Composition for optoelectronic devices, and optoelectronic devices, image sensors, and electronic devices comprising the same

Abstract

Compositions for use in optoelectronic devices are provided, as well as optoelectronic devices, image sensors, and electronic devices including the same, said compositions for use in optoelectronic devices comprising n-type semiconductor compounds and p-type semiconductor compounds represented by Chemical Formula 1, wherein the groups in Chemical Formula 1 are the same as defined in the detailed specification. [Chemical Formula 1]

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2021-0000470, filed on January 4, 2021, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Examples of embodiments relate to compositions for optoelectronic devices, as well as optoelectronic devices, image sensors, and electronic devices including the same. Background Technology

[0004] Optoelectronic devices can convert light into electrical signals using the photoelectric effect. Optoelectronic devices can include photodiodes, phototransistors, etc., and can be applied to image sensors, etc.

[0005] Image sensors that incorporate photodiodes often require high resolution and therefore small pixels. Currently, silicon photodiodes are widely used. However, in some cases, silicon photodiodes exhibit degraded sensitivity due to the relatively small absorption area resulting from the relatively small pixel size. Therefore, organic materials that can replace silicon have been investigated. Summary of the Invention

[0006] Examples of embodiments provide compositions for optoelectronic devices that selectively absorb light in the green wavelength region and have improved thermal stability. Such compositions may be organic materials for optoelectronic devices, or may be included in organic materials for optoelectronic devices that have a relatively high extinction coefficient and selectively absorb light in specific wavelength regions depending on their molecular structure, and thus can simultaneously replace photodiodes and color filters, resulting in improved sensitivity and contributing to relatively high integration.

[0007] Some implementation examples also provide optoelectronic devices that can selectively absorb light in the green wavelength region and maintain improved efficiency in processes under high-temperature conditions.

[0008] Some exemplary implementations also provide an image sensor that includes the aforementioned optoelectronic device.

[0009] Some exemplary implementations also provide electronic devices that include the image sensor.

[0010] According to some exemplary embodiments, the composition for use in optoelectronic devices includes an n-type semiconductor compound and a p-type semiconductor compound represented by chemical formula 1.

[0011] [Chemical Formula 1]

[0012]

[0013] In chemical formula 1,

[0014] Ar 1 and Ar 2 Each can be an independently substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, or a fused ring thereof.

[0015] X 1 It can be -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g - or -CR ff R gg -, where R a1 R a2 R b R c R d R e R f and R g Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb and R cc R dd and R ee and R ff and R gg Each pair can be connected to each other to provide a ring structure.

[0016] X 2 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd Ree -、-(CR f R g ) n1 -、-(CR ff R gg )-、-(C(R m )=C(R n ))-、-(C(R mm )=C(R nn ))-、or-(C(R) p )=N)-, where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb and R cc R dd and R ee R ff and R gg and R mm and R nn Each pair can be connected to each other to provide a ring structure, and -(CR f R g ) n1 - n1 can be 1 or 2.

[0017] R 11 and R 12 Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy, wherein R 11 and R 12 They can exist independently or be connected to each other to provide a ring structure, or -CR 11 R 12 - Can be used with Ar 1 Or Ar 2 Connections are made to provide a ring structure.

[0018] Ar 3It may be a substituted or unsubstituted C6-C30 hydrocarbon ring group having at least one functional group selected from C=O, C=S, C=Se, and C=Te; a substituted or unsubstituted C2-C30 heterocyclic group having at least one functional group selected from C=O, C=S, C=Se, and C=Te; or a fused ring thereof; and

[0019] R 1 and R 2 Each of these can independently be hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C2-C30 acyl, halogen, cyano (-CN), cyano-containing groups, nitro, pentafluorothioalkyl (-SF5), hydroxyl, amino, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphate or its salt, -SiR a R b R c or combinations thereof, where R a R b and R c Each can be independently hydrogen or a substituted or unsubstituted C1-C10 alkyl group.

[0020] In some exemplary embodiments, a compound of chemical formula 1 may be represented by chemical formula 2A.

[0021] [Chemical Formula 2A]

[0022]

[0023] In chemical formula 2A,

[0024] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0025] Y 1 -Y 3 and Y 5 -Y 7 Each can be N or CR independently. k And Y 4 CR k , where R k It is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k (That is, defined as CR) kY 1 Y 2 Y 3 Y 4 Y 5 Y 6 , and / or Y 7 adjacent R in k (hereinafter the same) are connected to each other to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings.

[0026] In some example implementations, in chemical formula 2A, Y 4 CR k , where R k It is a halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl, or

[0027] Y 7 Can be N or CR k , where R k It can be halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl, and X 2 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1 -、-(C(R m )=C(R n ))-、or-(C(R) p )=N)-, where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each can be independently halogenated, C1-C20 haloalkyl, or C1-C20 cyanoalkyl, and -(CR f R g ) n1 - n1 can be 1 or 2.

[0028] In some example implementations, in chemical formula 2A, when Y 1 and Y5 For CR k At that time, Y 1 and Y 5 At least one of carbon (C) (i.e., -CR) 11 R 12 The Cs in the diagram (hereinafter the same) can be connected to each other to provide fused loops. Where Y... 5 The structure in which Y is bonded to carbon (C) can be represented by the chemical formula 2A-1, where Y is bonded to carbon (C). 1 The structure in which carbon (C) is bonded to each other can be represented by the chemical formula 2A-2.

[0029] [Chemical Formula 2A-1]

[0030]

[0031] In chemical formula 2A-1,

[0032] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0033] Y 1 -Y 3 Y 6 and Y 7 Each can be N or CR independently. k And Y 4 CR k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k Connected to each other to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0034] Cy can be a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, a substituted or unsubstituted C5-C30 cycloalkene group, a substituted or unsubstituted C3-C30 heterocyclic alkene group, or a fused ring thereof.

[0035] [Chemical Formula 2A-2]

[0036]

[0037] In chemical formula 2A-2,

[0038] X 1 X 2 Ar 3 R1 and R 2 Same as in chemical formula 1,

[0039] Y 2 -Y 3 and Y 5 -Y 7 Each can be N or CR independently. k And Y 4 CR k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0040] Cy can be a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, a substituted or unsubstituted C5-C30 cycloalkene group, a substituted or unsubstituted C3-C30 heterocyclic alkene group, or a fused ring thereof.

[0041] In some exemplary embodiments, a compound of chemical formula 1 may be represented by chemical formula 2B.

[0042] [Chemical Formula 2B]

[0043]

[0044] In chemical formula 2B,

[0045] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1,

[0046] Y 1 -Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0047] X 3It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g - or -CR ff R gg -, where R a1 R a2 R b R c R d R e R f and R g Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb and R cc R dd and R ee and R ff and R gg Each pair can be connected to each other to provide a ring structure.

[0048] In some example implementations, in chemical formula 2B, Y 4 Can be N or CR k , where R k It can be halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl, or

[0049] Y 5 Can be N or CR k , where R k It can be halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl, and X 2 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CRf R g ) n1 -、-(C(R m )=C(R n ))-、or-(C(R) p )=N)-, where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each can be independently halogenated, C1-C20 haloalkyl, or C1-C20 cyanoalkyl, and -(CR f R g ) n1 - n1 can be 1 or 2.

[0050] In some example implementations, in chemical formula 2B, X 3 (-NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e - or -CR f R g -) and carbon (C) can be linked together to provide a fused ring. This structure can be represented by the chemical formula 2B-1.

[0051] [Chemical Formula 2B-1]

[0052]

[0053] In chemical formula 2B-1,

[0054] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0055] X 31 It can be N, B, or SiR b GeR d CR f , Si, Ge or C, where R b R d and R fEach of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy.

[0056] Y 1 -Y 5 Each can be N or CR independently. k , where R k It is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k Connected to each other to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0057] Cy can be a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, a substituted or unsubstituted C5-C30 cycloalkene group, a substituted or unsubstituted C3-C30 heterocyclic alkene group, or a fused ring thereof.

[0058] In some example implementations, in chemical formula 2B, when Y 1 For CR k At that time, Y 1 Carbon (C) atoms can be linked together to provide fused rings. This structure can be represented by the chemical formula 2B-2.

[0059] [Chemical Formula 2B-2]

[0060]

[0061] In chemical formula 2B-2,

[0062] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0063] X 3 and Y 5 Same as in chemical formula 2B,

[0064] Y 2 -Y 4 Each can be N or CR independently. k , where R k It is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R kConnected to each other to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0065] Cy can be a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, a substituted or unsubstituted C5-C30 cycloalkene group, a substituted or unsubstituted C3-C30 heterocyclic alkene group, or a fused ring thereof.

[0066] In some exemplary embodiments, compounds of chemical formula 1 may be represented by chemical formula 2C.

[0067] [Chemical formula 2C]

[0068]

[0069] In chemical formula 2C,

[0070] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0071] Y 1 -Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0072] X 3 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g - or -CR ff R gg -, where Ra1 R a2 R b R c R d R e R f and R g Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb and R cc R dd and R ee and R ff and R gg Each pair can be connected to each other to provide a ring structure.

[0073] In some example implementations, in chemical formula 2C, Y 4 Can be N or CR k , where R k It can be halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl, or

[0074] X 3 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e - or -CR f R g -, where R a1 R a2 R b R c R d R e R f and R g Each can be independently a halogen, a C1-C20 haloalkyl, or a C1-C20 cyanoalkyl, and X 2 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f Rg ) n1 -、-(C(R m )=C(R n ))-、or-(C(R) p )=N)-, where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each can be independently halogenated, C1-C20 haloalkyl, or C1-C20 cyanoalkyl, and -(CR f R g ) n1 - n1 can be 1 or 2.

[0075] In chemical formula 2C, when Y 5 For CR k At that time, Y 5 Carbon (C) atoms can be linked together to provide fused rings. This structure can be represented by the chemical formula 2C-1.

[0076] [Chemical formula 2C-1]

[0077]

[0078] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0079] X 3 Same as in chemical formula 2C,

[0080] Y 1 -Y 4 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0081] Cy can be a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, a substituted or unsubstituted C5-C30 cycloalkene group, a substituted or unsubstituted C3-C30 heterocyclic alkene group, or a fused ring thereof.

[0082] In some example implementations, in chemical formula 2C, when Y 1 For CR k At that time, Y 1 Carbon (C) atoms can be linked together to provide fused rings. This structure can be represented by the chemical formula 2C-2.

[0083] [Chemical formula 2C-2]

[0084]

[0085] In the chemical formula 2C-2,

[0086] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0087] X 3 and Y 5 Same as in chemical formula 2C,

[0088] Y 2 -Y 4 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0089] Cy can be a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, a substituted or unsubstituted C5-C30 cycloalkene group, a substituted or unsubstituted C3-C30 heterocyclic alkene group, or a fused ring thereof.

[0090] In some exemplary embodiments, compounds of chemical formula 1 may be represented by chemical formula 2D.

[0091] [Chemical Formula 2D]

[0092]

[0093] In chemical formula 2D,

[0094] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0095] Y 1 -Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0096] X 3 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g - or -CR ff R gg -, where R a1 R a2 R b R c R d R e R f and R g Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb and R cc R dd and R ee and R ff and R gg Each pair can be connected to each other to provide a ring structure.

[0097] In some example implementations, in chemical formula 2D, Y 4 Can be N or CR k , where R k It is a halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl, or

[0098] Y 3 Can be N or CR k , where R k It can be halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl, and X 2 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1 -、-(C(R m )=C(R n ))-、or-(C(R) p )=N)-, where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each can be independently halogenated, C1-C20 haloalkyl, or C1-C20 cyanoalkyl, and -(CR f R g ) n1 - n1 can be 1 or 2.

[0099] In chemical formula 2D, when Y 1 For CR k At that time, Y 1 Carbon (C) atoms can be linked together to provide fused rings. This structure can be represented by the chemical formula 2D-1.

[0100] [Chemical formula 2D-1]

[0101]

[0102] In chemical formula 2D-1,

[0103] X1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0104] X 3 Same as in chemical formula 2D,

[0105] Y 2 -Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0106] Cy can be a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, a substituted or unsubstituted C5-C30 cycloalkene group, a substituted or unsubstituted C3-C30 heterocyclic alkene group, or a fused ring thereof.

[0107] In chemical formula 2D, when X 3 For -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e - or -CR f R g - At that time, X 3 Carbon (C) atoms can be linked together to provide fused rings. This structure can be represented by the chemical formula 2D-2.

[0108] [Chemical formula 2D-2]

[0109]

[0110] In the chemical formula 2D-2,

[0111] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0112] X 31 It can be N, B, or SiR b GeR d CRf , Si, Ge or C, where R b R d and R f Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy.

[0113] Y 1 -Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0114] Cy can be a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, a substituted or unsubstituted C5-C30 cycloalkene group, a substituted or unsubstituted C3-C30 heterocyclic alkene group, or a fused ring thereof.

[0115] In some exemplary embodiments, compounds of chemical formula 1 may be represented by chemical formula 2E.

[0116] [Chemical formula 2E]

[0117]

[0118] In chemical formula 2E,

[0119] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0120] X 3 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeRdd R ee -、-CR f R g - or -CR ff R gg -, where R a1 R a2 R b R c R d R e R f and R g Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb and R cc R dd and R ee and R ff and R gg Each pair can be connected to each other to provide a ring structure, and

[0121] Y 1 -Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be connected to each other to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings.

[0122] In some example implementations, in chemical formula 2E, X 3 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e - or -CR f R g -, where R a1 R a2 R b R c R d R e R f and R gEach can be independently a halogen, a C1-C20 haloalkyl, or a C1-C20 cyanoalkyl, or

[0123] Y 3 Can be N or CR k , where R k It can be halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl, and X 2 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1 -、-(C(R m )=C(R n ))-、or-(C(R) p )=N)-, where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each can be independently halogenated, C1-C20 haloalkyl, or C1-C20 cyanoalkyl, and -(CR f R g ) n1 - n1 can be 1 or 2.

[0124] In some example implementations, in chemical formula 2E, when Y 1 and Y 4 For CR k At that time, Y 1 and Y 4 One of the atoms and carbon (C) can be linked together to provide a fused ring. This structure can be represented by chemical formula 2E-1 or chemical formula 2E-2.

[0125] [Chemical formula 2E-1]

[0126]

[0127] In chemical formula 2E-1,

[0128] X 1 X 2 Ar3 R 1 and R 2 Same as in chemical formula 1,

[0129] X 3 Same as in chemical formula 2E,

[0130] Y 2 -Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0131] Cy can be a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, a substituted or unsubstituted C5-C30 cycloalkene group, a substituted or unsubstituted C3-C30 heterocyclic alkene group, or a fused ring thereof.

[0132] [Chemical formula 2E-2]

[0133]

[0134] In chemical formula 2E-2,

[0135] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0136] X 3 Same as in chemical formula 2E,

[0137] Y 1 -Y 3 and Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0138] Cy can be a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, a substituted or unsubstituted C5-C30 cycloalkene group, a substituted or unsubstituted C3-C30 heterocyclic alkene group, or a fused ring thereof.

[0139] In some exemplary embodiments, in chemical formula 1, X 1 X 2 、 and -CR 11 R 12 In this context, the ring structure can be a helical ring structure or a fused ring structure.

[0140] In some implementations, the spiro-ring structure may include a portion represented by chemical formula 3.

[0141] [Chemical Formula 3]

[0142]

[0143] In chemical formula 3,

[0144] X a and X b They can be independently -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、or-GeR dd R ee -, where R a1 R a2 R b R c R d and R e Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb and R cc and R dd and R ee Each pair can be connected to each other to provide a ring structure.

[0145] L a Can be -O-, -S-, -Se-, -Te-, -NR a1 -、-BR a2-、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1 -、-(C(R p ) = N)-, or a single bond, where R a1 R a2 R b R c R d R e R f R g and R p Each can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy, and -(CR f R g ) n1 -n1 can be 1 or 2, and

[0146] The hydrogen atoms in each ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0147] In some exemplary embodiments, in chemical formula 3, one or more CHs present in the aromatic rings of portions (3), (4), (5), (6), (7), (8), or (9) may be replaced by N.

[0148] In some example implementations, in chemical formula 1, Ar 3 It can be a cyclic group represented by chemical formula 4.

[0149] [Chemical Formula 4]

[0150]

[0151] In chemical formula 4,

[0152] Ar 3 It can be a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group.

[0153] Z 1 It can be O, S, Se, or Te, and

[0154] Z 2 It can be O, S, Se, Te, or CRa R b , where R a and R b Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR a R b At that time, R a and R b At least one of them is a cyano group or a group containing a cyano group.

[0155] In some example implementations, in chemical formula 1, Ar 3 It can be a cyclic group represented by one of the chemical formulas 5A to 5G.

[0156] [Chemical Formula 5A]

[0157]

[0158] In chemical formula 5A,

[0159] Z 1 It can be O, S, Se, or Te.

[0160] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR a R b At that time, R a and R b At least one of them is a cyano group or a group containing a cyano group.

[0161] Z 3 Can be N or CR c , where R c It is hydrogen, deuterium, or a substituted or unsubstituted C1-C10 alkyl group.

[0162] R 11 R 12 R 13 R 14 and R 15 Each of these can independently be hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, halogen, cyano (-CN), a cyano-containing group, or a combination thereof, wherein R 12 and R 13 and R14 and R 15 They can exist independently or connect with each other to provide fused aromatic rings.

[0163] n can be 0 or 1, and

[0164] *Can be a connection point.

[0165] [Chemical Formula 5B]

[0166]

[0167] In chemical formula 5B,

[0168] Z 1 It can be O, S, Se, or Te.

[0169] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR a R b At that time, R a and R b At least one of them is a cyano group or a group containing a cyano group.

[0170] Z 3 It can be O, S, Se, Te, or C(R) a (CN), where R a It is hydrogen, cyano (-CN), or C1-C10 alkyl.

[0171] R 11 and R 12 Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, halogen, cyano (-CN), or a combination thereof, and

[0172] * Can be a connection point.

[0173] [Chemical formula 5C]

[0174]

[0175] In the chemical formula 5C,

[0176] Z 1 It can be O, S, Se, or Te.

[0177] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR a R b At that time, R a and R b At least one of them is a cyano group or a group containing a cyano group.

[0178] R 11 R 12 and R 13 Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, halogen, cyano (-CN), or a combination thereof, and

[0179] * Can be a connection point.

[0180] [Chemical Formula 5D]

[0181]

[0182] In chemical formula 5D,

[0183] Z 1 It can be O, S, Se, or Te.

[0184] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR a R b At that time, R a and R b At least one of them is a cyano group or a group containing a cyano group.

[0185] Z 3 Can be N or CR c , where R c It can be hydrogen or a substituted or unsubstituted C1-C10 alkyl group.

[0186] G 1 It can be O, S, Se, Te, SiR x R yor GeR z R w , where R x R y R z and R w Each can be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, or substituted or unsubstituted C6-C20 aryl.

[0187] R 11 R 12 and R 13 Each of these can independently be hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, halogen, cyano, a cyano-containing group, or a combination thereof, wherein R 12 and R 13 They can exist independently or connect with each other to provide fused aromatic rings.

[0188] n can be 0 or 1, and

[0189] * Can be a connection point.

[0190] [Chemical formula 5E]

[0191]

[0192] In chemical formula 5E,

[0193] Z 1 It can be O, S, Se, or Te.

[0194] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR a R b At that time, R a and R b At least one of them is a cyano group or a group containing a cyano group.

[0195] Z 3 Can be N or CR c , where R c It can be hydrogen or a substituted or unsubstituted C1-C10 alkyl group.

[0196] G 2 It can be O, S, Se, Te, SiR xR y or GeR z R w , where R x R y R z and R w Each can be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, or substituted or unsubstituted C6-C20 aryl.

[0197] R 11 R 12 and R 13 Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, halogen, cyano, cyano-containing groups, or combinations thereof.

[0198] n can be 0 or 1, and

[0199] * Can be a connection point.

[0200] [Chemical formula 5F]

[0201]

[0202] In the chemical formula 5F,

[0203] Z 1 It can be O, S, Se, or Te.

[0204] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR a R b At that time, R a and R b At least one of them is a cyano group or a group containing a cyano group.

[0205] R 11 It can be hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, halogen, cyano (-CN), a cyano-containing group, or a combination thereof, and

[0206] G 3 It can be O, S, Se, Te, SiR x R yor GeR z R w , where R x R y R z and R w Each can be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, or substituted or unsubstituted C6-C20 aryl.

[0207] [Chemical Formula 5G]

[0208]

[0209] In chemical formula 5G,

[0210] Z 1 It can be O, S, Se, or Te.

[0211] R a and R b Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a group containing a cyano group, and

[0212] Z 2 -Z 4 Each can be independently O, S, Se, Te, or CR c R d , where R c and R d Each is independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR c R d At that time, R c and R d At least one of them is a cyano group or a group containing a cyano group.

[0213] In some exemplary embodiments, the composition for optoelectronic devices may have a maximum absorption wavelength (λ) in the thin-film state within a wavelength range greater than or equal to about 500 nm and less than or equal to about 600 nm. 最大 ).

[0214] In some exemplary embodiments, the composition for optoelectronic devices can exhibit a light absorption curve with a half-width (FWHM) of about 50 nm to about 110 nm in the thin film state.

[0215] According to some exemplary embodiments, an optoelectronic device (e.g., an organic optoelectronic device) includes: a first electrode and a second electrode facing each other, and an active layer between the first electrode and the second electrode and including the composition for the optoelectronic device, the composition for the optoelectronic device including an n-type semiconductor compound and a p-type semiconductor compound represented by chemical formula 1.

[0216] According to some exemplary embodiments, an image sensor including the aforementioned optoelectronic device is provided.

[0217] In some implementation examples, the image sensor may include a semiconductor substrate integrating a plurality of first photosensitive devices configured to sense light in the blue wavelength region and a plurality of second photosensitive devices configured to sense light in the red wavelength region, and the photoelectric device may be on the semiconductor substrate and configured to selectively sense light in the green wavelength region.

[0218] In some implementations, the image sensor may further include a color filter layer comprising a blue filter configured to selectively transmit light in the blue wavelength region and a red filter configured to selectively transmit light in the red wavelength region.

[0219] In some implementations, the first and second photosensing devices may be stacked vertically on the semiconductor substrate.

[0220] In some exemplary embodiments, the image sensor may include: a green optoelectronic device configured to selectively sense light in a green wavelength region and being the optoelectronic device; a blue optoelectronic device configured to selectively sense light in a blue wavelength region; and a red optoelectronic device configured to selectively sense light in a red wavelength region, wherein the green optoelectronic device, the blue optoelectronic device, and the red optoelectronic device may be stacked.

[0221] According to some exemplary embodiments, an electronic device including the image sensor is provided.

[0222] The composition for optoelectronic devices is capable of selectively absorbing light in the green wavelength region and exhibits excellent thermal stability and charge mobility. The wavelength selectivity of the composition in the green wavelength region can be increased to improve the efficiency of the device, and optoelectronic devices, image sensors, and electronic devices whose performance does not degrade even during high-temperature processes are provided. Attached Figure Description

[0223] Figure 1 To show a cross-sectional view of an optoelectronic device according to some exemplary embodiments,

[0224] Figure 2To show a cross-sectional view of an optoelectronic device according to some exemplary embodiments,

[0225] Figure 3 To illustrate a schematic top view of an organic CMOS image sensor according to some exemplary embodiments,

[0226] Figure 4 for Figure 3 A cross-sectional view of an organic CMOS image sensor.

[0227] Figure 5 This is a schematic cross-sectional view of an organic CMOS image sensor according to some exemplary embodiments.

[0228] Figure 6 This is a schematic cross-sectional view of an organic CMOS image sensor according to some exemplary embodiments.

[0229] Figure 7 This is a cross-sectional view of an organic CMOS image sensor according to some exemplary embodiments.

[0230] Figure 8 To illustrate a schematic diagram of an organic CMOS image sensor according to some exemplary embodiments,

[0231] Figure 9 A block diagram of a digital camera including an image sensor according to some example embodiments, and

[0232] Figure 10 This is a schematic diagram illustrating an electronic device according to some example implementations. Detailed Implementation

[0233] The following describes in detail some exemplary implementations so that those skilled in the art can readily implement them. However, practical applications can be implemented in many different forms and are not limited to the exemplary implementations described herein.

[0234] In the accompanying drawings, the thicknesses of layers, films, panels, regions, etc., are enlarged for clarity. Throughout the specification, the same reference numerals denote the same elements. It will be understood that when an element, such as a layer, film, region, or substrate, is referred to as being "on" another element, it may be directly on said other element or there may be intermediate elements present. Conversely, when an element is referred to as being "directly on" another element, there are no intermediate elements.

[0235] In the accompanying drawings, for clarity of some exemplary embodiments, parts unrelated to the description have been omitted, and in the specification, the same or similar constituent elements are always represented by the same reference numerals.

[0236] As used herein, “at least one of A, B, or C”, “one of A, B, C, or combinations thereof” and “one of A, B, C, or combinations thereof” refer to the constituent elements and their combinations (e.g., A; B; C; A and B; A and C; B and C; or A, B, and C).

[0237] As used herein, unless otherwise specifically defined, “substituted” means that the hydrogen atom of a compound or functional group is replaced by: a halogen atom (F, Br, Cl, or I), a hydroxyl group, a nitro group, a cyano group, an azide group, an amido group, an amino group (-NR'R, where R' and R” are each independently a hydrogen atom, a C1-C20 alkyl group, or a C6-C30 aryl group), a hydrazine group, a hydrazone group, a carbonyl group, a carbamoyl group, a thiol group, or an ester group. The group consisting of an alkyl group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C30 aryl group, a C7-C30 aralkyl group, a C2-C20 heteroaryl group, a C3-C20 heteroaryl group, a C3-C30 cycloalkyl group, a C3-C15 cycloalkenyl group, a C6-C15 cycloalkynyl group, a C2-C20 heterocycloalkyl group, and combinations thereof.

[0238] "Aromatic group" refers to a hydrocarbon ring group that has an aromatic ring, including monocyclic and polycyclic hydrocarbon ring groups, and the other ring of the polycyclic hydrocarbon ring group can be an aromatic ring or a non-aromatic ring. Aromatic groups can be C6-C30 aromatic groups, C6-C20 aromatic groups, or C6-C10 aromatic groups.

[0239] "Heteroaromatic groups" refer to aromatic groups that include 1-3 heteroatoms selected from N, O, S, P, and Si in the ring. Heteroaromatic groups can be C3-C30 heteroaromatic groups, C3-C20 heteroaromatic groups, or C3-C10 heteroaromatic groups.

[0240] As used herein, "hydrocyclic group" may be a C3-C30 hydrocarbon cyclic group. The hydrocarbon cyclic group may be an aromatic hydrocarbon cyclic group (e.g., a C6-C30 aromatic group, a C6-C20 aromatic group, or a C6-C10 aromatic group, or a C6-C30 aryl, C6-C20 aryl, or C6-C10 aryl), an alicyclic hydrocarbon cyclic group (e.g., a C3-C30 cycloalkyl, a C5-C30 cycloalkyl, a C3-C20 cycloalkyl, or a C3-C10 cycloalkyl), or a fused cyclic group thereof. For example, a fused ring group can refer to a fused ring of an aromatic ring (aromatic ring) and a non-aromatic ring (alicyclic ring), such as a fused ring in which at least one aromatic ring (aromatic ring) such as a C6-C30 aromatic group, C6-C20 aromatic group, or C6-C10 aromatic group or a C6-C30 aryl, C6-C20 aryl, or C6-C10 aryl and at least one non-aromatic ring (alicyclic ring) such as a C3-C30 cycloalkyl, C3-C20 cycloalkyl, or C3-C10 cycloalkyl is fused with each other.

[0241] As used herein, a "heterocyclic group" may be a C2-C30 heterocyclic group. A heterocyclic group may be a cyclic group in which at least one, for example, 1-3 carbons of an aromatic cyclic group (e.g., a C6-C30 aromatic group, a C6-C20 aromatic group, or a C6-C10 aromatic group, or a C6-C30 aryl, C6-C20 aryl, or C6-C10 aryl), an alicyclic cyclic group (e.g., a C3-C30 cycloalkyl, a C3-C20 cycloalkyl, or a C3-C10 cycloalkyl), and its fused cyclic group are replaced by heteroatoms selected from N, O, S, P, and Si. Additionally, at least one carbon atom of the heterocyclic group may be replaced by a thiocarbonyl group (C=S).

[0242] As used herein, unless otherwise specifically defined, “hybrid” refers to a mixture of 1-3 heteroatoms selected from N, O, S, P, and Si.

[0243] As used in this article, "alkyl" refers to a monovalent straight-chain or branched saturated hydrocarbon group such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, etc.

[0244] As used herein, “cycloalkyl” refers to a saturated hydrocarbon cyclic group in which the ring atom is a single carbon atom, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

[0245] As used herein, “aryl” refers to a cyclic functional group in which all elements of the ring have conjugated p orbitals, and can be monocyclic, polycyclic, or fused polycyclic (e.g., a ring sharing adjacent carbon pairs) functional groups.

[0246] As used herein, unless otherwise defined, "a cyano-containing group" refers to a monovalent group in which at least one hydrogen atom is replaced by a cyano group, such as a C1-C30 alkyl, C2-C30 alkenyl, or C2-C30 alkynyl group. A cyano-containing group also refers to a divalent group, such as =CR x' -(CR x R y ) p -CR y' (CN)2, where R x R y R x' and R y' Each group may be independently hydrogen or a C1-C10 alkyl group, and p is an integer from 0 to 10 (or 1 to 10). Specific examples of cyano groups include dicyanomethyl, dicyanovinyl, cyanoethynyl, etc. As used herein, cyano groups do not include functional groups containing only a cyano (-CN) group.

[0247] As used herein, unless otherwise defined, "aromatic hydrocarbon group" may include, but is not limited to, C6-C30 aromatic hydrocarbon groups such as phenyl and naphthyl, C6-C30 aryl, and C6-C30 arylene groups.

[0248] As used herein, unless otherwise defined, “aliphatic hydrocarbon group” may include, but is not limited to, C1-C15 alkyl groups such as methyl, ethyl, propyl, etc., C1-C15 alkylene groups, C2-C15 alkenyl groups such as vinyl or propenyl, and C2-C15 ynyl groups such as ethynyl or propynyl.

[0249] As used herein, unless otherwise defined, "aromatic ring" refers to a C6-C10 hydrocarbon ring group (e.g., C6-C10 aryl) that provides a conjugated structure or a C2-C10 heterocyclic group (e.g., C2-C10 heteroaryl) that provides a conjugated structure.

[0250] As used herein, unless otherwise defined, "spirocyclic structure" can be a substituted or unsubstituted C5-C30 cyclic group, a substituted or unsubstituted C2-C30 heterocyclic group, or a fused ring thereof. A substituted or unsubstituted C5-C30 cyclic group can be, for example, a substituted or unsubstituted C5-C30 cycloalkyl group (e.g., a substituted or unsubstituted C5-C20 cycloalkyl group or a substituted or unsubstituted C5-C10 cycloalkyl group) or a substituted or unsubstituted C6-C30 aryl group (e.g., a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C6-C10 aryl group), and a substituted or unsubstituted C2-C30 heterocyclic group can be, for example, a substituted or unsubstituted C2-C20 heterocyclic alkyl group (e.g., a substituted or unsubstituted C2-C10 heterocyclic alkyl group) or a substituted or unsubstituted C2-C20 heteroaryl group (e.g., a substituted or unsubstituted C2-C10 heteroaryl group).

[0251] As used herein, unless otherwise defined, a “fused ring” is a fused ring of two or more substituted or unsubstituted C5-C30 hydrocarbon ring groups, a fused ring of two or more substituted or unsubstituted C2-C30 heterocyclic groups, or a fused ring of a substituted or unsubstituted C5-C30 hydrocarbon ring group and a substituted or unsubstituted C2-C30 heterocyclic group (e.g., fluorene). Here, hydrocarbon ring groups and heterocyclic groups are as defined above.

[0252] As used herein, unless otherwise defined, “combination” means a mixture of two or more, substitution in which one substituent is replaced by another, fused together, or linked together by a single bond or C1-C10 alkylene bond.

[0253] When the term “about” is used in this specification with respect to numerical values, it is intended that the relevant numerical value includes manufacturing or operational tolerances (e.g., ±10%) near the stated value.

[0254] The following describes compositions for optoelectronic devices according to some exemplary embodiments. These compositions for optoelectronic devices include n-type semiconductor compounds and p-type semiconductor compounds represented by Chemical Formula 1.

[0255] [Chemical Formula 1]

[0256]

[0257] In chemical formula 1,

[0258] Ar 1 and Ar 2 Each can be an independently substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, or a fused ring thereof.

[0259] X1 It can be -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g - or -CR ff R gg -, where R a1 R a2 R b R c R d R e R f and R g Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R ee R ff and R gg Each can be independent of the other, where w is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6) (CH2). w Or heteroatoms O, NR w (where R) w (is hydrogen or C1-C10 alkyl), S, Se or Te, and / or R bb and R cc R dd and R ee and R ff and R gg Each pair connects to each other to provide a ring structure.

[0260] X 2 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc-、-GeR d R e -、-GeR dd R ee -、-(CR f R g ) n1 -、-(CR ff R gg )-、-(C(R m )=C(R n ))-、-(C(R mm )=C(R nn ))-、or-(C(R) p )=N)-, where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R ee R ff R gg R mm and R nn Each can be independently defined as (CH2) where v is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6). v Or heteroatoms O, NR v (where R) v (is hydrogen or C1-C10 alkyl), S, Se or Te, and / or R bb and R cc R dd and R ee R ff and R gg and R mm and R nn Each pair can be connected to each other to provide a ring structure, and -(CR f R g ) n1 - n1 can be 1 or 2.

[0261] R11 and R 12 Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy, wherein R 11 and R 12 They can exist independently or be connected to each other to provide a ring structure, or -CR 11 R 12 - Can be used with Ar 1 Or Ar 2 Connections are made to provide a ring structure.

[0262] Ar 3 It may be a substituted or unsubstituted C6-C30 hydrocarbon ring group having at least one functional group selected from C=O, C=S, C=Se, and C=Te; a substituted or unsubstituted C2-C30 heterocyclic group having at least one functional group selected from C=O, C=S, C=Se, and C=Te; or a fused ring thereof; and

[0263] R 1 and R 2 Each of these can independently be hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C2-C30 acyl, halogen, cyano (-CN), cyano-containing groups, nitro, pentafluorothioalkyl (-SF5), hydroxyl, amino, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphate or its salt, -SiR a R b R c or combinations thereof, where R a R b and R c Each can be independently hydrogen or a substituted or unsubstituted C1-C10 alkyl group.

[0264] Compounds represented by chemical formula 1 include: an electron donor moiety comprising a first ring moiety including nitrogen (N) and carbon (C) and containing X. 1 The second ring part; and by Ar 3 The electron acceptor portion is represented; it includes the first ring portion of nitrogen (N) and carbon (C) and contains X. 1 The second ring portion consists of nitrogen (N) and X. 2 The third ring portions fuse together to provide a fused ring. In Formula 1, this is achieved by using nitrogen (N) and X... 2 The third ring portion makes the first ring portion, which includes nitrogen (N) and carbon (C), and contains X. 1The second ring portion is fused to provide a fused ring, which improves the stability of the compound's molecular structure and limits and / or prevents the decomposition of the compound during deposition, thereby improving device reliability. Additionally, in the first ring portion comprising nitrogen (N) and carbon (C), Ar... 1 and Ar 2 The stability of the molecular structure can be further improved by connecting carbon (C).

[0265] Compounds represented by chemical formula 1 include: an electron donor moiety comprising a first ring moiety including nitrogen (N) and carbon (C) and containing X. 1 The second ring section; and the part by Ar 3 The electron acceptor portion is represented; it includes the first ring portion of nitrogen (N) and carbon (C) and contains X. 1 The second ring portion consists of nitrogen (N) and X. 2 The third ring portion fused together to provide a fused ring.

[0266] In some exemplary embodiments, a compound of chemical formula 1 may be represented by chemical formula 2A.

[0267] [Chemical Formula 2A]

[0268]

[0269] In chemical formula 2A,

[0270] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0271] Y 1 -Y 3 and Y 5 -Y 7 Each can be N or CR independently. k And Y 4 CR k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be connected to each other to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings.

[0272] In some example implementations, in chemical formula 2A, Y 4 CRk , where R k It is a halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl. In this case, Y 4 N, X 1 And Ar 3 The functional groups (C=O, C=S, C=Se, or C=Te) enhance intramolecular interactions, thereby increasing the absorption intensity at a specific wavelength.

[0273] In some example implementations, in chemical formula 2A, Y 7 Can be N or CR k , where R k It is a halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl, and X 2 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1 -、-(C(R m )=C(R n ))-、or-(C(R) p )=N)-, where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each can be independently halogenated, C1-C20 haloalkyl, or C1-C20 cyanoalkyl, and -(CR f R g ) n1 - n1 can be 1 or 2. In this case, Y 7 and X 2 It can enhance intramolecular interactions, thereby improving the absorption intensity at specific wavelengths.

[0274] In some example implementations, in chemical formula 2A, when Y 1 and Y 5 For CR k At that time, Y 1 and Y 5At least one carbon (C) can be connected to each other to provide a fused ring. The structure can be represented by chemical formula 2A-1 or chemical formula 2A-2.

[0275] [Chemical Formula 2A-1]

[0276]

[0277] In chemical formula 2A-1,

[0278] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0279] Y 1 -Y 3 Y 6 and Y 7 Each can be N or CR independently. k And Y 4 CR k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0280] Cy can be a substituted or unsubstituted C6-C30 aromatic group, such as a substituted or unsubstituted C6-C20 aromatic group, or a substituted or unsubstituted C6-C10 aromatic group; a substituted or unsubstituted C3-C30 heteroaromatic group, such as a substituted or unsubstituted C3-C20 heteroaromatic group, or a substituted or unsubstituted C3-C10 heteroaromatic group; a substituted or unsubstituted C5-C30 cycloalkenyl group, such as a substituted or unsubstituted C5-C20 cycloalkenyl group, or a substituted or unsubstituted C5-C10 cycloalkenyl group; a substituted or unsubstituted C3-C30 heterocyclic alkene group, such as a substituted or unsubstituted C5-C30 heterocyclic alkene group, a substituted or unsubstituted C5-C20 heterocyclic alkene group, or a substituted or unsubstituted C5-C10 heterocyclic alkene group; or a fused ring thereof.

[0281] [Chemical Formula 2A-2]

[0282]

[0283] In chemical formula 2A-2,

[0284] X 1 X2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0285] Y 2 -Y 3 and Y 5 -Y 7 Each can be N or CR independently. k And Y 4 CR k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0286] Cy can be a substituted or unsubstituted C6-C30 aromatic group, such as a substituted or unsubstituted C6-C20 aromatic group, or a substituted or unsubstituted C6-C10 aromatic group; a substituted or unsubstituted C3-C30 heteroaromatic group, such as a substituted or unsubstituted C3-C20 heteroaromatic group, or a substituted or unsubstituted C3-C10 heteroaromatic group; a substituted or unsubstituted C5-C30 cycloalkenyl group, such as a substituted or unsubstituted C5-C20 cycloalkenyl group, or a substituted or unsubstituted C5-C10 cycloalkenyl group; a substituted or unsubstituted C3-C30 heterocyclic alkene group, such as a substituted or unsubstituted C5-C30 heterocyclic alkene group, a substituted or unsubstituted C5-C20 heterocyclic alkene group, or a substituted or unsubstituted C5-C10 heterocyclic alkene group; or a fused ring thereof.

[0287] In some exemplary embodiments, the Cy group in Formula 2A-1 and Formula 2A-2 may be an aromatic group, a heteroaromatic group, a cycloalkenyl group, or a heterocyclic alkene group, and they may have a 5- to 10-membered ring structure. The heteroaromatic group or heterocyclic alkene group may include N in the ring.

[0288] When Cy of chemical formula 2A-1 has a 6-membered ring structure, the compound of chemical formula 2A-1 can be represented by chemical formula 2A-11a.

[0289] [Chemical Formula 2A-11a]

[0290]

[0291] In chemical formula 2A-11a,

[0292] X 1 X 2Ar 3 R 1 and R 2 Same as in chemical formula 1, and

[0293] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0294] In some exemplary embodiments, the CH of the 6-membered ring structure (e.g., the benzene ring and / or the cyclohexadiene ring) in formula 2A-11a (besides being Y) 4 (In addition to CH) can be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0295] When Cy of chemical formula 2A-2 has a 6-membered ring structure, the compound of chemical formula 2A-2 can be represented by chemical formula 2A-21a.

[0296] [Chemical Formula 2A-21a]

[0297]

[0298] In chemical formula 2A-21a,

[0299] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1, and

[0300] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0301] In some exemplary embodiments, the CH of the 6-membered ring structure (e.g., the benzene ring and / or the cyclohexadiene ring) in formula 2A-21a (besides being Y) 4 (In addition to CH) can be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0302] In some example implementations, in chemical formula 2A, Y 1 (CR k Y and carbon (C) can be linked together to provide a first fused ring, and Y 5 (CR kThe first fused ring and carbon (C) can be linked together to provide a second fused ring. When both the first and second fused rings have a 6-membered ring structure, they can be represented by chemical formulas 2A-3a.

[0303] [Chemical formula 2A-3a]

[0304]

[0305] In chemical formula 2A-3a,

[0306] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1, and

[0307] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0308] In some exemplary embodiments, the CH of the 6-membered ring structure (e.g., the benzene ring and / or the cyclohexadiene ring) in formulas 2A-3a (besides being Y) 4 (In addition to CH) can be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0309] In some example implementations, in chemical formula 2A, when Y 1 -Y 4 For CR k And adjacent R k When connected to each other to provide fused rings (substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, substituted or unsubstituted C5-C30 cycloalkenes, substituted or unsubstituted C3-C30 heterocyclic alkenes, or combinations thereof), they may be represented by one of chemical formulas 2A-41 to 2A-44.

[0310]

[0311] In chemical formulas 2A-41 to 2A-44

[0312] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1,

[0313] X 4 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g -、-CR ff R gg -、-CR h =CR i - or -CR hh =CR ii -, where R a1 R a2 R b R c R d R e R f R g R h and R i Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R ee R ff R gg R hh and R ii Each can be independently defined as (CH2) where t is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6). t Or heteroatoms O, NR t (where R) t (is hydrogen or C1-C10 alkyl), S, Se or Te, and / or R bb and R cc R dd and R ee R ff and R gg and R hh and R iiEach pair can be connected to each other to provide a ring structure.

[0314] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0315] In some exemplary embodiments, in chemical formulas 2A-41 to 2A-44, the CH of the aromatic ring (except as Y) 4 (In addition to CH) can be replaced by N, and one or more (e.g., 1, 2 or 3) N may be included in an aromatic ring.

[0316] In chemical formula 2A, when Y 5 -Y 7 For CR k And adjacent R k When connected to each other to provide fused rings (substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, substituted or unsubstituted C5-C30 cycloalkenyl groups, substituted or unsubstituted C3-C30 heterocyclic alkenyl groups, or combinations thereof), they may be represented by one of chemical formulas 2A-45 to 2A-48.

[0317]

[0318] In chemical formulas 2A-45 to 2A-48

[0319] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1,

[0320] X 4 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g -、-CR ff Rgg -、-CR h =CR i - or -CR hh =CR ii -, where R a1 R a2 R b R c R d R e R f R g R h and R i Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R ee R ff R gg R hh and R ii Each can be independently defined as (CH2) where t is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6). t Or heteroatoms O, NR t (where R) t (is hydrogen or C1-C10 alkyl), S, Se or Te, and / or R bb and R cc R dd and R ee R ff and R gg and R hh and R ii Each pair can be connected to each other to provide a ring structure, and

[0321] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0322] In some exemplary embodiments, in formulas 2A-45 to 2A-48, the aromatic ring CH (except as Y) 4 (In addition to CH) can be replaced by N, and one or more (e.g., 1, 2 or 3) N may be included in an aromatic ring.

[0323] In some exemplary embodiments, a compound of chemical formula 1 may be represented by chemical formula 2B.

[0324] [Chemical Formula 2B]

[0325]

[0326] In chemical formula 2B,

[0327] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1,

[0328] Y 1 -Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0329] X 3 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g - or -CR ff R gg -, where R a1 R a2 R b R c R d R e R f and R gEach of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R ee R ff and R gg Each can be independently defined as (CH2) where u is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6). u R u (where R) u (is hydrogen or C1-C10 alkyl) or heteroatoms O, N, S, Se or Te, and / or R bb and R cc R dd and R ee and R ff and R gg Each pair can be connected to each other to provide a ring structure.

[0330] In some example implementations, in chemical formula 2B, Y 4 Can be N or CR k , where R k It is a halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl. In this case, Y 4 N, X 1 And Ar 3 The functional groups (C=O, C=S, C=Se, or C=Te) enhance intramolecular interactions, thereby increasing the absorption intensity at a specific wavelength.

[0331] In some example implementations, in chemical formula 2B, Y 5 Can be N or CR k , where R k It is a halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl, and X 2 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1 -、-(C(R m)=C(R n ))-、or-(C(R) p )=N)-, where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each can be independently halogenated, C1-C20 haloalkyl, or C1-C20 cyanoalkyl, and -(CR f R g ) n1 - n1 can be 1 or 2. In this case, Y 5 and X 2 It can enhance intramolecular interactions, thereby improving the absorption intensity at specific wavelengths.

[0332] In some example implementations, in chemical formula 2B, X 3 (-NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e - or -CR f R g -) and carbon (C) can be linked together to provide a fused ring. This structure can be represented by the chemical formula 2B-1.

[0333] [Chemical Formula 2B-1]

[0334]

[0335] In chemical formula 2B-1,

[0336] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0337] X 31 It can be N, B, or SiR b GeR d CR f , Si, Ge, or C, where R b R d and R fEach of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy.

[0338] Y 1 -Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0339] Cy can be a substituted or unsubstituted C6-C30 aromatic group, such as a substituted or unsubstituted C6-C20 aromatic group, or a substituted or unsubstituted C6-C10 aromatic group; a substituted or unsubstituted C3-C30 heteroaromatic group, such as a substituted or unsubstituted C3-C20 heteroaromatic group, or a substituted or unsubstituted C3-C10 heteroaromatic group; a substituted or unsubstituted C5-C30 cycloalkenyl group, such as a substituted or unsubstituted C5-C20 cycloalkenyl group, or a substituted or unsubstituted C5-C10 cycloalkenyl group; a substituted or unsubstituted C3-C30 heterocyclic alkene group, such as a substituted or unsubstituted C5-C30 heterocyclic alkene group, a substituted or unsubstituted C5-C20 heterocyclic alkene group, or a substituted or unsubstituted C5-C10 heterocyclic alkene group; or a fused ring thereof.

[0340] In some example implementations, in chemical formula 2B, Y 1 (CR k The carbon atoms (C) and carbon atoms (B) can be linked together to provide a fused ring. This structure can be represented by the chemical formula 2B-2.

[0341] [Chemical Formula 2B-2]

[0342]

[0343] In chemical formula 2B-2,

[0344] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0345] X 3 and Y 5 Same as in chemical formula 2B,

[0346] Y 2 -Y 4 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0347] Cy can be a substituted or unsubstituted C6-C30 aromatic group, such as a substituted or unsubstituted C6-C20 aromatic group, or a substituted or unsubstituted C6-C10 aromatic group; a substituted or unsubstituted C3-C30 heteroaromatic group, such as a substituted or unsubstituted C3-C20 heteroaromatic group, or a substituted or unsubstituted C3-C10 heteroaromatic group; a substituted or unsubstituted C5-C30 cycloalkenyl group, such as a substituted or unsubstituted C5-C20 cycloalkenyl group, or a substituted or unsubstituted C5-C10 cycloalkenyl group; a substituted or unsubstituted C3-C30 heterocyclic alkene group, such as a substituted or unsubstituted C5-C30 heterocyclic alkene group, a substituted or unsubstituted C5-C20 heterocyclic alkene group, or a substituted or unsubstituted C5-C10 heterocyclic alkene group; or a fused ring thereof.

[0348] In some exemplary embodiments, the Cy group in Formula 2B-1 and Formula 2B-2 may be an aromatic group, a heteroaromatic group, a cycloalkenyl group, or a heterocyclic alkenyl group, and they may have a 5- to 10-membered ring structure. The heteroaromatic group or heterocyclic alkenyl group may include N in the ring.

[0349] When Cy of chemical formula 2B-1 has a 6-membered ring structure, the compound of chemical formula 2B-1 can be represented by chemical formula 2B-11a.

[0350] [Chemical Formula 2B-11a]

[0351]

[0352] In chemical formula 2B-11a,

[0353] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0354] Y 5 Same as in chemical formula 2B,

[0355] X 33 It can be N, B, or SiR b GeR d , or CR f , where R b R d and R f Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy.

[0356] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0357] In some exemplary embodiments, the CH in the 6-membered ring structure (e.g., a benzene ring and / or a cyclohexadiene ring) of chemical formula 2B-11a may be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0358] When Cy of chemical formula 2B-2 has a 6-membered ring structure, compounds of chemical formula 2B-2 can be represented by chemical formula 2B-21a.

[0359] [Chemical Formula 2B-21a]

[0360]

[0361] In chemical formula 2B-21a,

[0362] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0363] X 3 and Y 5 Same as in chemical formula 2B, and

[0364] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0365] In some exemplary embodiments, the CH in the 6-membered ring structure (e.g., a benzene ring and / or a cyclohexadiene ring) of chemical formula 2B-21a may be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0366] In some example implementations, in chemical formula 2B, Y 1 (CR k X and carbon (C) can be linked together to provide a first fused ring, and X 3 (-NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e - or -CR f R g -) and carbon (C) can be linked together to provide a second fused ring. When the first fused ring and the second fused ring each have a 6-membered ring structure, it can be represented by the chemical formula 2B-3a.

[0367] [Chemical formula 2B-3a]

[0368]

[0369] In chemical formula 2B-3a,

[0370] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0371] Y 5 Same as in chemical formula 2B,

[0372] X 33 It can be N, B, or SiR b GeR d , or CR f , where R b R d and R f Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy.

[0373] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0374] In some exemplary embodiments, the CH in the 6-membered ring structure (e.g., the benzene ring and / or the cyclohexadiene ring) of chemical formula 2B-3a may be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0375] In some example implementations, in chemical formula 2B, when Y 1 -Y 4 For CR k And adjacent R k When connected to each other to provide fused rings (substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, substituted or unsubstituted C5-C30 cycloalkenes, substituted or unsubstituted C3-C30 heterocyclic alkenes, or combinations thereof), they may be represented by one of chemical formulas 2B-41 to 2B-44.

[0376]

[0377] In chemical formulas 2B-41 to 2B-44

[0378] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0379] X 3 and Y 5 Same as in chemical formula 2B,

[0380] X 4 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g-、-CR ff R gg -、-CR h =CR i - or -CR hh =CR ii -, where R a1 R a2 R b R c R d R e R f R g R h and R i Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R ee R ff R gg R hh and R ii Each can be independently defined as (CH2) where t is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6). t Or heteroatoms O, NR t (where R) t (is hydrogen or C1-C10 alkyl), S, Se or Te, and / or R bb and R cc R dd and R ee R ff and R gg and R hh and R ii Each pair can be connected to each other to provide a ring structure, and

[0381] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0382] In some exemplary embodiments, in chemical formulas 2B-41 to 2B-44, the CH of the aromatic ring may be replaced by N, and an aromatic ring may include one or more (e.g., 1, 2, or 3) N.

[0383] In some example implementations, in chemical formula 2B, when X 3 and Y 5 When connected to each other to provide fused rings (substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, substituted or unsubstituted C5-C30 cycloalkenyl groups, substituted or unsubstituted C3-C30 heterocyclic alkenyl groups, or combinations thereof), they may be represented by one of chemical formulas 2B-45 to 2B-50.

[0384]

[0385]

[0386] In chemical formulas 2B-45 to 2B-50

[0387] X 1 X 2 Ar 3 R 11 R 12 R 1 and R 2 Same as in chemical formula 1,

[0388] X 33 It can be N, B, or SiR b GeR d , or CR f , where R b R d and R f Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy.

[0389] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0390] In some exemplary embodiments, in chemical formulas 2B-45 to 2B-50, the CH of the aromatic ring may be replaced by N, and an aromatic ring may include one or more (e.g., 1, 2, or 3) N.

[0391] In some exemplary embodiments, compounds of chemical formula 1 may be represented by chemical formula 2C.

[0392] [Chemical formula 2C]

[0393]

[0394] In chemical formula 2C,

[0395] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0396] Y 1 -Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings.

[0397] X 3 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g - or -CR ff R gg -, where R a1 R a2 R b R c R d R e R f and R g Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R eeR ff and R gg Each can be independently defined as (CH2) where u is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6). u Or heteroatoms O, NR u (where R) u (is hydrogen or C1-C10 alkyl), S, Se or Te, and / or R bb and R cc R dd and R ee and R ff and R gg Each pair can be connected to each other to provide a ring structure.

[0398] In some example implementations, in chemical formula 2C, Y 4 Can be N or CR k , where R k It is a halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl. In this case, Y 4 N, X 1 And Ar 3 The functional groups (C=O, C=S, C=Se, or C=Te) enhance intramolecular interactions, thereby increasing the absorption intensity at a specific wavelength.

[0399] In some example implementations, in chemical formula 2C, X 3 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e - or -CR f R g -, where R a1 R a2 R b R c R d R e R f and R g Each can be independently a halogen, a C1-C20 haloalkyl, or a C1-C20 cyanoalkyl, and X 2 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c-、-GeR d R e -、-(CR f R g ) n1 -、-(C(R m )=C(R n ))-、or-(C(R) p )=N)-, where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each can be independently halogenated, C1-C20 haloalkyl, or C1-C20 cyanoalkyl, and -(CR f R g ) n1 - n1 can be 1 or 2. In this case, X 3 and X 2 It can enhance intramolecular interactions, thereby improving the absorption intensity at specific wavelengths.

[0400] In some example implementations, in chemical formula 2C, when Y 5 For CR k At that time, Y 5 Carbon (C) atoms can be linked together to provide fused rings. This structure can be represented by the chemical formula 2C-1.

[0401] [Chemical formula 2C-1]

[0402]

[0403] In chemical formula 2C-1,

[0404] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0405] X 3 Same as in chemical formula 2C,

[0406] Y 1 -Y 4 Each can be N or CR independently. k , where R kIt can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0407] Cy can be a substituted or unsubstituted C6-C30 aromatic group, such as a substituted or unsubstituted C6-C20 aromatic group, or a substituted or unsubstituted C6-C10 aromatic group; a substituted or unsubstituted C3-C30 heteroaromatic group, such as a substituted or unsubstituted C3-C20 heteroaromatic group, or a substituted or unsubstituted C3-C10 heteroaromatic group; a substituted or unsubstituted C5-C30 cycloalkenyl group, such as a substituted or unsubstituted C5-C20 cycloalkenyl group, or a substituted or unsubstituted C5-C10 cycloalkenyl group; a substituted or unsubstituted C3-C30 heterocyclic alkene group, such as a substituted or unsubstituted C5-C30 heterocyclic alkene group, a substituted or unsubstituted C5-C20 heterocyclic alkene group, or a substituted or unsubstituted C5-C10 heterocyclic alkene group; or a fused ring thereof.

[0408] In some example implementations, in chemical formula 2C, when Y 1 For CR k At that time, Y 1 Carbon (C) atoms can be linked together to provide fused rings. This structure can be represented by the chemical formula 2C-2.

[0409] [Chemical formula 2C-2]

[0410]

[0411] In the chemical formula 2C-2,

[0412] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0413] X 3 and Y 5 Same as in chemical formula 2C,

[0414] Y 2 -Y 4 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R kThey can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0415] Cy can be a substituted or unsubstituted C6-C30 aromatic group, such as a substituted or unsubstituted C6-C20 aromatic group, or a substituted or unsubstituted C6-C10 aromatic group; a substituted or unsubstituted C3-C30 heteroaromatic group, such as a substituted or unsubstituted C3-C20 heteroaromatic group, or a substituted or unsubstituted C3-C10 heteroaromatic group; or a fused ring thereof.

[0416] In some exemplary embodiments, the Cy group of formulas 2C-1 and 2C-2 may be an aromatic group, a heteroaromatic group, a cycloalkenyl group, or a heterocyclic alkenyl group, and they may have a 5- to 10-membered ring structure. The heteroaromatic group or heterocyclic alkenyl group may include N in the ring.

[0417] When Cy of chemical formula 2C-1 has a 6-membered ring structure, compounds of chemical formula 2C-1 can be represented by chemical formula 2C-11a.

[0418] [Chemical formula 2C-11a]

[0419]

[0420] In chemical formula 2C-11a,

[0421] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0422] X 3 Same as in chemical formula 2C, and

[0423] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0424] In some exemplary embodiments, the CH in the 6-membered ring structure (e.g., a benzene ring and / or a cyclohexadiene ring) of chemical formula 2C-11a may be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0425] When Cy of chemical formula 2C-2 has a 6-membered ring structure, compounds of chemical formula 2C-2 can be represented by chemical formula 2C-21a.

[0426] [Chemical formula 2C-21a]

[0427]

[0428] In chemical formula 2C-21a,

[0429] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0430] X 3 and Y 5 Same as in chemical formula 2C, and

[0431] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0432] In some exemplary embodiments, the CH in the 6-membered ring structure (e.g., a benzene ring and / or a cyclohexadiene ring) of chemical formula 2C-21a may be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0433] In some example implementations, in chemical formula 2C, Y 5 (CR k Y and carbon (C) can be linked together to provide a first fused ring, and Y 1 (CR k The first fused ring and carbon (C) can be linked together to provide a second fused ring. When both the first and second fused rings have a 6-membered ring structure, they can be represented by the chemical formula 2C-3a.

[0434] [Chemical formula 2C-3a]

[0435]

[0436] In chemical formula 2C-3a,

[0437] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0438] X 3 Same as in chemical formula 2C, and

[0439] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0440] In some exemplary embodiments, the CH in the 6-membered ring structure (e.g., a benzene ring and / or a cyclohexadiene ring) of chemical formula 2C-3a may be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0441] In chemical formula 2C, when Y 1 -Y 4 For CR k And adjacent R k When connected to each other to provide fused rings (substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, substituted or unsubstituted C5-C30 cycloalkenes, substituted or unsubstituted C3-C30 heterocyclic alkenes, or combinations thereof), they may be represented by one of the chemical formulas 2C-41 to 2C-44.

[0442]

[0443]

[0444] In chemical formulas 2C-41 to 2C-44

[0445] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0446] X 3 and Y 5 Same as in chemical formula 2C,

[0447] X 4 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CRf R g -、-CR ff R gg -、-CR h =CR i - or -CR hh =CR ii -, where R a1 R a2 R b R c R d R e R f R g R h and R i Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R ee R ff R gg R hh and R ii Each can be independently defined as (CH2) where t is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6). t Or heteroatoms O, NR t (where R) t (is hydrogen or C1-C10 alkyl), S, Se or Te, and / or R bb and R cc R dd and R ee R ff and R gg and R hh and R ii Each pair can be connected to each other to provide a ring structure.

[0448] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0449] In some exemplary embodiments, in chemical formulas 2C-41 to 2C-44, the CH of the aromatic ring may be replaced by N and an aromatic ring may include one or more (e.g., 1, 2, or 3) N.

[0450] In chemical formula 2C, when X 3 and Y 5 When connected to each other to provide fused rings (substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, substituted or unsubstituted C5-C30 cycloalkenes, substituted or unsubstituted C3-C30 heterocyclic alkenes, or combinations thereof), they may be represented by one of the chemical formulas 2C-45 to 2C-50.

[0451]

[0452] In chemical formulas 2C-45 to 2C-50

[0453] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0454] X 33 It can be N, B, or SiR b GeR d , or CR f , where R b R d and R f Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy.

[0455] X 4 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g -、-CR ff R gg -、-CR h =CR i - or -CR hh =CRii -, where R a1 R a2 R b R c R d R e R f R g R h and R i Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R ee R ff R gg R hh and R ii Each can be independently defined as (CH2) where t is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6). t Or heteroatoms O, NR t (where R) t (is hydrogen or C1-C10 alkyl), S, Se or Te, and / or R bb and R cc R dd and R ee R ff and R gg and R hh and R ii Each pair can be connected to each other to provide a ring structure, and

[0456] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0457] In some exemplary embodiments, in chemical formulas 2C-45 to 2C-50, the CH of the aromatic ring may be replaced by N, and an aromatic ring may include one or more (e.g., 1, 2, or 3) N.

[0458] In some exemplary embodiments, compounds of chemical formula 1 may be represented by chemical formula 2D.

[0459] [Chemical Formula 2D]

[0460]

[0461] In chemical formula 2D,

[0462] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0463] Y 1 -Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0464] X 3 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g - or -CR ff R gg -, where R a1 R a2 R b R c R d R e R f and R g Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R eeR ff and R gg Each can be independently defined as (CH2) where u is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6). u Or heteroatoms O, NR u (where R) u (is hydrogen or C1-C10 alkyl), S, Se or Te, and / or R bb and R cc R dd and R ee and R ff and R gg Each pair can be connected to each other to provide a ring structure.

[0465] In some example implementations, in chemical formula 2D, Y 4 Can be N or CR k , where R k It can be halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl. In this case, Y 4 N, X 1 And Ar 3 The functional groups (C=O, C=S, C=Se, or C=Te) enhance intramolecular interactions, thereby increasing the absorption intensity at a specific wavelength.

[0466] In some example implementations, in chemical formula 2D, Y 3 Can be N or CR k , where R k It can be halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl, and X 2 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1 -、-(C(R m )=C(R n ))-、or-(C(R) p )=N)-, where R a1 R a2 R b R c R d R e R f Rg R m R n and R p Each can be independently halogenated, C1-C20 haloalkyl, or C1-C20 cyanoalkyl, and -(CR f R g ) n1 - n1 can be 1 or 2. In this case, Y 3 and X 2 It can enhance intramolecular interactions, thereby improving the absorption intensity at specific wavelengths.

[0467] In some example implementations, in chemical formula 2D, when Y 1 For CR k At that time, Y 1 Carbon (C) atoms can be linked together to provide fused rings. This structure can be represented by the chemical formula 2D-1.

[0468] [Chemical formula 2D-1]

[0469]

[0470] In chemical formula 2D-1,

[0471] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0472] X 3 Same as in chemical formula 2D,

[0473] Y 2 -Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0474] Cy can be a substituted or unsubstituted C6-C30 aromatic group, such as a substituted or unsubstituted C6-C20 aromatic group, or a substituted or unsubstituted C6-C10 aromatic group; a substituted or unsubstituted C3-C30 heteroaromatic group, such as a substituted or unsubstituted C3-C20 heteroaromatic group, or a substituted or unsubstituted C3-C10 heteroaromatic group; a substituted or unsubstituted C5-C30 cycloalkenyl group, such as a substituted or unsubstituted C5-C20 cycloalkenyl group, or a substituted or unsubstituted C5-C10 cycloalkenyl group; a substituted or unsubstituted C3-C30 heterocyclic alkene group, such as a substituted or unsubstituted C5-C30 heterocyclic alkene group, a substituted or unsubstituted C5-C20 heterocyclic alkene group, or a substituted or unsubstituted C5-C10 heterocyclic alkene group; or a fused ring thereof.

[0475] In some example implementations, in chemical formula 2D, X 3 (-NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e - or -CR f R g -) and carbon (C) can be linked together to provide a fused ring. This structure can be represented by the chemical formula 2D-2.

[0476] [Chemical formula 2D-2]

[0477]

[0478] In the chemical formula 2D-2,

[0479] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0480] X 31 It can be N, B, or SiR b GeR d CR f , Si, Ge, or C, where R b R d and R f Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy.

[0481] Y 1 -Y5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0482] Cy can be a substituted or unsubstituted C6-C30 aromatic group, such as a substituted or unsubstituted C6-C20 aromatic group, or a substituted or unsubstituted C6-C10 aromatic group; a substituted or unsubstituted C3-C30 heteroaromatic group, such as a substituted or unsubstituted C3-C20 heteroaromatic group, or a substituted or unsubstituted C3-C10 heteroaromatic group; a substituted or unsubstituted C5-C30 cycloalkenyl group, such as a substituted or unsubstituted C5-C20 cycloalkenyl group, or a substituted or unsubstituted C5-C10 cycloalkenyl group; a substituted or unsubstituted C3-C30 heterocyclic alkene group, such as a substituted or unsubstituted C5-C30 heterocyclic alkene group, a substituted or unsubstituted C5-C20 heterocyclic alkene group, or a substituted or unsubstituted C5-C10 heterocyclic alkene group; or a fused ring thereof.

[0483] In some exemplary embodiments, the Cy group of formulas 2D-1 and 2D-2 may be an aromatic group, a heteroaromatic group, a cycloalkenyl group, or a heterocyclic alkenyl group, and they may have a 5- to 10-membered ring structure. The heteroaromatic group or heterocyclic alkenyl group may include N in the ring.

[0484] When Cy of chemical formula 2D-1 has a 6-membered ring structure, the compound of chemical formula 2D-1 can be represented by chemical formula 2D-11a.

[0485] [Chemical formula 2D-11a]

[0486]

[0487] In chemical formula 2D-11a,

[0488] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0489] X 3 Same as in chemical formula 2D,

[0490] Y 4 and Y 5 Each can be N or CR independently.k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0491] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0492] In some exemplary embodiments, the CH in the 6-membered ring structure (e.g., a benzene ring and / or a cyclohexadiene ring) of chemical formula 2D-11a may be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0493] When Cy of chemical formula 2D-2 has a 6-membered ring structure, compounds of chemical formula 2D-2 can be represented by chemical formula 2D-21a.

[0494] [Chemical formula 2D-21a]

[0495]

[0496] In chemical formula 2D-21a,

[0497] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0498] Y 4 and Y 5 Same as in chemical formula 2D,

[0499] X 33 It can be N, B, or SiR b GeR d , or CR f , where R b R d and R f Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy.

[0500] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0501] In some exemplary embodiments, the CH in the 6-membered ring structure (e.g., a benzene ring and / or a cyclohexadiene ring) of chemical formula 2D-21a may be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0502] In some example implementations, in chemical formula 2D, Y 1 (CR k X and carbon (C) can be linked together to provide a first fused ring, and X 3 (-NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e - or -CR f R g -) and carbon (C) can be linked together to provide a second fused ring. When the first fused ring and the second fused ring each have a 6-membered ring structure, it can be represented by the chemical formula 2D-3a.

[0503] [Chemical formula 2D-3a]

[0504]

[0505] In chemical formula 2D-3a,

[0506] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0507] X 33 It can be N, B, or SiR b GeR d , or CR f , where R b R d and R f Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy.

[0508] Y4 and Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be connected to each other to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings.

[0509] In some exemplary embodiments, the CH in the 6-membered ring structure (e.g., a benzene ring and / or a cyclohexadiene ring) of chemical formula 2D-3a may be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0510] In chemical formula 2D, when X 3 and Y 5 Or Y 4 and Y 5 When connected to each other to provide fused rings (substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, substituted or unsubstituted C5-C30 cycloalkenes, substituted or unsubstituted C3-C30 heterocyclic alkenes, or combinations thereof), they may be represented by one of the chemical formulas 2D-41 to 2D-46.

[0511]

[0512]

[0513] In chemical formulas 2D-41 to 2D-46

[0514] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0515] X 33 It can be N, B, or SiR b GeR d , or CR f , where R b R d and R fEach of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy.

[0516] X 4 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g -、-CR ff R gg -、-CR h =CR i - or -CR hh =CR ii -, where R a1 R a2 R b R c R d R e R f R g R h and R i Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R ee R ff R gg R hh and R ii Each can be independently defined as (CH2) where t is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6). t Or heteroatoms O, NR t (where R) t (is hydrogen or C1-C10 alkyl), S, Se or Te, and / or R bb and R cc Rdd and R ee R ff and R gg and R hh and R ii Each pair can be connected to each other to provide a ring structure, and

[0517] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0518] In some exemplary embodiments, in chemical formulas 2D-41 to 2D-46, the CH of the aromatic ring may be replaced by N, and an aromatic ring may include one or more (e.g., 1, 2, or 3) N.

[0519] In chemical formula 2D, when Y 1 -Y 3 When two adjacent rings are connected to each other to provide a fused ring (a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C3-C30 heterocyclic alkene group, or a combination thereof), it may be represented by one of the chemical formulas 2D-47 to 2D-50.

[0520]

[0521] In chemical formulas 2D-47 to 2D-50

[0522] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0523] X 3 Y 4 and Y 5 Same as in chemical formula 2D,

[0524] X 4 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc-、-GeR d R e -、-GeR dd R ee -、-CR f R g -、-CR ff R gg -、-CR h =CR i - or -CR hh =CR ii -, where R a1 R a2 R b R c R d R e R f R g R h and R i Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R ee R ff R gg R hh and R ii Each can be independently defined as (CH2) where t is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6). t Or heteroatoms O, NR t (where R) t (is hydrogen or C1-C10 alkyl), S, Se or Te, and / or R bb and R cc R dd and R ee R ff and R gg and R hh and R ii Each pair can be connected to each other to provide a ring structure, and

[0525] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0526] In some exemplary embodiments, in chemical formulas 2D-47 to 2D-50, the CH of the aromatic ring may be replaced by N, and an aromatic ring may include one or more (e.g., 1, 2, or 3) N.

[0527] In some exemplary embodiments, compounds of chemical formula 1 may be represented by chemical formula 2E.

[0528] [Chemical formula 2E]

[0529]

[0530] In chemical formula 2E,

[0531] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0532] Y 1 -Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0533] X 3 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g - or -CR ff R gg -, where R a1 R a2 R b R c R d R eR f and R g Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R ee R ff and R gg Each can be independently defined as (CH2) where u is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6). u Or heteroatoms O, NR u (where R) u (is hydrogen or C1-C10 alkyl), S, Se or Te, and / or R bb and R cc R dd and R ee and R ff and R gg Each pair can be connected to each other to provide a ring structure.

[0534] In some example implementations, in chemical formula 2E, X 3 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e - or -CR f R g -, where R a1 R a2 R b R c R d R e R f and R g Each can be independently a halogen, a C1-C20 haloalkyl, or a C1-C20 cyanoalkyl. In this case, X 3 N, X 1 And Ar 3 The functional groups (C=O, C=S, C=Se, or C=Te) enhance intramolecular interactions, thereby increasing the absorption intensity at a specific wavelength.

[0535] In some example implementations, in chemical formula 2E, Y3 Can be N or CR k , where R k It can be halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl, and X 2 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1 -、-(C(R m )=C(R n ))-、or-(C(R) p )=N)-, where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each can be independently halogenated, C1-C20 haloalkyl, or C1-C20 cyanoalkyl, and -(CR f R g ) n1 - n1 can be 1 or 2. In this case, Y 3 and X 2 It can enhance intramolecular interactions, thereby improving the absorption intensity at specific wavelengths.

[0536] In some example implementations, in chemical formula 2E, Y 1 (CR k The carbon atoms (C) and carbon atoms (B) can be linked together to provide a fused ring. This structure can be represented by the chemical formula 2E-1.

[0537] [Chemical formula 2E-1]

[0538]

[0539] In chemical formula 2E-1,

[0540] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0541] X 3 Same as in chemical formula 2E,

[0542] Y 2 -Y 5 Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0543] Cy can be a substituted or unsubstituted C6-C30 aromatic group, such as a substituted or unsubstituted C6-C20 aromatic group, or a substituted or unsubstituted C6-C10 aromatic group; a substituted or unsubstituted C3-C30 heteroaromatic group, such as a substituted or unsubstituted C3-C20 heteroaromatic group, or a substituted or unsubstituted C3-C10 heteroaromatic group; a substituted or unsubstituted C5-C30 cycloalkenyl group, such as a substituted or unsubstituted C5-C20 cycloalkenyl group, or a substituted or unsubstituted C5-C10 cycloalkenyl group; a substituted or unsubstituted C3-C30 heterocyclic alkene group, such as a substituted or unsubstituted C5-C30 heterocyclic alkene group, a substituted or unsubstituted C5-C20 heterocyclic alkene group, or a substituted or unsubstituted C5-C10 heterocyclic alkene group; or a fused ring thereof.

[0544] In some example implementations, in chemical formula 2E, Y 4 (CR k The carbon atoms (C) and carbon atoms (B) can be linked together to provide a fused ring. This structure can be represented by the chemical formula 2E-2.

[0545] [Chemical formula 2E-2]

[0546]

[0547] In chemical formula 2E-2,

[0548] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0549] X 3 Same as in chemical formula 2E,

[0550] Y 1 -Y 3 and Y 5Each can be N or CR independently. k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0551] Cy can be a substituted or unsubstituted C6-C30 aromatic group, such as a substituted or unsubstituted C6-C20 aromatic group, or a substituted or unsubstituted C6-C10 aromatic group; a substituted or unsubstituted C3-C30 heteroaromatic group, such as a substituted or unsubstituted C3-C20 heteroaromatic group, or a substituted or unsubstituted C3-C10 heteroaromatic group; a substituted or unsubstituted C5-C30 cycloalkenyl group, such as a substituted or unsubstituted C5-C20 cycloalkenyl group, or a substituted or unsubstituted C5-C10 cycloalkenyl group; a substituted or unsubstituted C3-C30 heterocyclic alkene group, such as a substituted or unsubstituted C5-C30 heterocyclic alkene group, a substituted or unsubstituted C5-C20 heterocyclic alkene group, or a substituted or unsubstituted C5-C10 heterocyclic alkene group; or a fused ring thereof.

[0552] In some exemplary embodiments, the Cy group of formulas 2E-1 and 2E-2 may be an aromatic group, a heteroaromatic group, a cycloalkenyl group, or a heterocyclic alkenyl group, and they may have a 5- to 10-membered ring structure. The heteroaromatic group or heterocyclic alkenyl group may include N in the ring.

[0553] When Cy of chemical formula 2E-1 has a 6-membered ring structure, the compound of chemical formula 2E-1 can be represented by chemical formula 2E-11a.

[0554] [Chemical formula 2E-11a]

[0555]

[0556] In chemical formula 2E-11a,

[0557] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0558] X 3 Y 4 and Y 5 Same as in chemical formula 2E,

[0559] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0560] In some exemplary embodiments, the CH in the 6-membered ring structure (e.g., a benzene ring and / or a cyclohexadiene ring) of chemical formula 2E-11a may be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0561] When Cy of chemical formula 2E-2 has a 6-membered ring structure, the compound of chemical formula 2E-2 can be represented by chemical formula 2E-21a.

[0562] [Chemical formula 2E-21a]

[0563]

[0564] In chemical formula 2E-21a,

[0565] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0566] X 3 and Y 5 Same as in chemical formula 2E, and

[0567] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0568] In some exemplary embodiments, the CH in the 6-membered ring structure (e.g., a benzene ring and / or a cyclohexadiene ring) of chemical formula 2E-21a may be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0569] In some example implementations, in chemical formula 2E, Y 1 (CR k Y and carbon (C) can be linked together to provide a first fused ring, and Y 4 (CR k The first fused ring and carbon (C) can be linked together to provide a second fused ring. When the first fused ring and the second fused ring each have a 6-membered ring structure, it can be represented by the chemical formula 2E-3a.

[0570] [Chemical formula 2E-3a]

[0571]

[0572] In chemical formula 2E-3a,

[0573] X 1 X 2 Ar 3 R 1 and R 2 Same as in chemical formula 1,

[0574] X 3 Same as in chemical formula 2E,

[0575] Y 5 Can be N or CR k , where R k It can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or adjacent R k They can be linked together to provide substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, or their fused rings, and

[0576] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0577] In some exemplary embodiments, the CH in the 6-membered ring structure (e.g., the benzene ring and / or the cyclohexadiene ring) of chemical formula 2E-3a may be replaced by N, and a 6-membered ring structure may include one or more (e.g., 1, 2, or 3) N.

[0578] In some example implementations, in chemical formula 2E, when Y 4 and Y 5 Or Y 5 and X 3 When connected to each other to provide fused rings (substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, substituted or unsubstituted C5-C30 cycloalkenyl groups, substituted or unsubstituted C3-C30 heterocyclic alkenyl groups, or combinations thereof), they may be represented by one of chemical formulas 2E-41 to 2E-46.

[0579]

[0580]

[0581] In chemical formulas 2E-41 to 2E-46

[0582] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0583] X 33 It can be N, B, or SiR b GeR d , or CR f , where R b R d and R f Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy.

[0584] X 3 and Y 4 Same as in chemical formula 2E,

[0585] X 4 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g -、-CR ff R gg -、-CR h =CR i - or -CR hh =CR ii -, where R a1 R a2 R b R c R d R e R f R g R h and Ri Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R ee R ff R gg R hh and R ii Each can be independently defined as (CH2) where t is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6). t Or heteroatoms O, NR t (where R) t (is hydrogen or C1-C10 alkyl), S, Se or Te, and / or R bb and R cc R dd and R ee R ff and R gg and R hh and R ii Each pair connects to each other to provide a ring structure, and

[0586] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0587] In some exemplary embodiments, in chemical formulas 2E-41 to 2E-46, the CH of the aromatic ring may be replaced by N, and an aromatic ring may include one or more (e.g., 1, 2, or 3) N.

[0588] In some example implementations, in chemical formula 2E, when Y 1 -Y 3 For CR k And adjacent R k When connected to each other to provide fused rings (substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C3-C30 heteroaromatic groups, substituted or unsubstituted C5-C30 cycloalkenyl groups, substituted or unsubstituted C3-C30 heterocyclic alkenyl groups, or combinations thereof), they may be represented by one of chemical formulas 2E-47 to 2E-50.

[0589]

[0590]

[0591] In chemical formulas 2E-47 to 2E-50

[0592] X 1 X 2 Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0593] X 3 Y 4 and Y 5 Same as in chemical formula 2E,

[0594] X 4 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g -、-CR ff R gg -、-CR h =CR i - or -CR hh =CR ii -, where R a1 R a2 R b R c R d R e R f R g R h and R i Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb R cc R dd R ee R ffR gg R hh and R ii Each can be independently defined as (CH2) where t is a positive integer (e.g., any integer with a value of 1 or greater, 1-10, 1-8, or 1-6). t Or heteroatoms O, NR t (where R) t (is hydrogen or C1-C10 alkyl), S, Se or Te, and / or R bb and R cc R dd and R ee R ff and R gg and R hh and R ii Each pair connects to each other to provide a ring structure, and

[0595] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0596] In some exemplary embodiments, in chemical formulas 2E-47 to 2E-50, the CH of the aromatic ring may be replaced by N, and an aromatic ring may include one or more (e.g., 1, 2, or 3) N.

[0597] In chemical formula 1, X 1 X 2 、 and -CR 11 R 12 -and X of chemical formulas 2B, 2C, 2D, and 2E. 3 In this context, the ring structure can be a spirocyclic structure or a fused ring structure. The spirocyclic structure can be a substituted or unsubstituted C5-C30 hydrocarbon ring group, a substituted or unsubstituted C2-C30 heterocyclic group, or a fused ring thereof. The substituted or unsubstituted C5-C30 hydrocarbon ring group can be, for example, a substituted or unsubstituted C5-C30 cycloalkyl group (e.g., a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C10 cycloalkyl group). Examples of the fused ring include fluorenyl and indaneyl groups. The substituted or unsubstituted C2-C30 heterocyclic group can be, for example, a substituted or unsubstituted C2-C30 heterocyclic alkyl group (e.g., a substituted or unsubstituted C2-C20 heterocyclic alkyl group, or a substituted or unsubstituted C2-C10 heterocyclic alkyl group).

[0598] The fused ring structure may have fused substituted or unsubstituted C5-C30 hydrocarbon ring groups, fused substituted or unsubstituted C2-C30 heterocyclic groups, or fused rings thereof. The substituted or unsubstituted C5-C30 cycloalkyl group may be, for example, a substituted or unsubstituted C5-C30 cycloalkyl group (e.g., a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C10 cycloalkyl group) or a substituted or unsubstituted C6-C30 aryl group (e.g., a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C6-C10 aryl group), and the substituted or unsubstituted C2-C30 heterocyclic group may be, for example, a substituted or unsubstituted C2-C30 heterocyclic alkyl group (e.g., a substituted or unsubstituted C2-C20 heterocyclic alkyl group, or a substituted or unsubstituted C2-C10 heterocyclic alkyl group) or a substituted or unsubstituted C2-C30 heteroaryl group (e.g., a substituted or unsubstituted C2-C20 heteroaryl group, or a substituted or unsubstituted C2-C10 heteroaryl group).

[0599] The spiro-ring structure may include a portion represented by chemical formula 3.

[0600] [Chemical Formula 3]

[0601]

[0602] In chemical formula 3,

[0603] X a and X b They can be independently -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、or-GeR dd R ee -, where R a1 R a2 R b R c R d and R e Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryloxy, or substituted or unsubstituted C3-C20 heteroaryl, and R bb and R cc and R dd and Ree Each pair can be connected to each other to provide a ring structure.

[0604] L a Can be -O-, -S-, -Se-, -Te-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1 -、-(C(R p ) = N)-, or a single bond, where R a1 R a2 R b R c R d R e R f R g and R p Each can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy, and -(CR f R g ) n1 -n1 can be 1 or 2, and

[0605] The hydrogen atoms in each ring may optionally be replaced by at least one substituent selected from the following: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0606] In chemical formula 3, one or more CHs present in the aromatic rings of parts (3), (4), (5), (6), (7), (8), or (9) may be replaced by N.

[0607] In chemical formula 1, Ar 3 It can be represented by chemical formula 4.

[0608] [Chemical Formula 4]

[0609]

[0610] In chemical formula 4,

[0611] Ar 3 It can be a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group.

[0612] Z 1 It can be O, S, Se, or Te, and

[0613] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR a R b At that time, R a and R b At least one of them is a cyano group or a group containing a cyano group.

[0614] In chemical formula 1, Ar 3 It can be a cyclic group represented by one of the chemical formulas 5A to 5F.

[0615] [Chemical Formula 5A]

[0616]

[0617] In chemical formula 5A,

[0618] Z 1 It can be O, S, Se, or Te.

[0619] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR a R b At that time, R a and R b At least one of them is a cyano group or a group containing a cyano group.

[0620] Z 3 Can be N or CR c , where R c It can be hydrogen, deuterium, or a substituted or unsubstituted C1-C10 alkyl group.

[0621] R 11 R 12 R 13 R 14 and R 15Each of these can independently be hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, halogen, cyano (-CN), a cyano-containing group, or a combination thereof, wherein R 12 and R 13 and R 14 and R 15 They can exist independently or connect with each other to provide fused aromatic rings.

[0622] n can be 0 or 1, and

[0623] * Can be a connection point.

[0624] In some example implementations, in chemical formula 5A, CR 11 CR 12 CR 13 CR 14 and CR 15 At least one of them can be replaced by nitrogen (N). That is, the substituted or unsubstituted benzene ring moiety of chemical formula 5A may include a heteroatom (N).

[0625] [Chemical Formula 5B]

[0626]

[0627] In chemical formula 5B,

[0628] Z 1 It can be O, S, Se, or Te.

[0629] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR a R b At that time, R a and R b At least one of them is a cyano group or a group containing a cyano group.

[0630] Z 3 It can be O, S, Se, Te, or C(R) a (CN), where R a It is hydrogen, cyano (-CN), or C1-C10 alkyl.

[0631] R 11 and R 12Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, halogen, cyano (-CN), or a combination thereof, and

[0632] * Can be a connection point.

[0633] [Chemical formula 5C]

[0634]

[0635] In the chemical formula 5C,

[0636] Z 1 It can be O, S, Se, or Te.

[0637] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR a R b At that time, R a and R b At least one of them is a cyano group or a group containing a cyano group.

[0638] R 11 R 12 and R 13 Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, halogen, cyano (-CN), or a combination thereof, and

[0639] * Can be a connection point.

[0640] [Chemical Formula 5D]

[0641]

[0642] In chemical formula 5D,

[0643] Z 1 It can be O, S, Se, or Te.

[0644] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and Rb Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR a R b At that time, R a and R b At least one of them is a cyano group or a group containing a cyano group.

[0645] Z 3 Can be N or CR c , where R c It can be hydrogen or a substituted or unsubstituted C1-C10 alkyl group.

[0646] G 1 It can be O, S, Se, Te, SiR x R y or GeR z R w , where R x R y R z and R w Each can be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, or substituted or unsubstituted C6-C20 aryl.

[0647] R 11 R 12 and R 13 Each of these can independently be hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, halogen, cyano, a cyano-containing group, or a combination thereof, wherein R 12 and R 13 They can exist independently or connect with each other to provide fused aromatic rings.

[0648] n can be 0 or 1, and

[0649] * Can be a connection point.

[0650] [Chemical formula 5E]

[0651]

[0652] In chemical formula 5E,

[0653] Z 1 It can be O, S, Se, or Te.

[0654] Z 2 It can be O, S, Se, Te, or CR a R b , where Ra and R b Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR a R b At that time, R a and R b At least one of them is a cyano group or a group containing a cyano group.

[0655] Z 3 Can be N or CR c , where R c It can be hydrogen or a substituted or unsubstituted C1-C10 alkyl group.

[0656] G 2 It can be O, S, Se, Te, SiR x R y or GeR z R w , where R x R y R z and R w Each can be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, or substituted or unsubstituted C6-C20 aryl.

[0657] R 11 R 12 and R 13 Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, halogen, cyano, cyano-containing groups, or combinations thereof.

[0658] n can be 0 or 1, and

[0659] * Can be a connection point.

[0660] [Chemical formula 5F]

[0661]

[0662] In the chemical formula 5F,

[0663] Z 1 For O, S, Se, or Te,

[0664] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R bEach can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR a R b At that time, R a and R b At least one of them is a cyano group or a group containing a cyano group.

[0665] R 11 It can be hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, halogen, cyano (-CN), a cyano-containing group, or a combination thereof, and

[0666] G 3 It can be O, S, Se, Te, SiR x R y or GeR z R w Among them, R x R y R z and R w Each can be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, or substituted or unsubstituted C6-C20 aryl.

[0667] [Chemical Formula 5G]

[0668]

[0669] In chemical formula 5G,

[0670] Z 1 It can be O, S, Se, or Te, and

[0671] R a and R b Each can be independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a group containing a cyano group, and

[0672] Z 2 -Z 4 Each can be independently O, S, Se, Te, or CR c R d , where R c and R d Each is independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, provided that Z is... 2 For CR c R d At that time, R c and R d At least one of them is a cyano group or a group containing a cyano group.

[0673] The cyclic group represented by chemical formula 5A can be a cyclic group represented by chemical formula 5A-1 or chemical formula 5A-2.

[0674] [Chemical Formula 5A-1]

[0675]

[0676] [Chemical Formula 5A-2]

[0677]

[0678] In chemical formulas 5A-1 and 5A-2,

[0679] Z 3 R 11 n, R 11 R 12 R 13 R 14 and R 15 Same as in chemical formula 5A.

[0680] When R 12 and R 13 and / or R 14 and R 15 When they can be independently linked to form fused aromatic rings, the cyclic group represented by chemical formula 5A can be a cyclic group represented by chemical formula 5A-3.

[0681] [Chemical Formula 5A-3]

[0682]

[0683] In chemical formula 5A-3,

[0684] Z 1 Z 2 Z 3 R 11 The , and n are the same as in chemical formula 5A.

[0685] R 12a and R 12b Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, halogen, cyano (-CN), a cyano-containing group, or a combination thereof.

[0686] m1 and m2 can each be an integer in the range 0-4, and

[0687] Ph 1 and Ph 2 This refers to a fused phenylene ring, and Ph1 and Ph 2 One of them can be omitted at will.

[0688] The cyclic group represented by chemical formula 5B can be, for example, a cyclic group represented by chemical formula 5B-1, 5B-2, or 5B-3.

[0689]

[0690]

[0691] In chemical formulas 5B-1, 5B-2, and 5B-3,

[0692] R 11 and R 12 Same as in chemical formula 5B.

[0693] The cyclic group represented by the chemical formula 5C can be, for example, a cyclic group represented by the chemical formula 5C-1 or 5C-2.

[0694]

[0695] In chemical formulas 5C-1 and 5C-2,

[0696] R 11 -R 13 Same as in chemical formula 5C.

[0697] In chemical formula 1, the electron donor portion N and the portion containing X 1 The ring of X 1 Ar, as an electron acceptor 3 Functional groups (C=O, C=S, C=Se, or C=Te) enhance intramolecular interactions to improve absorption intensity at specific wavelengths.

[0698] Specific examples of compounds represented by chemical formula 2A may include, but are not limited to, compounds of group 1.

[0699] [Group 1]

[0700]

[0701]

[0702] In group 1, Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 1, and

[0703] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0704] In group 1, X in chemical formula 2A is shown. 1 Compounds of the -Se- group, but said -Se- can be X 1 Another linking group (-S-, -Te-, -S(=O)-, -S(=O)2-, -NR) a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g - or -CR ff R gg -)replace.

[0705] In group 1, X in chemical formula 2A is shown. 2 It is a compound of the form -(C(CH3)(CH3))-, but the -(C(CH3)(CH3)) can be X 2 Another linking group (-O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR) a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-(CR f R g ) n1 -、-(CR ff R gg )-、-(C(R m )=C(R n ))-、-(C(R mm )=C(R nn ))-、or-(C(R) p )=N)-) replace.

[0706] Specific examples of compounds represented by chemical formula 2A-1 or chemical formula 2A-2 may include, but are not limited to, compounds of group 1-1.

[0707] [Group 1-1]

[0708]

[0709]

[0710] In group 1-1,

[0711] Ar 3 R 1 and R 2 Same as in chemical formula 1, and

[0712] The hydrogen atoms of each ring (benzene ring or cyclohexadiene ring) may be replaced by at least one substituent selected from the following: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0713] This describes a structure in which the CH in the benzene ring present in group 1-1 is replaced by an N, but the CH in each ring (benzene ring or cyclohexadiene) of group 1-1 can be replaced by N, one of the rings may include one or more N, and multiple rings may contain N.

[0714] In group 1-1, X is shown in chemical formula 2A-1 or chemical formula 2A-2. 1 Compounds of the -Se- group, but said -Se- can be X 1 Another linking group (-S-, -Te-, -S(=O)-, -S(=O)2-, -NR) a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g - or -CR ff R gg -)replace.

[0715] In group 1-1, X is shown in chemical formulas 2A-1 and 2A-2. 2 It is a compound of the form -(C(CH3)(CH3))-, but the -(C(CH3)(CH3)) can be X 2Another linking group (-O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR) a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-(CR f R g ) n1 -、-(CR ff R gg )-、-(C(R m )=C(R n ))-、-(C(R mm )=C(R nn ))-、or-(C(R) p )=N)-) replace.

[0716] Group 1 and Group 1-1 may be examples of compounds represented by chemical formula 2A, but examples of compounds represented by chemical formulas 2B to 2E may also be provided in the same manner.

[0717] For example, specific examples of compounds represented by chemical formula 2E can be provided through compounds in group 2, but are not limited thereto.

[0718] [Group 2]

[0719]

[0720] In group 2,

[0721] Ar 3 R 11 R 12 R 1 and R 2 Same as in chemical formula 1, and

[0722] R a1 R f and R g Each of these can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy, and

[0723] The hydrogen atoms of each aromatic ring may be replaced by at least one of the following substituents: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C6-C20 aryloxy.

[0724] In group 2, X in chemical formula 2E is shown. 1 Compounds of the -Se- group, but said -Se- can be X 1 Another linking group (-S-, -Te-, -S(=O)-, -S(=O)2-, -NR) a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g - or -CR ff R gg -)replace.

[0725] In group 2, X in chemical formula 2E is shown. 2 It is a compound of the form -(C(CH3)(CH3))-, but the -(C(CH3)(CH3)) can be X 2 Another linking group (-O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR) a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-(CR f R g ) n1 -、-(CR ff R gg )-、-(C(R m )=C(R n ))-、-(C(R mm )=C(R nn ))-、or-(C(R) p )=N)-) replace.

[0726] Specific examples of compounds represented by chemical formula 1 may include compounds of group 3.

[0727] [Group 3]

[0728]

[0729]

[0730]

[0731] The n-type semiconductor compound may be phthalocyanine or phthalocyanine derivatives, fullerene or fullerene derivatives, thiophene or thiophene derivatives, or a combination thereof.

[0732] The fullerenes may include C60, C70, C76, C78, ​​C80, C82, C84, C90, C96, C240, C540, mixtures thereof, fullerene nanotubes, etc. The fullerene derivatives may refer to compounds of these fullerenes having their substituents. The fullerene derivatives may include substituents such as alkyl (e.g., C1-C30 alkyl), aryl (e.g., C6-C30 aryl), heterocyclic groups (e.g., C3-C30 heterocyclic alkyl), etc. Examples of aryl and heterocyclic groups may be benzene rings, naphthyl rings, anthracene rings, phenanthrene rings, fluorene rings, benzo[9,10]phenanthrene rings, tetraphenyl rings, biphenyl rings, pyrrole rings, furan rings, thiophene rings, imidazole rings, etc. Azole ring, thiazole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, indazine ring, indole ring, benzofuran ring, benzothiophene ring, isobenzofuran ring, benzimidazole ring, imidazopyridine ring, quinazine ring, quinoline ring, phthalazine ring, naphthidine ring, quinoxaline ring, quinazoline ring, isoquinoline ring, carbazole ring, phenanthridine ring, acridine ring, phenanthrene ring, thiamethoxam ring, chromene ring, xanthonium ring, phenanthrene ring Azine ring, phen Thiazine ring, phenothiazine ring, or phenothiazine ring.

[0733] The phthalocyanine or phthalocyanine derivative may be represented by chemical formula 6.

[0734] [Chemical Formula 6]

[0735]

[0736] In chemical formula 6,

[0737] R 31 -R 33 Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, halogen, halogen-containing group, or a combination thereof.

[0738] a, b, and c are integers in the range 1-3, and

[0739] Z is a monovalent substituent.

[0740] For example, Z can be a halogen or a halogen-containing group, such as F, Cl, a group containing F, or a group containing Cl.

[0741] Halogen refers to F, Cl, Br, or I, and the halogen-containing group refers to an alkyl group (C1-C30 alkyl) in which at least one hydrogen atom is replaced by F, Cl, Br, or I.

[0742] The thiophene derivative may be represented, for example, by chemical formula 7 or 8, but is not limited thereto.

[0743] [Chemical Formula 7]

[0744]

[0745] [Chemical Formula 8]

[0746] EWG-T 1 -T 2 -T 3 -EWG 2

[0747] In chemical formulas 7 and 8,

[0748] T 1 T 2 and T 3 It can be an aromatic ring including substituted or unsubstituted thiophene moieties.

[0749] T 1 T 2 and T 3 They can exist independently or they can merge with each other.

[0750] X 3 -X 8 Each of these can independently be hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heterocyclic group, cyano, cyano-containing group, or a combination thereof, and

[0751] EWG 1 and EWG 2 Each can be an electron-withdrawing group independently.

[0752] For example, in chemical formula 7, X 3 -X 8 At least one of them may be an electron-withdrawing group, such as a group containing a cyano group.

[0753] The composition for use in optoelectronic devices may further include a second p-type semiconductor compound that selectively absorbs green light. The second p-type semiconductor compound may be a compound represented by chemical formula 9.

[0754] [Chemical Formula 9]

[0755]

[0756] In chemical formula 9,

[0757] R 41 -R 43 Each of these can be independently hydrogen, a substituted or unsubstituted C1-C30 aliphatic hydrocarbon group, a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C1-C30 aliphatic heterocyclic group, a substituted or unsubstituted C2-C30 aromatic heterocyclic group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a thiol group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, a cyano group, a cyano-containing group, a halogen, a halogen-containing group, a substituted or unsubstituted sulfonyl group (e.g., a substituted or unsubstituted C0-C30 aminosulfonyl group, a substituted or unsubstituted C1-C30 alkylsulfonyl group, or a substituted or unsubstituted C6-C30 arylsulfonyl group), or a combination thereof, or R 41 -R 43 Two adjacent groups in the ring can connect to each other to provide a fused ring.

[0758] L 1 -L 3 Each of these can be independently a single bond, a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C6-C30 arylene group, a divalent substituted or unsubstituted C3-C30 heterocyclic group, or a combination thereof.

[0759] R 51 -R 53 Each of these can be independently a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted C1-C30 alkoxy, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C3-C30 heterocyclic group, a substituted or unsubstituted amino group (e.g., a substituted or unsubstituted C1-C30 alkylamino, or a substituted or unsubstituted C6-C30 arylamino), a substituted or unsubstituted silyl, or a combination thereof, and

[0760] ac can be an integer in the range 0-4, each of which can be independent.

[0761] Based on 100 parts by weight of the compound represented by chemical formula 1, the second p-type semiconductor compound that selectively absorbs green light may be included in an amount of about 500 to about 1500 parts by weight.

[0762] The composition for optoelectronic devices selectively absorbs light in the green wavelength region and, in a thin-film state, can have a maximum absorption wavelength (λ) in the wavelength regions greater than or equal to about 500 nm, for example, greater than or equal to about 510 nm, greater than or equal to about 520 nm, greater than or equal to about 525 nm, or greater than or equal to about 530 nm and less than or equal to about 600 nm, less than or equal to about 590 nm, for example, less than or equal to about 580 nm, less than or equal to about 570 nm, less than or equal to about 560 nm, less than or equal to about 555 nm, or less than or equal to about 550 nm. 最大 ).

[0763] The composition for optoelectronic devices, in its thin-film state, can exhibit a light absorption profile with a half-width (FWHM) of about 50 nm to about 110 nm, for example, about 50 nm to about 100 nm. Here, FWHM is the width of the wavelength corresponding to half the height of the maximum absorption point. When the FWHM is small, wavelength selectivity is improved by selectively absorbing light in a narrow wavelength region. As used herein, unless otherwise specifically defined, it can be defined by absorbance measured by UV-Vis spectroscopy. When the FWHM is within this range, selectivity in the green wavelength region can be improved. The thin film can be a thin film deposited under vacuum conditions.

[0764] When the composition for optoelectronic devices comprises a compound of formula 1 and C60 in a volume ratio of about 0.9:1 to about 1.1:1, for example about 1:1, the composition may have a content greater than or equal to about 6.0 × 10⁻⁶. 4 cm -1 For example, approximately 6.7 × 10 4 cm -1 - Approximately 10×10 4 cm -1 Or approximately 6.9 × 10 4 cm -1 - Approximately 10×10 4 cm -1 The absorption coefficient.

[0765] In addition, the composition for optoelectronic devices can exhibit improved residual charge characteristics while having high wavelength selectivity (narrow FWHM) and absorption coefficient, thereby reducing the afterimage of the device.

[0766] The composition for the optoelectronic device can be formed into a thin film by co-depositing a p-type semiconductor compound and an n-type semiconductor compound. The deposition method provides a uniform thin film and has a low possibility of impurities being included (trapped) in the film; however, when the compound has a melting point lower than the temperature used for deposition, products from the decomposition of the compound can be deposited, and thus the performance of the device can deteriorate. Therefore, the compound desiccates to have a melting point higher than the deposition temperature. The compound has a melting point, for example, at least about 10°C, for example, at least about 20°C, or at least about 30°C higher than the deposition temperature and is therefore desiccated.

[0767] More specifically, the donor-acceptor type material represented by chemical formula 1 can be described at the melting point (T) of the material. m Thermal decomposition occurs at the melting point (T) because... m ) and decomposition temperature (T) d The temperatures (sublimation temperature, deposition temperature, T) are similar. Therefore, if the temperature at which the film is formed by vacuum deposition (sublimation temperature, deposition temperature, T) is similar... s (Higher than T) m In this case, decomposition occurs more preferentially than sublimation (deposition), and therefore normal devices cannot be fabricated. Since it is impossible to fabricate stable image sensors using these materials, T... m It should be higher than T s And agreeably T m -T s ≥10℃.

[0768] Furthermore, during the fabrication of image sensors, a microlens array (MLA) needs to be formed after the fabrication of organic optoelectronic devices to concentrate light. This microlens array requires relatively high temperatures (greater than or equal to about 160°C, for example, greater than or equal to about 170°C, greater than or equal to about 180°C, or greater than or equal to about 190°C). It is required that the performance of the optoelectronic device (e.g., an organic optoelectronic device) does not deteriorate during these heat treatments. The performance degradation of the organic optoelectronic device during MLA heat treatment may not be due to the chemical decomposition of the organic material, but rather to morphological changes. When a material begins to thermally vibrate due to heat treatment, morphological changes are usually caused; however, materials with robust molecular structures may not exhibit thermal vibrations and are thus restricted and / or prevented from deteriorating due to heat treatment. The compound can be protected from molecular thermal vibrations during MLA heat treatment due to the conjugated structure in the donor portion, and therefore can be stably maintained, ensuring process stability.

[0769] In the following description, with reference to the accompanying drawings, optoelectronic devices comprising compounds according to some exemplary embodiments are described.

[0770] Figure 1 This is a cross-sectional view of an optoelectronic device according to some exemplary embodiments.

[0771] refer to Figure 1 According to an example embodiment, the optoelectronic device 100 includes a first electrode 10, a second electrode 20, and an active layer 30 between the first electrode 10 and the second electrode 20.

[0772] One of the first electrode 10 and the second electrode 20 is an anode and the other is a cathode. At least one of the first electrode 10 and the second electrode 20 may be a light-transmitting electrode, and the light-transmitting electrode may be made of, for example, a transparent conductor such as indium tin oxide (ITO) or indium zinc oxide (IZO), or a thin single-layer or multi-layer metal layer. When one of the first electrode 10 and the second electrode 20 is a non-light-transmitting electrode, it may be made of, for example, an opaque conductor such as aluminum (Al).

[0773] The active layer 30 includes p-type and n-type semiconductors to form a pn junction, and absorbs external light to generate excitons, which are then separated into holes and electrons.

[0774] The active layer 30 includes the composition for optoelectronic devices.

[0775] The active layer 30 may have a maximum absorption wavelength (λ) in a wavelength region greater than or equal to about 500 nm, for example greater than or equal to about 510 nm, greater than or equal to about 520 nm, greater than or equal to about 525 nm, greater than or equal to about 530 nm, or greater than or equal to about 535 nm and less than or equal to about 590 nm, for example less than or equal to about 580 nm, less than or equal to about 570 nm, or less than or equal to about 560 nm. 最大 ).

[0776] The active layer 30 can exhibit a relatively narrow half-width (FWHM) light absorption profile of about 50 nm to about 110 nm, for example, about 50 nm to about 100 nm. Therefore, the active layer 30 has high selectivity for light in the green wavelength region.

[0777] The active layer 30 can be a single layer or multiple layers. The active layer 30 can be, for example, an intrinsic layer (I layer), a p-type layer / I layer, an I layer / n-type layer, a p-type layer / I layer / n-type layer, a p-type layer / n-type layer, etc.

[0778] The intrinsic layer (I layer) may comprise a compound of Formula 1 and the n-type semiconductor compound in a ratio (volume ratio or thickness ratio) of approximately 1:100 to approximately 100:1. The compound of Formula 1 and the n-type semiconductor compound may also comprise a compound of Formula 1 and the n-type semiconductor compound in a ratio of approximately 1:50 to approximately 50:1, particularly approximately 1:10 to approximately 10:1, and more particularly approximately 1:1 within the aforementioned range. When the compound of Formula 1 and the n-type semiconductor compound have a ratio within the aforementioned range, excitons can be effectively generated, and a pn junction can be effectively formed.

[0779] The p-type layer may include a semiconductor compound of Formula 1, and the n-type layer may include an n-type semiconductor compound.

[0780] The active layer 30 may have a thickness of about 1 nm to about 500 nm, and particularly about 5 nm to about 300 nm, about 20 nm to about 250 nm, about 30 nm to about 200 nm, about 50 nm to about 150 nm, about 70 nm to about 130 nm, or about 80 nm to about 120 nm. When the active layer 30 has a thickness within the said range, the active layer can effectively absorb light, effectively separate holes from electrons, and transport them, thereby effectively improving photoelectric conversion efficiency. The desired thickness of the active layer 30 may be determined, for example, by the absorption coefficient of the active layer 30, and may be, for example, a thickness capable of absorbing at least about 70% or more, for example about 80% or more, and again for example about 90% or more of light.

[0781] In the optoelectronic device 100, excitons can be generated internally when light enters from the first electrode 10 and / or the second electrode 20, and when the active layer 30 absorbs light in a desired and / or alternatively predetermined wavelength region. The excitons are separated into holes and electrons in the active layer 30, and the separated holes are transported to the anode, which is one of the first electrode 10 and the second electrode 20, while the separated electrons are transported to the cathode, which is the other of the first electrode 10 and the second electrode 20, to allow current to flow in the optoelectronic device.

[0782] In the following text, refer to Figure 2 Describes optoelectronic devices based on some example implementations.

[0783] Figure 2 A cross-sectional view of an optoelectronic device according to another embodiment is shown.

[0784] refer to Figure 2 As in the aforementioned embodiments, the optoelectronic device 200 according to this embodiment includes a first electrode 10 and a second electrode 20 facing each other, and an active layer 30 between the first electrode 10 and the second electrode 20.

[0785] However, unlike the aforementioned embodiments, the optoelectronic device 200 according to this embodiment further includes charge-assisted layers 40 and 45 between the first electrode 10 and the active layer 30, and between the second electrode 20 and the active layer 30. The charge-assisted layers 40 and 45 can facilitate the transfer of holes and electrons separated from the active layer 30 to increase efficiency.

[0786] The charge-assisted layers 40 and 45 may be selected from at least one of the following: a hole injection layer (HIL) for promoting hole injection, a hole transport layer (HTL) for promoting hole transport, an electron blocking layer (EBL) for preventing electron transport, an electron injection layer (EIL) for promoting electron injection, an electron transport layer (ETL) for promoting electron transport, and a hole blocking layer (HBL) for preventing hole transport.

[0787] The charge-assisted layers 40 and 45 may comprise, for example, organic materials, inorganic materials, or organic / inorganic materials. The organic material may be an organic compound having hole or electron properties, and the inorganic material may be, for example, a metal oxide such as molybdenum oxide, tungsten oxide, nickel oxide, etc.

[0788] The hole transport layer (HTL) may include, for example, a selection from: poly(3,4-ethylenedioxythiophene):poly(sulfonated styrene) (PEDOT:PSS), polyarylamine (polyarylamine), poly(N-vinylcarbazole), polyaniline, polypyrrole, N,N,N',N'-tetra(4-methoxyphenyl)-benzidine (TPD), 4,4'-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl (α-NPD), m-MTDATA, 4,4',4”-tris(N-carbazolyl)-triphenylamine (TCTA), and combinations thereof, but is not limited thereto.

[0789] The electron blocking layer (EBL) may include, for example, a selection from: poly(3,4-ethylenedioxythiophene):poly(sulfonated styrene) (PEDOT:PSS), polyarylamine, poly(N-vinylcarbazole), polyaniline, polypyrrole, N,N,N',N'-tetra(4-methoxyphenyl)-benzidine (TPD), 4,4'-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl (α-NPD), m-MTDATA, 4,4',4”-tris(N-carbazolyl)-triphenylamine (TCTA), and combinations thereof, but is not limited thereto.

[0790] The electron transport layer (ETL) may include, for example, one of the following: 1,4,5,8-naphthalene-tetracarboxylic acid dianhydride (NTCDA), copper bath (BCP), LiF, Alq3, Gaq3, Inq3, Znq2, Zn(BTZ)2, BeBq2, and combinations thereof, but is not limited thereto.

[0791] The hole blocking layer (HBL) may include, for example, one of the following: 1,4,5,8-naphthalene-tetracarboxylic acid dianhydride (NTCDA), copper bath (BCP), LiF, Alq3, Gaq3, Inq3, Znq2, Zn(BTZ)2, BeBq2, and combinations thereof, but is not limited thereto.

[0792] Either of the charge-assisted layers 40 and 45 may be omitted.

[0793] The aforementioned optoelectronic devices can be applied to a variety of fields, such as solar cells, image sensors, photodetectors, photoelectric sensors, and organic light-emitting diodes (OLEDs), but are not limited thereto.

[0794] Hereinafter, examples of image sensors including the organic optoelectronic device are described with reference to the accompanying drawings. An organic CMOS image sensor is described as an example of an image sensor.

[0795] Figure 3 To illustrate a schematic top view of an organic CMOS image sensor according to an exemplary embodiment, and Figure 4 To display Figure 3 A cross-sectional view of an organic CMOS image sensor.

[0796] refer to Figure 3 and 4 An organic CMOS image sensor 300 according to some exemplary embodiments includes a semiconductor substrate 310 integrating photosensing devices 50B and 50R, a transfer transistor (not shown), a charge storage device 55, a lower insulating layer 60, a color filter layer 70, an upper insulating layer 80 (also referred to herein as an insulating layer), and an optoelectronic device 100. The optoelectronic device 100 may be an optoelectronic device according to any of the described exemplary embodiments and is on the semiconductor substrate 310 (e.g., directly or indirectly thereon).

[0797] The semiconductor substrate 310 may be a silicon substrate and integrates a photosensor 50, a transfer transistor (not shown), and a charge storage device 55. The photosensor 50 may include photosensors 50R and 50B. Photosensors 50R and 50B may be photodiodes.

[0798] Light sensing devices 50B and 50R, a transfer transistor, and / or a charge memory 55 may be integrated in each pixel, and as shown in the figure, light sensing devices 50B and 50R may be included in the blue pixel and the red pixel, respectively, and the charge memory 55 may be included in the green pixel.

[0799] Light sensing devices 50B and 50R sense light, and the information sensed by the light sensing devices can be transmitted through the transmission transistor. Charge memory 55 is electrically connected to optoelectronic device 100, and the information in charge memory 55 can be transmitted through the transmission transistor.

[0800] In the figure, the light sensing devices 50B and 50R are arranged in parallel without restriction, for example, or the blue light sensing device 50B and the red light sensing device 50R may be stacked in the vertical direction.

[0801] Metal lines (not shown) and pads (not shown) are formed on the semiconductor substrate 310. To reduce signal delay, the metal lines and pads may be made of metals with low resistivity, such as aluminum (Al), copper (Cu), silver (Ag), and alloys thereof, but are not limited thereto. Furthermore, the structure is not limited to the described one, and the metal lines and pads may be positioned below the photosensitive devices 50B and 50R.

[0802] A lower insulating layer 60 is formed on the metal lines and pads. The lower insulating layer 60 may be made of inorganic insulating materials such as silicon oxide and / or silicon nitride, or low dielectric constant (low K) materials such as SiC, SiCOH, SiCO, and SiOF. The lower insulating layer 60 has trenches that expose the charge storage device 55. These trenches may be filled with filler.

[0803] A color filter layer 70 is formed on the lower insulating layer 60 and may be located between the optoelectronic device 100 and the semiconductor substrate 310. The color filter layer 70 includes a blue filter 70B formed in the blue pixels and configured to selectively transmit blue light, and a red filter 70R formed in the red pixels and configured to selectively transmit red light. In some embodiments, cyan and yellow filters may be provided instead of the blue filter 70B and the red filter 70R. In this embodiment, a green filter is not included, but may be further included.

[0804] The color filter layer 70 can be omitted. For example, when the blue light sensor 50B and the red light sensor 50R are stacked in the vertical direction, the blue light sensor 50B and the red light sensor 50R can selectively absorb light in each wavelength region depending on their stacking depth, and the color filter layer 70 may not be provided.

[0805] An upper insulating layer 80 is formed on the color filter layer 70. The upper insulating layer 80 eliminates the steps caused by the color filter layer 70 and smooths the surface. The upper insulating layer 80 and the lower insulating layer 60 may include contact holes (not shown) that expose pads and vias 85 that expose the charge memory 55 of the green pixels.

[0806] The aforementioned optoelectronic device 100 is formed on the upper insulating layer 80 (e.g., directly or indirectly thereon). The optoelectronic device 100 includes a first electrode 10, an active layer 30, and a second electrode 20, as described above.

[0807] The first electrode 10 and the second electrode 20 may be transparent electrodes, and the active layer 30 is the same as described above. The active layer 30 selectively absorbs and / or senses light in the green wavelength region and acts as a color filter for the green pixels. Therefore, the optoelectronic device 100 can be configured to selectively sense light in the green wavelength region.

[0808] When light enters from the second electrode 20, the light in the green wavelength region can be mainly absorbed in the active layer 30 and photoelectric converted, while the light in the other wavelength regions passes through the first electrode 10 and can be sensed in the photosensitive devices 50B and 50R.

[0809] As described above, optoelectronic devices that selectively absorb light in the green wavelength region are stacked, thereby reducing the size of the image sensor and enabling miniaturized image sensors.

[0810] As described above, the compound represented by Formula 1 can be used as a p-type semiconductor compound. In the thin film state, aggregation between compounds is suppressed, and thus the wavelength-dependent light absorption characteristics can be maintained. Consequently, green wavelength selectivity can be maintained, crosstalk caused by unwanted absorption of light outside the green wavelength region can be reduced, and sensitivity can be increased.

[0811] In some example implementations, in Figure 4 Further, additional color filters may be provided on the optoelectronic device 100. The additional color filters may include a blue filter 70B and a red filter 70R, or a cyan filter and a yellow filter.

[0812] An organic CMOS image sensor with a color filter disposed on the optoelectronic device is shown. Figure 5 middle. Figure 5 A schematic cross-sectional view is shown to illustrate an organic CMOS image sensor according to some exemplary embodiments. References Figure 5 The organic CMOS image sensor 400 has the same characteristics as... Figure 4 The same structure exists, except that a color filter layer 72, including a blue filter 72B and a red filter 72R, is disposed on the optoelectronic device 100, such that the optoelectronic device 100 is located between the color filter layer 72 and the semiconductor substrate 310. Instead of the blue filter 72B and the red filter 72R, a cyan filter and a yellow filter may be disposed respectively.

[0813] exist Figure 4 and 5 Including Figure 1 The optoelectronic device 100 is not limited to this, and therefore can be applied in the same manner. Figure 2 200 optoelectronic devices. Figure 6 A cross-sectional view of the organic CMOS image sensor 500 to which the optoelectronic device 200 is applied.

[0814] Figure 7 This is a schematic diagram illustrating an organic CMOS image sensor according to some exemplary embodiments.

[0815] refer to Figure 7 ,picture Figure 5 As in the example implementation shown, the organic CMOS image sensor 600 includes: a semiconductor substrate 310 integrating photosensitive devices 50B and 50R, a transport transistor (not shown), a charge memory 55, an insulating layer 80, and an optoelectronic device 100.

[0816] However, unlike including Figure 5 Some exemplary embodiments of the illustrated implementations show that the organic CMOS image sensor 600 includes a blue light sensor 50B and a red light sensor 50R and does not include a color filter layer 70. The blue light sensor 50B and the red light sensor 50R are stacked vertically in a semiconductor substrate 310 (e.g., perpendicular to the direction extending from the upper surface of the semiconductor substrate 310, such as...). Figure 7 (As shown in the diagram). For example, each of the multiple red light sensing devices 50R integrated in the semiconductor substrate 310 may be stacked vertically in the semiconductor substrate 310 with each of the multiple individual blue light sensing devices 50B. The blue light sensing devices 50B and the red light sensing devices 50R are electrically connected to a charge memory 55, and information from the charge memory 55 may be transmitted via the transfer transistor (not shown). The blue light sensing devices 50B and the red light sensing devices 50R may selectively absorb light in different wavelength regions depending on the stacking depth.

[0817] As described above, photoelectric devices that selectively absorb light in the green wavelength region are stacked, and the red light sensing device and the blue light sensing device are stacked, thereby reducing the size of the image sensor and enabling a miniaturized image sensor. As described above, the photoelectric device 100 has improved green wavelength selectivity, and while increasing sensitivity, crosstalk caused by unnecessary absorption of light in wavelength regions other than green is reduced.

[0818] exist Figure 7 Including Figure 1 The optoelectronic device 100 is not limited to this, and therefore can be applied in the same manner. Figure 2 200 optoelectronic devices.

[0819] Figure 8 This is a schematic diagram illustrating an organic CMOS image sensor according to another embodiment.

[0820] refer to Figure 8The organic CMOS image sensor according to this embodiment includes stacked green photoelectric devices G that selectively absorb light in the green wavelength region, blue photoelectric devices B that selectively absorb light in the blue wavelength region, and red photoelectric devices R that selectively absorb light in the red wavelength region. To reiterate, the organic CMOS image sensor may include green photoelectric devices configured to selectively sense light in the green wavelength region, blue photoelectric devices configured to selectively sense light in the blue wavelength region, and red photoelectric devices configured to selectively sense light in the red wavelength region, wherein the green, blue, and red photoelectric devices are stacked, such as at least... Figure 8 As shown in the image.

[0821] In the figure, the green optoelectronic device, the blue optoelectronic device, and the red optoelectronic device are stacked sequentially, but the stacking order can be changed without restriction.

[0822] The green optoelectronic device G may be the aforementioned optoelectronic device 100 or optoelectronic device 200, the blue optoelectronic device B may include electrodes facing each other and an active layer of organic material therebetween that selectively absorbs light in the blue wavelength region, and the red optoelectronic device R may include electrodes facing each other and an active layer of organic material therebetween that selectively absorbs light in the red wavelength region.

[0823] As described above, a green optoelectronic device G that selectively absorbs light in the green wavelength region, a blue optoelectronic device B that selectively absorbs light in the blue wavelength region, and a red optoelectronic device R that selectively absorbs light in the red wavelength region are stacked, thereby reducing the size of the image sensor and enabling a miniaturized image sensor.

[0824] The image sensor absorbs light in the appropriate wavelength region and can exhibit fully improved sensitivity (YSNR10) and color reproducibility (ΔE*ab), despite being a stacked structure.

[0825] Here, YSNR10 represents the sensitivity of an image sensor as measured by the method described in Juha Alakarhu's "Image Sensors and Image Quality in Mobile Phones" published in the 2007 International Image Sensor Workshop (Ogunquit Maine, USA), but expressed in lux as the minimum illumination at a signal-to-noise ratio of 10. Therefore, the smaller the YSNR10, the higher the sensitivity.

[0826] On the other hand, color reproducibility (ΔE*ab) shows the difference from the standard color in the X-Rite diagram, and ΔE*ab is defined as the distance between two points in the L*a*b* color space established by the CIE (Commission International de L'Eclairage) in 1976. For example, the color difference can be calculated according to Equation 1.

[0827] [Equation 1]

[0828]

[0829] In Equation 1,

[0830] ΔL* represents the change in chromaticity coordinate L* compared to the chromaticity coordinate L* at room temperature (approximately 20°C to approximately 25°C).

[0831] Δa* represents the change in chromaticity coordinate a* compared to its value at room temperature (approximately 20°C to 25°C), and...

[0832] Δb* represents the change in chromatic coordinate b* compared to the chromatic coordinate b* at room temperature (approximately 20°C to approximately 25°C).

[0833] To manufacture an image sensor with high sensitivity and high color reproducibility, YSNR10≤100 lux is required at ΔE*ab≤3. In this document, the compound is described as achieving a sensitivity of YSNR10≤100 lux and color reproducibility at ΔE*ab≤3.

[0834] The image sensor can be applied to a variety of electronic devices, such as mobile phones and digital cameras, but is not limited to these.

[0835] Figure 9 A block diagram of a digital camera including an image sensor according to some example embodiments.

[0836] refer to Figure 9 The digital camera 1000 includes a lens 1010, an image sensor 1020, a motor 1030, and an engine 1040. The image sensor 1020 can be used according to this application. Figure 3-8 One of the image sensors shown in the embodiment.

[0837] Lens 1010 focuses incident light onto image sensor 1020. Image sensor 1020 generates RGB data for the light received through lens 1010.

[0838] In some implementations, the image sensor 1020 may interact (connect, communicate, interface) with the engine 1040.

[0839] The motor 1030 can adjust the focal length of the lens 1010 or execute the shutter in response to control signals received from the engine 1040. The engine 1040 can control the image sensor 1020 and the motor 1030.

[0840] Engine 1040 can be connected to host / application 1050.

[0841] Figure 10 This is a schematic diagram illustrating an electronic device according to some example implementations.

[0842] refer to Figure 10 The electronic device 1100 may include a processor 1120, a memory 1130, and an image sensor 1140 that are electrically connected (coupled) together via a bus 1110.

[0843] Image sensor 1140 may be an image sensor according to one of the foregoing embodiments. Memory 1130 may be a non-transitory computer-readable medium and may store instruction programs. Memory 1130 may be non-volatile memory such as flash memory, phase-change random access memory (PRAM), magnetoresistive RAM (MRAM), resistive RAM (ReRAM), or ferroelectric RAM (FRAM), or volatile memory such as static RAM (SRAM), dynamic RAM (DRAM), or synchronous DRAM (SDRAM). Processor 1120 may execute the stored instruction programs to perform one or more functions. For example, processor 1120 may be configured to process electrical signals generated by image sensor 1140. Processor 1120 may include processing circuitry systems such as hardware including logic circuitry; hardware / software combinations such as a processor executing software; or combinations thereof. For example, the processing circuitry systems may more particularly include, but are not limited to, central processing units (CPUs), arithmetic logic units (ALUs), digital signal processors, microcomputers, field-programmable gate arrays (FPGAs), system-on-a-chip (SoCs), programmable logic units, microprocessors, application-specific integrated circuits (ASICs), etc. The processor 1120 can be configured to generate output (e.g., an image to be displayed on a display interface) based on such processing.

[0844] One or more of the processor 1120, memory 1130, motor 1030, engine 1040, or host / application 1050 may be included in, include, and / or implemented as: a processing circuit system, such as hardware including logic circuitry, a hardware / software combination, such as a processor executing software, or a combination thereof. In some exemplary embodiments, one or more of the processing circuit systems may include, but are not limited to, a central processing unit (CPU), application processor (AP), arithmetic logic unit (ALU), graphics processing unit (GPU), digital signal processor, microcomputer, field-programmable gate array (FPGA), system-on-a-chip (SoC), programmable logic unit, microprocessor, or application-specific integrated circuit (ASIC), etc. In some example implementations, any of the memory, memory cells, etc., as described herein may include a non-transitory computer-readable storage device such as a solid-state drive (SSD) that stores instruction programs, and one or more of the processing circuitry systems may be configured to execute the instruction programs to perform any or all of the functions of the processor 1120, memory 1130, motor 1030, engine 1040, or host / application 1050, etc., according to any example implementation described herein.

[0845] The embodiments are described in more detail below with reference to examples. However, these embodiments are not limiting, and the inventive concept is not limited thereto.

[0846] Synthesis Example 1: Synthesis of compounds represented by chemical formula 1-1

[0847] [Chemical Formula 1-1]

[0848]

[0849] [Reaction Scheme 1-1]

[0850]

[0851] (i) Synthesis of compound 1-1A

[0852] 2.10 g (5.16 mmol) of (4-bromo-5-iodoselenophen-2-yl)trimethylsilane and 0.900 g (4.30 mmol) of 9,9-dimethyl-9,10-dihydroacridine were placed in a microwave-safe vial and dissolved in 12 mL of toluene. 0.247 g (0.43 mmol) of bis(dibenzylacetone)palladium (Pd(dba)2), 0.34 mL (0.86 mmol) of 50 wt% triphenylphosphine (PPh3) solution, and 1.24 g (12.9 mmol) of sodium tert-butoxide (NaOtBu) were added, and the mixture was reacted in a microwave reactor at 100 °C for 30 min. The product was then filtered through diatomaceous earth, and the filtrate was concentrated and purified by silica gel column chromatography (hexane:dichloromethane = 19:1, v / v). This yielded 1.2 g of compound 1-1A (yield: 57%). Repeat the above process to obtain a sufficient amount of compound 1-1A.

[0853] (ii) Synthesis of compound 1-1B

[0854] 7.60 g (15.5 mmol) of compound 1-1A was dissolved in 150 mL of dehydrated diethyl ether. At -70 °C, 7.45 mL (18.6 mmol) of a 2.5 M n-butyllithium (n-BuLi) hexane solution (n-butyllithium solution in hexane) was slowly added and the mixture was stirred for 1 hour. At -70 °C, 1.71 mL (23.3 mmol) of dehydrated acetone was added, and the mixture was stirred at room temperature for 1 hour. The product was washed with an aqueous sodium chloride solution, extracted with ethyl acetate, and dried by adding anhydrous magnesium sulfate. The obtained product was separated and purified by silica gel column chromatography (hexane:dichloromethane = 2:3 v / v) to obtain 4.00 g of compound 1-1B (yield: 55%). The above process was repeated to obtain a sufficient amount of compound 1-1B.

[0855] (iii) Synthesis of compound 1-1C

[0856] 5.43 g (12.1 mmol) of compound 1-1B was dissolved in 120 mL of tetrahydrofuran. 13.3 mL (13.3 mmol) of tetrabutylammonium fluoride (TBAF) was added dropwise, followed by stirring for 1 hour. After washing the reaction mixture with an aqueous sodium chloride solution, anhydrous magnesium sulfate was added to the organic layer to dry it, and then the organic layer was concentrated. The obtained product was separated and purified by silica gel column chromatography (hexane:dichloromethane = 9:1 v / v) to obtain 4.2 g of compound 1-1C (yield: 92%).

[0857] (iv) Synthesis of compound 1-1D

[0858] 2.16 g (5.71 mmol) of compound 1-1C was dissolved in 250 mL of toluene. 3.71 mL (57.1 mmol) of methanesulfonic acid was added dropwise, and the mixture was stirred for 12 hours. The product was poured into ice water and neutralized by adding 2 M sodium hydroxide aqueous solution. The organic layer extracted with toluene was then washed with sodium chloride aqueous solution. Anhydrous magnesium sulfate was added to the organic layer to dry it, and then the organic layer was concentrated. The obtained product was purified by silica gel column chromatography (hexane:dichloromethane = 9:1 v / v) to obtain 1.4 g of compound 1-1D (yield: 63%).

[0859] (v) Synthesis of compound 1-1E

[0860] 0.74 mL (7.9 mmol) of phosphoryl chloride was added dropwise to 2.00 mL (25.7 mmol) of N,N-dimethylformamide at 0 °C, followed by stirring at room temperature for 2 hours. This solution was then slowly added at 0 °C to a solution of 1.50 g (3.96 mmol) of compound 1-1D in 50 mL of dichloromethane, followed by stirring at room temperature for 1 hour. Water was added to the obtained product, and 2 M sodium hydroxide aqueous solution was added until the pH reached 14, followed by stirring at room temperature for 2 hours. The organic layer extracted with dichloromethane was washed with an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The obtained product was separated and purified by silica gel column chromatography (the volume ratio was changed from hexane:dichloromethane = 3:2 to 100% dichloromethane) to obtain 1.42 g of compound 1-1E (yield: 88%).

[0861] (vi) Synthesis of compounds represented by chemical formula 1-1

[0862] 1.00 g (2.46 mmol) of compound 1-1E was suspended in 100 mL of ethanol, and 0.420 g (2.69 mmol) of 1,3-dimethylbarbituric acid was added. The mixture was stirred at 50 °C for 4 hours and concentrated under reduced pressure. The result was dissolved in chloroform and filtered through a silica gel filter. The filtrate was concentrated under reduced pressure, and the product was recrystallized from chloroform and ethanol to obtain 1.05 g of the compound represented by formula 1-1 (yield: 78.4%). The obtained compound was purified to a purity of 99.9% by sublimation.

[0863] 1 H-NMR (500MHz, CD2Cl2): δ 8.63 (s, 1H), 8.17 (d, 1H), 8.12 (s, 1H), 7.59 (d, 1H), 7.42-7.27 (m, 5H), 3.34 (s, 3H), 3.29 (s, 3H), 1.62 (s, 12H).

[0864] Synthesis Example 2: Synthesis of compounds represented by chemical formulas 1-2

[0865] [Chemical Formula 1-2]

[0866]

[0867] The compounds represented by chemical formulas 1-2 were obtained in the same manner as in Synthesis Example 1, except that 1H-indene-1,3(2H)-dione was used instead of 1,3-dimethylbarbituric acid in step (vi) of Synthesis Example 1. The obtained compounds were purified to a purity of 99.9% by sublimation.

[0868] 1 H-NMR (500MHz, CD2Cl2): δ8.16 (d, 1H), 8.03 (s, 1H), 8.00 (s, 1H), 7.82-7.79 (m, 2 H), 7.71-7.69(m, 2H), 7.60(d, 1H), 7.42-7.32(m, 4H), 7.27(t, 1H), 1.62(s, 12H).

[0869] Synthesis Example 3: Synthesis of compounds represented by chemical formulas 1-3

[0870] [Chemical Formulas 1-3]

[0871]

[0872] The compounds represented by chemical formulas 1-3 were obtained in the same manner as in Synthesis Example 1, except that 9H-fluorene-9-one was used instead of acetone in step (ii) of Synthesis Example 1. The obtained compounds were purified to a purity of 99.9% by sublimation.

[0873] 1 H-NMR (500MHz, CD2Cl2): δ8.38 (d, 1H), 8.28 (s, 1H), 7.85 (d, 2H), 7.67 (d, 1H), 7.46-7.40 (m, 5 H), 7.25(s, 4H), 7.22(s, 1H), 6.96(t, 1H), 6.45(d, 1H), 3.28(s, 3H), 3.27(s, 3H), 1.67(s, 6H).

[0874] Synthesis Example 4: Synthesis of compounds represented by chemical formulas 1-4

[0875] [Chemical Formulas 1-4]

[0876]

[0877] Compounds represented by chemical formulas 1-4 were obtained in the same manner as in Synthesis Example 1, except that acetone was used instead of 1,1,1-trifluoroacetone in step (ii) of Synthesis Example 1, and 1H-inden-1,3(2H)-dione was used instead of 1,3-dimethylbarbituric acid in step (vi) of Synthesis Example 1. The obtained compounds were purified to a purity of 99.9% by sublimation.

[0878] 1 H-NMR (500MHz, CD2Cl2): δ8.13 (d, 1H), 8.09 (s, 1H), 8.02 (d, 1H), 7.86-7.83 (m, 2H), 7.75- 7.73 (m, 2H), 7.61-7.50 (m, 3H), 7.36-7.31 (m, 3H), 2.11 (s, 3H), 1.95 (s, 3H), 1.26 (s, 3H).

[0879] Synthesis Reference 1: Synthesis of compounds represented by chemical formula 2-1

[0880] [Chemical Formula 2-1]

[0881]

[0882] [Reaction Scheme 2-1]

[0883]

[0884] (i) Synthesis of compound 2-1A

[0885] Compound 2-1A (2-iodoselenophene) was synthesized by referring to the method disclosed in Efficient Synthesis of 2-Iodo and 2-Dicyanomethyl Derivatives of Thiophene, Selenophene, Tellurophene, and Thieno[3,2-b]thiophene, Takahashi, K.; Tarutani, S. Heterocycles 1996, 43, 1927-1935.

[0886] (ii) Synthesis of compound 2-1B

[0887] 7.47 g (28.7 mmol) of 2-iodoselenophene and 5.00 g (23.9 mmol) of 9,9-dimethyl-9,10-dihydroacridine were dissolved in 80 mL of toluene in the presence of 5 mol% Pd(dba)2, 10 mol% tri-tert-butylphosphine (P(tBu)3), and 6.89 g (71.7 mmol) NaOtBu, and the mixture was heated under reflux for 2 hours. The obtained product was separated and purified by silica gel column chromatography (toluene:hexane = 1:4 v / v) to obtain 3.1 g of compound 2-1B (9,9-dimethyl-10-(selenophene-2-yl)-9,10-dihydroacridine) (yield: 39.5%).

[0888] (iii) Synthesis of compound 2-1C

[0889] 1.7 ml of phosphoryl chloride was added dropwise to 4.4 ml of N,N-dimethylformamide at 0 °C and stirred at room temperature (24 °C) for 1 hour. The mixture was then slowly added dropwise to 90 ml of 3.00 g of compound 2-1B dissolved in dichloromethane at 0 °C, followed by stirring at room temperature for 1 hour. 100 ml of water was added, and an aqueous sodium hydroxide solution was added until the pH reached 14, followed by stirring at room temperature for 2 hours. The organic layer extracted with dichloromethane was washed with an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated. The obtained product was separated and purified by silica gel column chromatography (the volume ratio was changed from dichloromethane:hexane = 3:2 to 100% dichloromethane) to obtain 2.90 g (yield: 89.3%) of compound 2-1C (5-(9,9-dimethylacridin-10(9H)-yl)selenophene-2-carboxaldehyde).

[0890] (iv) Synthesis of compound 2-1D

[0891] 1.00 g (2.73 mmol) of the obtained compound 2-1C was suspended in ethanol, and 0.440 g (30.1 mmol) of 1H-indene-1,3(2H)-dione was added and reacted at 50 °C for 2 h. The mixture was then filtered through a silica gel filter and the filtrate was concentrated. Subsequently, 1.05 g (yield: 77.8%) of compound 2-1D, represented by chemical formula 2-1, was obtained by recrystallization from chloroform and ethanol. The obtained compound was purified to a purity of 99.9% by sublimation.

[0892] 1 H-NMR (300MHz, CDCl3): δ7.9 (s, 1H), 7.8 (m, 5H), 7.7 (m, 2H), 7.6 (d, 2H), 7.4 (m, 4H), 7.0 (d, 1H), 1.6 (s, 6H).

[0893] Synthesis Reference 2: Synthesis of Compounds Represented by Chemical Formula 2-2

[0894] [Chemical Formula 2-2]

[0895]

[0896] The compound represented by chemical formula 2-2 was synthesized in the same manner as in synthetic reference 1, except that 1H-indene-1,3(2H)-dione in step (iv) of synthetic reference 1 was replaced with 1,3-dimethyl-2-thiobarbituric acid.

[0897] 1 H-NMR (300MHz, CDCl3): δ8.5 (s, 1H), 77.9 (d, 1H), 7.8 (d, 2H), 7.6 (d, 2H), 7.4 (m, 4H), 7.1 (d, 1H), 3.8 (d, 6H), 1.6 (s, 6H).

[0898] Synthesis Reference 3: Synthesis of Compounds Represented by Chemical Formula 2-3

[0899] [Chemical Formula 2-3]

[0900]

[0901] 2.0 g (yield: 70%) of the compound represented by chemical formula 2-3 was synthesized in the same manner as in synthesis example 2, except that diphenylamine was used instead of 9,9-dimethyl-9,10-dihydroacridine in step (i) of synthesis example 2.

[0902] 1 H-NMR (300MHz, CD2Cl2): δ7.86 (m, 6H), 7.35 (m, 4H), 7.23 (m, 6H), 4.99 (s, 1H), 4.86 (s, 1H), 1.81 (s, 3H).

[0903] Synthesis Reference 4: Synthesis of Compounds Represented by Chemical Formulas 2-4

[0904] [Chemical Formula 2-4]

[0905]

[0906] [Reaction Scheme 2-4]

[0907]

[0908] Compound 2-4B was synthesized using diphenylamine and 2,3-dibromothiophene, as described in Angewante chem., Int. Ed. Compound 2-4B 2007, 46, 1627-1629. Then, 0.74 mL of phosphoryl chloride was added dropwise to 2.3 mL of N,N-dimethylformamide at 0 °C, followed by stirring at room temperature (24 °C) for 1 hour. Accordingly, a solution of 2.1 g of compound 2-4B dissolved in 2.0 mL of dimethylformamide was slowly added dropwise at 0 °C and stirred at 80 °C for 2 hours. The result was cooled to room temperature (25 °C) and neutralized with ammonium acetate. After filtration and removal of the precipitate, the filtrate was extracted with toluene and dried over magnesium acetate, yielding an oily compound, which was then separated by silica gel column chromatography using dichloromethane to obtain compound 2-4C (1.1 g, yield: 48%).

[0909] Subsequently, 1.0 g of compound 2-4C and 0.9 g of 1H-cyclopentanop[b]naphthalene-1,3(2H)-dione were dissolved in 50 mL of ethanol, and three drops of piperidine were added. The mixture was then heated under reflux for 3 hours. After removing the solvent under reduced pressure, the residue was purified by silica gel column chromatography to obtain 1.0 g (yield: 75%) of the compound represented by formula 2-4.

[0910] Example 1: Manufacturing of Optoelectronic Devices

[0911] ITO was deposited on a glass substrate by sputtering to form an anode approximately 150 nm thick. The ITO glass substrate was then ultrasonically cleaned with acetone / isopropanol / pure water for 15 minutes each, followed by UV ozone cleaning. Subsequently, the compound according to Synthesis Example 1 and C60 were co-deposited on the ITO glass substrate at a volume ratio of 1.2:1 to form an active layer 120 nm thick. ITO was then vacuum-deposited on the active layer to a thickness of 7 nm to fabricate an optoelectronic device having an ITO (150 nm) / active layer (120 nm) / ITO (7 nm) structure.

[0912] Examples 2-4 and Reference Examples 1-4: Fabrication of Optoelectronic Devices

[0913] The optoelectronic devices according to Examples 2-4 and Reference Examples 2-4 were manufactured according to the same method as in Example 1, except that the compounds according to Examples 2-4 and Reference Examples 1-4 were used instead of the compounds of Example 1.

[0914] Evaluation 1: Light absorption properties of the compound

[0915] The evaluation depends on the wavelength of the light absorption characteristics (maximum absorption wavelength (λ) of the compounds synthesized in Examples 1-4. 最大 (), half-width (FWHM), and absorption coefficient). The compounds from Synthetic Examples 1-4 and C60 were deposited at a 1:1 volume ratio to form 100 nm thick films, and the light absorption characteristics of each film in the ultraviolet (UV)-visible (UV-Vis) region were evaluated using Cary 5000 UV spectroscopy (Varian Inc.). The results are shown in Table 1.

[0916] (Table 1)

[0917]

[0918] Referring to Table 1, the compounds of Synthetic Examples 1-4 exhibit maximum absorption wavelength, small half-width (FWHM), and high absorption coefficient in the green wavelength region. Therefore, the compounds of Synthetic Examples 1-4 exhibit excellent absorption selectivity in the green wavelength region.

[0919] Evaluation 2: Thermal stability of the compound

[0920] The thermal stability of the compounds from the synthesis examples 1-4 was evaluated by measuring their melting points (T0). m The deposition temperature was measured by thermogravimetric analysis (TGA), and the deposition characteristics were evaluated by weight reduction with increasing temperature, achieved by sublimating the compound under a high vacuum of less than or equal to 10 Pa. The results are shown in Table 2.

[0921] (Table 2)

[0922]

[0923]

[0924] *T s10 (10 wt%) (°C): Temperature at which the weight of the sample decreases by 10 wt%.

[0925] Referring to Table 2, the compounds from Synthetic Examples 1-4 exhibit adequate thermal stability.

[0926] Evaluation 3: Quantum efficiency of optoelectronic devices

[0927] The quantum efficiency of the organic optoelectronic devices according to Examples 1-4 and Reference Examples 1-4 is evaluated based on wavelength and voltage.

[0928] Quantum efficiency was measured using an IPCE measurement system (McScience Inc., Korea). First, the IPCE measurement system was calibrated using a Si photodiode (Hamamatsu Photonics KK, Japan). Then, it was mounted on the optoelectronic devices according to Examples 1-4 and Reference Examples 1-4, and their internal quantum efficiency (IQE) and external quantum efficiency (EQE) in the wavelength range of approximately 350–750 nm were measured at room temperature. Furthermore, after annealing the optoelectronic devices at 180°C and 200°C, their external quantum efficiency was measured using the aforementioned method. The results for Examples 1-3 and Reference Examples 1-4 are shown in Table 3.

[0929] (Table 3)

[0930]

[0931] Referring to Table 3, the optoelectronic devices according to Examples 1-3 exhibit excellent (internal and external) quantum efficiencies after annealing at room temperature and at a temperature greater than or equal to 180°C. Conversely, the optoelectronic device of Reference Example 3 exhibits deteriorated characteristics after annealing at 200°C, and therefore no EQE was measured. The optoelectronic devices according to Reference Examples 1, 2, and 4 exhibit deteriorated characteristics after annealing at 180°C and 200°C, and therefore no EQE was measured.

[0932] Evaluation 4: Residual charge characteristics of optoelectronic devices

[0933] When the charge from photoelectric conversion is not entirely used for signal processing but is retained in a single frame, the charge in the previous frame overlaps with the charge in the next frame and is read out. Here, the amount of charge in the next frame is referred to as the amount of residual charge. The amount of residual charge is measured by illuminating light in the 532nm green wavelength region in which photoelectric conversion can occur for a desired and / or alternatively predetermined time, turning off the light, and using an oscilloscope device at 10... -6 The current measured in seconds is integrated over time. Light at 5000 lux passes through ea / μm. 2 The amount of residual charge was evaluated. Table 4 shows the measurement results of the residual charge of the optoelectronic devices according to Examples 1-4 and Reference Examples 1-3 at room temperature. In addition, the residual charge was measured after annealing the optoelectronic devices according to Examples 1-3 and Reference Examples 1-3 at 180°C and 200°C, and the results are shown in Table 5.

[0934] (Table 4)

[0935] <![CDATA[Residual charge (room temperature, ea / μm 2 )]]> Example 1 20 Example 2 36 Example 3 32 Example 4 20 Reference ratio 1 508 Reference ratio 2 550 Reference ratio 3 54

[0936] (Table 5)

[0937]

[0938]

[0939] Referring to Tables 4 and 5, the optoelectronic devices according to Examples 1-4 exhibit low residual charge at both room temperature and high temperature. In contrast, the optoelectronic devices according to Examples 1-3 exhibit high residual charge at room temperature, and the residual charge of the optoelectronic devices according to Examples 1-3 cannot be measured at high temperature because the device characteristics of Examples 1 and 2 deteriorate at 180°C, and the device characteristics of Example 3 deteriorate at 200°C.

[0940] Evaluation 5: Dark current in optoelectronic devices

[0941] The dark current (DC) of the optoelectronic devices according to Examples 1-3 and Reference Examples 1-4 was evaluated. The dark current was measured using an IPCE measurement system (McScience Inc., Korea). After calibrating the devices with Si photodiodes (HamamatsuPhotonics KK, Japan), the optoelectronic devices according to Examples 1-3 and Reference Examples 1-4 were mounted on the devices, and their dark current in the wavelength region ranging from approximately 350 nm to 750 nm was measured.

[0942] In addition, after annealing the optoelectronic devices according to Examples 1-3 and Reference Examples 1-4 at 180°C for 3 hours, at 190°C for 3 hours, and at 200°C for 3 hours, respectively, the dark current was measured in the wavelength range of approximately 350 nm to approximately 750 nm using an IPCE measurement system.

[0943] Table 6 shows the results for Examples 1-3 and Reference Examples 1-4. Dark current is the measurement at the maximum absorption wavelength when a voltage of -3V is applied.

[0944] (Table 6)

[0945]

[0946] Referring to Table 6, the optoelectronic devices according to Examples 1-3 exhibit low dark current at high temperatures. Conversely, the device characteristics of Reference Example 3 deteriorated after annealing at 190°C or higher, and the device characteristics of Reference Examples 1, 2, and 4 deteriorated after annealing at 180°C or higher, making it impossible to measure dark current.

[0947] Evaluation 6: Mobility of Optoelectronic Devices

[0948] Charge mobility was evaluated by measuring the TDCF (time-delayed collection field) mobility. Optoelectronic devices according to Examples 1-4 and Reference Example 1 were illuminated with a 550 nm laser (pulse width: 6 nm) using a light source, and then a bias voltage (V) was applied to measure the photocurrent. The TDCF mobility was obtained using Equation 2.

[0949] [Equation 2]

[0950] Mobility = (T) 2 / (t*V)

[0951] In equation 2,

[0952] T is the thickness of the active layer, t is the time taken from the moment the laser is irradiated to the moment when the photocurrent is maximized, and V is the bias voltage.

[0953] The TDCF mobility results of the optoelectronic devices according to Examples 1-4 and Reference Example 1 are shown in Table 7.

[0954] (Table 7)

[0955] <![CDATA[TDCF mobility (cm 2 / V·sec)]]> Example 1 <![CDATA[2.6×10 -5 ]]> Example 2 <![CDATA[2.1×10 -5 ]]> Example 3 <![CDATA[1.3×10 -5 ]]> Example 4 <![CDATA[3.3×10 -5 ]]> Reference ratio 1 <![CDATA[6.8×10 -6 ]]>

[0956] Referring to Table 7, the optoelectronic devices according to Examples 1-4 exhibit improved mobility compared to the optoelectronic device according to Reference Example 1.

[0957] Although this disclosure has been described with respect to exemplary embodiments which are now considered practical, it will be understood that the invention is not limited to the disclosed embodiments. Rather, it is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

[0958] <Symbol Explanation>

[0959] 10: First electrode; 20: Second electrode

[0960] 30: Active layer; 40, 45: Charge-assisted layer

[0961] 100, 200: Optoelectronic devices

[0962] 300, 400, 500, 600: Organic CMOS image sensors

[0963] 310: Semiconductor substrate

[0964] 70B, 72B: Blue filter; 70R, 72R: Red filter

[0965] 70, 72: Color filter layer; 85: Through-hole

[0966] 60: Lower insulation layer; 80: Upper insulation layer

[0967] 50B, 50R: Photosensitive devices; 55: Charge storage device

[0968] 1000: Digital camera; 1010: Lens

[0969] 1020: Image sensor; 1030: Motor

[0970] 1040: Engine 1050: Host / Application

Claims

1. A composition for use in an optoelectronic device, said composition comprising: n-type semiconductor compounds and p-type semiconductor compounds represented by chemical formula 2A: [Chemical Formula 2A] In chemical formula 2A, Y 1 -Y 7 each independently CR k wherein R k is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, aminyl, substituted or unsubstituted C1-C10alkyl, or substituted or unsubstituted C1-C10alkoxy, X 1 -S-, -Se-, or -Te-, X 2 -SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-(CR f R g ) n1 - or -(CR) ff R gg )-, where R b R c R d R e R f and R g Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy, and R bb and R cc R dd and R ee and R ff and R gg Each pair connects to each other to provide a ring structure, and -(CR f R g ) n1 - where n1 is 1, the ring structure is a spirocyclic structure, and the spirocyclic structure is a substituted or unsubstituted C5-C30 hydrocarbon ring group, or a substituted or unsubstituted C2-C30 heterocyclic group. R 11 and R 12 Each is independently hydrogen, deuterium, halogen, cyano, or a substituted or unsubstituted C1-C20 alkyl group. Ar 3 The substituted or unsubstituted C6-C30 hydrocarbon ring group having at least one functional group selected from C=O, C=S, C=Se, and C=Te; the substituted or unsubstituted C2-C30 heterocyclic group having at least one functional group selected from C=O, C=S, C=Se, and C=Te; or a fused ring thereof; and R 1 and R 2 Each of the following is independently hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 acyl, halogen, cyano (-CN), cyano-containing group, nitro, pentafluorothioalkyl (-SF5), hydroxyl, amino, hydrazine, hydrazone, or -SiR a R b R c , where R a R b and R c Each group is independently hydrogen or a substituted or unsubstituted C1-C10 alkyl group, and the cyano group is a C1-C30 alkyl, C2-C30 alkenyl, or C2-C30 alkynyl group in which at least one hydrogen atom is replaced by a cyano group. The term "substituted" refers to the fact that the hydrogen in the functional group is replaced by the following: halogen, hydroxyl, nitro, cyano, azide, amidine, amino, hydrazine, hydrazone, carbamoyl, thiol, C1-C20 alkyl, C1-C20 alkoxy, C2-C20 alkenyl, or C2-C20 alkynyl, and The term "amino" refers to -NR'R'', where R' and R'' are each independently a hydrogen atom or a C1-C20 alkyl group.

2. The composition of claim 1, wherein... Y 4 R in k It is a halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl, or Y 7 R in k It is a halogen, cyano, C1-C10 haloalkyl, or C1-C10 cyanoalkyl, and X 2 -SiR b R c -、-GeR d R e - or -(CR) f R g ) n1 -, where R b R c R d R e R f and R g Each is independently a halogen, a C1-C20 haloalkyl, or a C1-C20 cyanoalkyl, and -(CR f R g ) n1 - n1 is 1.

3. The composition of claim 1, wherein the spirocyclic structure comprises a portion represented by chemical formula 3: [Chemical Formula 3] in, In chemical formula 3, L a -(CR) f R g ) n1 -, where R f and R g Each is independently hydrogen, halogen, cyano, unsubstituted C1-C20 alkyl, or unsubstituted C1-C20 alkoxy, and -(CR f R g ) n1 - where n1 is 1 or 2, and The hydrogen atoms of each ring are optionally replaced by at least one substituent selected from the following: halogen, unsubstituted C1-C20 alkyl, and unsubstituted C1-C20 alkoxy.

4. The composition of claim 3, wherein in formula 3, the hydrogen atoms of each ring are replaced by at least one substituent selected from the group consisting of halogens, unsubstituted C1-C20 alkyl groups, and unsubstituted C1-C20 alkoxy groups.

5. The composition of claim 1, wherein Ar 3 For cyclic groups represented by chemical formula 4: [Chemical Formula 4] in, In chemical formula 4, Ar 3 'Substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl,' Z 1 For O, S, Se or Te, and Z 2 For O, S, Se or Te, The term "alternative" is as defined in claim 1.

6. The composition of claim 1, wherein in chemical formula 2A, Ar 3 A cyclic group represented by one of chemical formulas 5A to 5G: [Chemical Formula 5A] in, In chemical formula 5A, Z 1 For O, S, Se or Te, Z 2 For O, S, Se or Te, Z 3 For N or CR c , where R c It is hydrogen or an unsubstituted C1-C10 alkyl group. R 11 R 12 R 13 R 14 and R 15 Each can be independently hydrogen, unsubstituted C1-C20 alkyl, halogen, or cyano (-CN). n is 0 or 1, and * indicates a connection point. [Chemical Formula 5B] In chemical formula 5B, Z 1 For O, S, Se or Te, Z 2 For O, S, Se or Te, Z 3 For O, S, Se or Te, R 11 and R 12 Each is independently hydrogen, an unsubstituted C1-C20 alkyl group, an unsubstituted C1-C20 alkoxy group, a halogen, or a cyano (-CN), and * indicates a connection point. [Chemical formula 5C] In the chemical formula 5C, Z 1 For O, S, Se or Te, Z 2 For O, S, Se or Te, R 11 R 12 and R 13 Each is independently hydrogen, an unsubstituted C1-C20 alkyl group, an unsubstituted C1-C20 alkoxy group, a halogen, or a cyano (-CN), and * indicates a connection point. [Chemical Formula 5D] In the chemical formula 5D, Z 1 For O, S, Se or Te, Z 2 For O, S, Se or Te, Z 3 For N or CR c , where R c It is hydrogen or an unsubstituted C1-C10 alkyl group. G 1 For O, S, Se, Te, SiR x R y or GeR z R w , where R x R y R z and R w Each is independently hydrogen, halogen, or unsubstituted C1-C20 alkyl. R 11 R 12 and R 13 Each of these can be independently hydrogen, an unsubstituted C1-C20 alkyl group, an unsubstituted C1-C20 alkoxy group, a halogen, or a cyano group. n is 0 or 1, and * indicates a connection point. [Chemical formula 5E] In the chemical formula 5E, Z 1 For O, S, Se or Te, Z 2 For O, S, Se or Te, Z 3 For N or CR c , where R c It is hydrogen or an unsubstituted C1-C10 alkyl group. G 2 For O, S, Se, Te, SiR x R y or GeR z R w , where R x R y R z and R w Each is independently hydrogen, halogen, or unsubstituted C1-C20 alkyl. R 11 R 12 and R 13 Each is independently hydrogen, an unsubstituted C1-C20 alkyl group, an unsubstituted C1-C20 alkoxy group, a halogen, or a cyano group, and * indicates a connection point. [Chemical formula 5F] In the chemical formula 5F, Z 1 For O, S, Se or Te, Z 2 For O, S, Se or Te, R 11 It is hydrogen, unsubstituted C1-C20 alkyl, halogen, or cyano (-CN), and G 3 For O, S, Se, Te, SiR x R y or GeR z R w , where R x R y R z and R w Each is independently hydrogen, halogen, or unsubstituted C1-C20 alkyl. [Chemical Formula 5G] In chemical formula 5G, Z 1 For O, S, Se or Te, R a and R b Independently hydrogen, unsubstituted C1-C10 alkyl, or cyano, Z 2 For O, S, Se or Te, and Z 3 and Z 4 Each is independently O, S, Se, Te, or CR c R d , where R c and R d Each is independently hydrogen, unsubstituted C1-C10 alkyl, or cyano, provided that Z is... 2 For CR c R d At that time, R c and R d At least one of them is a cyano group.

7. The composition of claim 1, wherein the compound represented by chemical formula 2A is one of the compounds in group 1: [Group 1] In group 1, Ar 3 R 1 R 2 R 11 and R 12 Same as in chemical formula 2A, and The hydrogen atoms of each aromatic ring are optionally replaced by at least one substituent selected from: deuterium, halogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and The term "alternative" is as defined in claim 1.

8. The composition of claim 1, wherein the compound represented by chemical formula 2A is one of the compounds in group 3: [Group 3] 。 9. The composition of claim 1, wherein the composition, in a thin film state, has a maximum absorption wavelength (λ) in a wavelength range greater than or equal to 500 nm and less than or equal to 600 nm. 最大 ).

10. The composition of claim 1, wherein the composition exhibits a light absorption curve with a half-width (FWHM) of 50 nm to 110 nm in the thin film state.

11. Optoelectronic devices, including The first and second electrodes facing each other, and The active layer between the first electrode and the second electrode The active layer comprises the composition as described in any one of claims 1-10.

12. An image sensor comprising the optoelectronic device as claimed in claim 11.

13. The image sensor of claim 12, further comprising: A semiconductor substrate integrating multiple first photosensitive devices configured to sense light in the blue wavelength region and multiple second photosensitive devices configured to sense light in the red wavelength region. The optoelectronic device is located on the semiconductor substrate and is configured to selectively sense light in the green wavelength region.

14. The image sensor of claim 13, further comprising: Color filter layer, The color filter layer includes a blue filter configured to selectively transmit light in the blue wavelength region and a red filter configured to selectively transmit light in the red wavelength region.

15. The image sensor of claim 13, wherein the first photosensitive device and the second photosensitive device are stacked in the semiconductor substrate in a vertical direction.

16. The image sensor of claim 12, comprising: A green optoelectronic device configured to selectively sense light in the green wavelength region, a blue optoelectronic device configured to selectively sense light in the blue wavelength region, and a red optoelectronic device configured to selectively sense light in the red wavelength region. The green, blue, and red optoelectronic devices are stacked, and The green optoelectronic device is the optoelectronic device as described in claim 11.

17. An electronic device comprising an image sensor as claimed in any one of claims 12-16.

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