, the better the operating voltage stability.

[0781] The specific combinations of elements and features in the detailed embodiments described above are merely examples, and the interchangeability of these teachings and their substitution with other teachings are expressly assumed in this specification and in the patents / applications incorporated by reference. As those skilled in the art will recognize, it is assumed that a person of ordinary skill in the art can easily conceive of various variations, modifications, and other embodiments of the content described herein without departing from the spirit and scope of the claimed invention. Thus, the above description is illustrative and not intended to limit. In the claims, the word “comprising” does not exclude other elements or steps, and the indefinite article “a” or “an” does not exclude the plural. The mere fact that certain means are described in different dependent claims does not indicate that combinations of these means cannot be advantageously utilized. The scope of the invention is defined in the following claims and their equivalents. Furthermore, the reference symbols used in the specification and claims do not limit the scope of the claimed invention.

[0782] [Table 4]

[0783] The comparison device (Comparative Example 1) exhibits an operating voltage of over 10V.

[0784] The device of the present invention (Example 1) exhibits an operating voltage of 7.0V, which is therefore a much lower operating voltage than the comparative device (Comparative Example 1).

[0785] Reducing the operating voltage may be important for the battery life of organic electronic devices, especially mobile devices.

[0786] Furthermore, the device of the present invention (Example 1) exhibits an external quantum efficiency (EQE) of 11.2% and a current efficiency (Ceff) of 96 cd / A. Therefore, the device of the present invention (Example 1) exhibits both good external quantum efficiency and current efficiency.

[0787] High efficiencies, such as external quantum efficiency and current efficiency, can contribute to reduced power consumption and improved battery life, particularly in mobile devices.

[0788] Furthermore, the device of the present invention (Example 1) exhibits a lifespan of 2 hours (LT97). Therefore, the device of the present invention (Example 1) exhibits a good lifespan.

[0789] The device of the present invention (Example 1) exhibits a voltage increase of 2.15V over time. Therefore, the device of the present invention (Example 1) exhibits a good voltage increase over time.

[0790] Long lifespan and low voltage rise over time can lead to improved long-term stability of electronic devices. [Brief explanation of the drawing]

[0791] [Figure 1] Figure 1 is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment. [Figure 2] Figure 2 is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment. [Figure 3] Figure 3 is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment. [Figure 4] Figure 4 is a schematic cross-sectional view of an OLED according to an exemplary embodiment. [Figure 5] Figure 5 is a schematic cross-sectional view of an OLED according to an exemplary embodiment. [Figure 6] Figure 6 is a schematic cross-sectional view of an OLED according to an exemplary embodiment. [Figure 7] Figure 7 is a schematic cross-sectional view of an OLED according to an exemplary embodiment.

Claims

1. Compound of formula (I): 【Chemistry 1】 [In formula (I), A １ This is expressed by equation (II), 【Chemistry 2】 In formula (II), B １ This is expressed by equation (III), 【Transformation 3】 Here, the asterisk "*" indicates the joining position. X １ CR １ or selected from N; X ２ CR ２ or selected from N; X ３ CR ３ or selected from N; X ４ is selected from CR ４ or N; X ５ CR ５ or selected from N; R １ , R ２ , R ３ , R ４ , and, R ５ Independently, H, D, F, Cl, CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl or fully fluorinated C １ ~C ８ Alkyl, partially fluorinated C １ ~C ８ Alkoxy or fully fluorinated C １ ~C ８ Alkoxy, substituted, or unsubstituted C ６ ~C ４０ Aryl, substituted, or unsubstituted C ３ ~C ４０ Heteroaryl, SF ５ Selected from the group including, Here, R １ , R ２ , R ３ , R ４ , and, R ５ The one or more substituents above are independent, D, F, Cl, CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl or fully fluorinated C １ ~C ８ Alkyl, partially fluorinated C １ ~C ８ Alkoxy or fully fluorinated C １ ~C ８ Alkoxy, SF ５ Selected from the group including; Here, optionally, X １ , X ２ , X ３ , X ４ , and, X ５ At least one, at least two, or at least three of these are independently, CF, CCl, CSF ５ CCN, CCF ３ CC ｍ F ２ｍ＋１ (m is 1 to 8), or CC ｍ F （２ｍ＋１）－ｔ H ｔ (m = 1 to 8, and t = 1 to 2m), COCF ３ COC ｍ F ２ｍ＋１ (m is 1 to 8), or COC ｍ F （２ｍ＋１）－ｔ H ｔ (m = 1 to 8, and t = 1 to 2m), substituted or unsubstituted C-C ６ From Arley to C-C ４０ Aryl, substituted, or unsubstituted C-C ３ From heteroaryl to C-C ４０ Heteroaryl, Selected from; and / or, X １ , X ２ , X ３ , X ４ , and, X ５ At least one of is selected from N; and / or, X １ ~X ５ At least one of them is N, and X １ ~X ５ At least one or at least two of them independently, CF, CCl, CSF ５ , CCN, CCF ３ , CC ｍ F ２ｍ＋１ (m is 1 to 8), CC ｍ F （２ｍ＋１）－ｔ H ｔ (m is 1 to 8, t = 1 to 2m), OCCF ３ , OCC ｍ F ２ｍ＋１ (m is 1 to 8), or OCC ｍ F （２ｍ＋１）－ｔ H ｔ (m = 1 to 8, t = 1 to 2m), substituted or unsubstituted C-C ６ aryl to C-C ４０ aryl, substituted or unsubstituted C-C ３ heteroaryl to C-C ４０ heteroaryl, Selected from; R ａ , R ｂ , R ｃ to R ｄ are independently H, D, F, Cl, CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl or fully fluorinated C １ ~C ８ Alkyl, partially fluorinated C １ ~C ８ Alkoxy or fully fluorinated C １ ~C ８ Alkoxy, SF ５ Selected from the group including; Here, R ａ , R ｂ , R ｃ , and, R ｄ At least one, at least two, or at least three of these are independently, F, Cl, CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl or fully fluorinated C １ ~C ８ Alkyl, partially fluorinated C １ ~C ８ Alkoxy or fully fluorinated C １ ~C ８ Alkoxy, SF ５ Selected from the group including; and, Optionally, the following compounds E1 to E5: 【Chemistry 4】 [This is excluded.]

2. Compound (I) is excluded, and here, R １ , R ２ , R ３ , R ４ , and, R ５ Independently, H, D, F, Cl, CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl or fully fluorinated C １ ~C ８ Alkyl, Preferably, F, Cl, C test, CF ３ , partially fluorinated C １ ~C ８ Alkyl or fully fluorinated C １ ~C ８ Selected from the group including alkyl groups; X １ , X ２ , X ３ , X ４ , and, X ５ At least two of are independently selected from CH, CD, or N; and, Here, R ａ and R ｄ is selected from F, and R ｂ and R ｃ is selected from F or CN; or, R ａ and R ｄ is selected from F, and R ｂ and R ｃ is selected from CN; or, R ａ and R ｄ is selected from F, and R ｂ and R ｃ is selected from F; or, R ａ and R ｄ is selected from F or CN, and R ｂ and R ｃ is selected from F; or, R ａ and R ｄ is selected from CN, and R ｂ and R ｃ is selected from F; and / or, Optionally, the following compounds E1 to E5: 【Transformation 5】 is excluded; and / or, Optionally, R １ , R ２ , R ３ , R ４ , and, R ５ Those that are halogens are excluded. The compound of formula (I) as described in claim 1.

3. Compound (I) is excluded, and here, R １ , R ２ , R ３ , R ４ , and, R ５ Independently, F, Cl, CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl or fully fluorinated C １ ~C ８ Selected from alkyl groups; X １ , X ２ , X ３ , X ４ , and, X ５ At least two of are independently selected from CH, CD, or N; and, R ａ , R ｂ , R ｃ , R ｄ These two are independently selected from F or CN, and R ａ , R ｂ , R ｃ , R ｄ The remaining two are selected from F. A compound of formula (I) according to claim 1 or 2.

4. Compound (I) is excluded, and here, R １ , R ２ , R ３ , R ４ , and, R ５ Independently, F, Cl, CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl or fully fluorinated C １ ~C ８ Selected from alkyl groups; X １ , X ２ , X ３ , X ４ , and, X ５ At least two of are independently selected from CH, CD, or N; and, R ａ , R ｂ , R ｃ , R ｄ These two are independently F, Cl, CN, or CF ３ Selected from, preferably selected from F or CN, A compound of formula (I) according to any one of claims 1 to 3.

5. Compound (I) is excluded, and here, R ａ and R ｄ is selected from F, and R ｂ and R ｃ is selected from F or CN; or, R ａ and R ｄ is selected from F, and R ｂ and R ｃ is selected from CN; or, R ａ and R ｄ is selected from F, and R ｂ and R ｃ is selected from F; or, R ａ and R ｄ is selected from F or CN, and R ｂ and R ｃ is selected from F; or, R ａ and R ｄ is selected from CN, and R ｂ and R ｃ It is selected from F. A compound of formula (I) according to any one of claims 1 to 4.

6. The compound of formula (I) is of formula (IVa) or formula (IVb): 【Transformation 6】 or 【Transformation 7】 Represented by, A compound of formula (I) according to any one of claims 1 to 5.

7. The compounds of formula (I) are formulas (VA) to (VH) and (VJ) to (VR): 【Transformation 8】 Represented by, A compound of formula (I) according to any one of claims 1 to 6.

8. The above formulas (I), (IVa), (IVb), (VA) to (VH), and (VJ) to (VR) contain at least 4 CN groups, preferably 4 to 10 CN groups, more preferably 4 to 9 CN groups, more preferably 5 to 9 CN groups, more preferably 6 to 8 CN groups, more preferably 5 to 7 CN groups, in addition preferably 5 to 9 CN groups, and more preferably 6 to 9 CN groups. A compound of formula (I) according to any one of claims 1 to 7.

9. R ａ , R ｂ , R ｃ , and, R ｄ At least one or at least two of are independently selected from H or D. A compound of formula (I) according to any one of claims 1 to 8.

10. R ａ , R ｂ , R ｃ , and, R ｄ At least one of them is selected from CN. A compound of formula (I) according to any one of claims 1 to 9.

11. R １ , R ２ , R ３ , R ４ , and, R ５ Independently, H, D, CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl or fully fluorinated C １ ~C ８ Alkyl, substituted, or unsubstituted C ６ ~C ４０ Aryl, substituted, or unsubstituted C ３ ~C ４０ Heteroaryl, SF ５ Selected from, Here, R １ , R ２ , R ３ , R ４ , and, R ５ The one or more substituents above are independent, D, CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl, fully fluorinated C １ ~C ８ Alkyl, or SF ５ Selected from; or, R １ , R ２ , R ３ , R ４ , and, R ５ Independently, H, D, CN, CF ３ Selected from, halogen is sp ２ It is assumed that it is not directly bonded to carbon. Furthermore, partially fluorinated C １ ~C ８ Alkyl or fully fluorinated C １ ~C ８ Alkyl, substituted, or unsubstituted C ６ ~C ４０ Aryl, substituted, or unsubstituted C ３ ~C ４０ Heteroaryl, SF ５ Selected from, Here, R １ , R ２ , R ３ , R ４ , and, R ５ The one or more substituents above are independent, D, CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl, fully fluorinated C １ ~C ８ Alkyl, or SF ５ Selected from, A compound of formula (I) according to any one of claims 1 to 10.

12. R １ , R ２ , R ３ , R ４ , and, R ５ Independently, H, D, CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl or fully fluorinated C １ ~C ８ Alkyl, substituted, or unsubstituted C ６ ~C ４０ Aryl, substituted, or unsubstituted C ３ ~C ４０ Heteroaryl, SF ５ Selected from, Here, R １ , R ２ , R ３ , R ４ , and, R ５ The one or more substituents above are independent, D, CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl, fully fluorinated C １ ~C ８ Alkyl, or SF ５ Selected from; and, R ａ , R ｂ , R ｃ ~R ｄ Independently, H, D, CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl or fully fluorinated C １ ~C ８ Alkyl, partially fluorinated C １ ~C ８ Alkoxy or fully fluorinated C １ ~C ８ Alkoxy, SF ５ Selected from; Here, R ａ , R ｂ , R ｃ , and, R ｄ At least one, at least two, or at least three of the following: CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl or fully fluorinated C １ ~C ８ Alkyl, partially fluorinated C １ ~C ８ Alkoxy or fully fluorinated C １ ~C ８ Alkoxy, SF ５ Selected from, A compound of formula (I) according to any one of claims 1 to 11.

13. R ａ , R ｂ , R ｃ ~R ｄ Independently, H, D, CN, CF ３ , partially fluorinated C １ ~C ８ Alkyl or fully fluorinated C １ ~C ８ Alkyl, partially fluorinated C １ ~C ８ Alkoxy or fully fluorinated C １ ~C ８ Alkoxy, SF ５ Selected from, not selected from halogen, A compound of formula (I) according to any one of claims 1 to 12.

14. X １ , X ２ , X ３ , X ４ , and, X ５ At least one, at least two, or at least three of these are independently, CF, CCl, CSF ５ CCN, CCF ３ CC ｍ F ２ｍ＋１ (m is 1 to 8), or CC ｍ F （２ｍ＋１）－ｔ H ｔ (where m = 1 to 8 and t = 1 to 2m) is selected; and / or, X １ , X ２ , X ３ , X ４ , and, X ５ At least one of is selected from N; and / or, X １ ~X ５ At least one of them is N, and X １ ~X ５ At least one or at least two of them independently, CF, CCl, CSF ５ CCN, CCF ３ CC ｍ F ２ｍ＋１ (m is 1 to 8), CC ｍ F （２ｍ＋１）－ｔ H ｔ (m is selected from 1 to 8 and t is 1 to 2m) A compound of formula (I) according to any one of claims 1 to 13.

15. X １ , X ２ , X ３ , X ４ , and, X ５ At least one, at least two, or at least three of these are independently, CSF ５ CCN, CCF ３ CC ｍ F ２ｍ＋１ (m is 1 to 8), or CC ｍ F （２ｍ＋１）－ｔ H ｔ (where m = 1 to 8 and t = 1 to 2m) is selected; or, X １ , X ２ , X ３ , X ４ , and, X ５ At least one of is selected from N; or, X １ ~X ５ At least one of them is N, and X １ ~X ５ At least one or at least two of them independently, CSF ５ CCN, CCF ３ CC ｍ F ２ｍ＋１ (m is 1 to 8), CC ｍ F （２ｍ＋１）－ｔ H ｔ (m is selected from 1 to 8 and t is 1 to 2m) A compound of formula (I) according to any one of claims 1 to 14.

16. X １ , X ２ , X ３ , X ４ , and, X ５ CR ｎ (n is selected from 1 to 5) X １ , X ２ , X ３ , X ４ , and, X ５ At least two or at least three of them independently, CCN, CCF ３ CC ｍ F ２ｍ＋１ (m is 1 to 8), or CC ｍ F （２ｍ＋１）－ｔ H ｔ (m = 1 to 8 and t = 1 to 2m) or, X １ , X ２ , X ３ , X ４ , and, X ５ The first three are selected from N, X １ , X ２ , X ３ , X ４ , and, X ５ At least one or at least two of them independently, CCN, CCF ３ CC ｍ F ２ｍ＋１ (m is 1 to 8), or CC ｍ F （２ｍ＋１）－ｔ H ｔ (m is selected from 1 to 8 and t is 1 to 2m) A compound of formula (I) according to any one of claims 1 to 15.

17. X １ ~X ５ At least one of them is independently selected from CH, CD, or N. Preferably, X １ ~X ５ At least one of them is independently selected from CH or CD. A compound of formula (I) according to any one of claims 1 to 16.

18. The compound of formula (I) above, sp ２ It does not contain F or Cl directly bonded to the hybrid carbon atoms. A compound of formula (I) according to any one of claims 1 to 17.

19. In equation (I), X １ , X ２ , X ３ , X ４ , and, X ５ Of these, ≥0 and ≤3, preferably ≥1 and ≤2, are selected from N. A compound of formula (I) according to any one of claims 1 to 18.

20. B in equation (II) １ T1-T64: 【Chemistry 9】 【change】 Selected from, A compound of formula (I) according to any one of claims 1 to 19.

21. The compounds of formula (I) are D1 to D365: Table 1 Selected from, A compound of formula (I) according to any one of claims 1 to 20.

22. The compounds of formula (I) are K1 to K365: 【Chemistry 10】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 Selected from, A compound of formula (I) according to any one of claims 1 to 21.

23. The compound of formula (I) is the compound of formula (I) according to any one of claims 1 to 22, having a LUMO energy level of ≤ -4.90 eV, preferably ≤ -4.95 eV.

24. An organic semiconductor layer comprising a compound according to any one of claims 1 to 23.

25. An organic semiconductor layer comprising a compound according to any one of claims 1 to 23, wherein the organic semiconductor layer is a hole injection layer and / or a p-type charge generation layer.

26. An organic electronic device comprising an anode layer, a cathode layer, and at least one organic semiconductor layer, wherein the at least one organic semiconductor layer is disposed between the anode layer and the cathode layer, and the at least one organic semiconductor layer is the hole injection layer and / or p-type charge generation layer according to claim 25.

27. The anode layer includes at least a first anode sublayer and a second anode sublayer. The organic electronic device according to claim 26.

28. The organic electronic device further comprises at least one photoactive layer, wherein the at least one photoactive layer is located between the anode layer and the cathode layer; preferably, at least one of the at least one organic semiconductor layers is located between the anode layer and the at least one photoactive layer. The organic electronic device according to claim 26 or 27.

29. The organic electronic device according to claim 28, wherein the photoactive layer is a light-emitting layer.

30. The organic electronic device according to any one of claims 26 to 29, wherein the organic electronic device is an electroluminescent device, an organic light-emitting diode (OLED), a light-emitting device, a thin-film transistor, a battery, a display device, or an organic solar cell (OPV).

31. A display device comprising an organic electronic device as described in any one of claims 26 to 30.

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