Compound and optoelectronic device, image sensor and electronic device comprising the same

Abstract

Disclosed are a compound and an organic optoelectronic device, an image sensor, and an electronic device including the same, wherein the compound has a chemical formula 1. In the chemical formula 1, the definitions of each group and parameter are as described in the detailed description. [Chemical formula 1].

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0125543 filed on October 10, 2019, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Example embodiments provide compounds, and optoelectronic devices, image sensors, and electronic devices including the same. Background Art

[0004] Photoelectric devices use the photoelectric effect to convert light into electrical signals. Photoelectric devices may include photodiodes, phototransistors, etc., and may be applied to image sensors, organic light emitting diodes, etc.

[0005] Image sensors including photodiodes are becoming increasingly higher in resolution, and therefore, pixel sizes are becoming smaller. Currently, silicon photodiodes are widely used, but they have a problem of deteriorated sensitivity because they have a smaller absorption area due to small pixels. Therefore, materials that can replace silicon have been studied.

[0006] The organic material has a high absorption coefficient and selectively absorbs light in a specific wavelength region depending on the molecular structure, and thus can replace both the photodiode and the color filter, and as a result, improve sensitivity and contribute to high integration. Summary of the invention

[0007] Example embodiments provide a compound capable of selectively absorbing light in a green wavelength region and having improved thermal stability.

[0008] Example embodiments also provide optoelectronic devices (eg, organic optoelectronic devices) that can selectively absorb light in a green wavelength region and maintain good efficiency even under high temperature conditions.

[0009] Example embodiments also provide an image sensor including the optoelectronic device (eg, an organic optoelectronic device).

[0010] Example embodiments also provide an electronic device including the image sensor.

[0011] According to example embodiments, the compound is represented by Chemical Formula 1.

[0012] [Chemical formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] Ar 1 is a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a condensed ring thereof,

[0016] X is O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0017] Ar 2 is 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 condensed ring group thereof,

[0018] R 1 -R 3 are 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, substituted or unsubstituted C2-C30 acyl, halogen, cyano (-CN), a cyano-containing group, nitro, pentafluorosulfanyl (-SF 5 ), hydroxyl, amine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SiR a R bR c (where R a , R b , and R c are independently hydrogen or substituted or unsubstituted C1-C10 alkyl), or a combination thereof,

[0019] R 4 is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0020] a is an integer from 0 to 4.

[0021] In some embodiments, the compound may be represented by Chemical Formula 2-1.

[0022] [Chemical formula 2-1]

[0023]

[0024] In chemical formula 2-1,

[0025] Y 1 -Y 4 N or CR independently p , where R p is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or the adjacent CR p are connected to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a condensed ring thereof,

[0026] X is O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and Rg Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0027] Ar 2 is a substituted or unsubstituted C6-C30 hydrocarbon ring group including at least one functional group selected from C=O, C=S, C=Se, and C=Te, a substituted or unsubstituted C2-C30 heterocyclic group including at least one functional group selected from C=O, C=S, C=Se, and C=Te, or a condensed ring group thereof,

[0028] R 1 -R 3 are 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, substituted or unsubstituted C2-C30 acyl, halogen, cyano (-CN), a cyano-containing group, nitro, pentafluorosulfanyl (-SF 5 ), hydroxyl, amine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SiR a R b R c (where R a , R b , and R c are independently hydrogen or substituted or unsubstituted C1-C10 alkyl), or a combination thereof,

[0029] R 4 is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0030] a is an integer from 0 to 4.

[0031] In some embodiments, the compound may be represented by Chemical Formula 2-2.

[0032] [Chemical formula 2-2]

[0033]

[0034] In chemical formula 2-2,

[0035] X is O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiRb R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0036] X 1 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0037] Ar 2 is 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 condensed ring group thereof,

[0038] R 1 -R 3 are 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, substituted or unsubstituted C2-C30 acyl, halogen, cyano (-CN), a cyano-containing group, nitro, pentafluorosulfanyl (-SF 5 ), hydroxyl, amine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SiR a R b R c (where R a , R b , and R c are independently hydrogen or substituted or unsubstituted C1-C10 alkyl), or a combination thereof,

[0039] R 4 is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy,

[0040] a is an integer from 0 to 4, and

[0041] Y 1 -Y 4 N or CR independently p , where R p is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or the adjacent CR p They are connected to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a condensed ring thereof.

[0042] In some embodiments, the compound may be represented by Chemical Formula 2-3.

[0043] [Chemical formula 2-3]

[0044]

[0045] In chemical formula 2-3,

[0046] X is O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0047] X 1 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and Re , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0048] Ar 2 is 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 condensed ring group thereof,

[0049] R 1 -R 3 are 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, substituted or unsubstituted C2-C30 acyl, halogen, cyano (-CN), a cyano-containing group, nitro, pentafluorosulfanyl (-SF 5 ), hydroxyl, amine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SiR a R b R c (where R a , R b , and R c are independently hydrogen or substituted or unsubstituted C1-C10 alkyl), or a combination thereof,

[0050] R 4 and R 5 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy,

[0051] a is an integer from 0 to 4, and

[0052] Y 1 N or CR p , where R p is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or R p and R 5 They are connected to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a condensed ring thereof.

[0053] In some embodiments, the compound may be represented by one of Chemical Formulae 2-1A to 2-1E.

[0054] [Chemical formula 2-1A]

[0055]

[0056] In Chemical Formula 2-1A,

[0057] X、Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-1,

[0058] R 11 is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0059] a1 is an integer from 0 to 4.

[0060] [Chemical formula 2-1B]

[0061]

[0062] In chemical formula 2-1B,

[0063] X、Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-1,

[0064] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy,

[0065] a1 is an integer from 0 to 4, and

[0066] a2 is an integer from 0 to 2.

[0067] [Chemical formula 2-1C]

[0068]

[0069] In Chemical Formula 2-1C,

[0070] X、Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-1,

[0071] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy,

[0072] a1 is an integer from 0 to 4, and

[0073] a2 is an integer from 0 to 2.

[0074] [Chemical formula 2-1D]

[0075]

[0076] In chemical formula 2-1D,

[0077] X、Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-1,

[0078] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0079] a1 and a2 are independently integers ranging from 0-4.

[0080] [Chemical formula 2-1E]

[0081]

[0082] In chemical formula 2-1E,

[0083] X、Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-1,

[0084] X 1 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d, R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0085] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0086] a1 and a2 are independently integers of 0-2.

[0087] In some embodiments, the compound may be represented by one of Chemical Formulae 2-2A to 2-2J.

[0088] [Chemical Formula 2-2A]

[0089]

[0090] In Chemical Formula 2-2A,

[0091] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0092] R 11 is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0093] a1 is an integer from 0 to 4.

[0094] [Chemical formula 2-2B]

[0095]

[0096] In chemical formula 2-2B,

[0097] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0098] R 11 and R 12are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy,

[0099] a1 is an integer from 0 to 4, and

[0100] a2 is an integer from 0 to 2.

[0101] [Chemical formula 2-2C]

[0102]

[0103] In chemical formula 2-2C,

[0104] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0105] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0106] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0107] a1 and a2 are independently integers of 0-2.

[0108] [Chemical formula 2-2D]

[0109]

[0110] In chemical formula 2-2D,

[0111] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0112] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0113] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0114] a1 and a2 are independently integers of 0-2.

[0115] [Chemical formula 2-2E]

[0116]

[0117] In chemical formula 2-2E,

[0118] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0119] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy,

[0120] a1 is an integer from 0 to 4, and

[0121] a2 is an integer from 0 to 2.

[0122] [Chemical formula 2-2F]

[0123]

[0124] In chemical formula 2-2F,

[0125] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0126] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from Rb and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0127] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0128] a1 and a2 are independently integers of 0-2.

[0129] [Chemical formula 2-2G]

[0130]

[0131] In chemical formula 2-2G,

[0132] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0133] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R gAt least one pair of is connected to each other to form a spiro ring structure),

[0134] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0135] a1 and a2 are independently integers of 0-2.

[0136] [Chemical formula 2-2H]

[0137]

[0138] In the chemical formula 2-2H,

[0139] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0140] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy,

[0141] a1 is an integer from 0 to 4, and

[0142] a2 is an integer from 0 to 2.

[0143] [Chemical Formula 2-2I]

[0144]

[0145] In Chemical Formula 2-2I,

[0146] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0147] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b, R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0148] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0149] a1 and a2 are independently integers of 0-2.

[0150] [Chemical formula 2-2J]

[0151]

[0152] In chemical formula 2-2J,

[0153] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0154] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R gare independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0155] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0156] a1 and a2 are independently integers of 0-2.

[0157] In some embodiments, the compound represented by Chemical Formula 2-3 may be represented by one of Chemical Formulas 2-3A to 2-3D.

[0158] [Chemical formula 2-3A]

[0159]

[0160] In Chemical Formula 2-3A,

[0161] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-3,

[0162] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R gare independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0163] R 11 is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0164] a1 is an integer from 0 to 2.

[0165] [Chemical formula 2-3B]

[0166]

[0167] In Chemical Formula 2-3B,

[0168] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-3,

[0169] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f, and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0170] R 11 is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0171] a1 is an integer from 0 to 2.

[0172] [Chemical formula 2-3C]

[0173]

[0174] In chemical formula 2-3C,

[0175] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-3,

[0176] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and Rg at least one pair of which is connected to each other to form a spiro ring structure), and

[0177] Y 2 -Y 5 N or CR independently p , where R p is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or the adjacent CR p They are connected to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a condensed ring thereof.

[0178] [Chemical formula 2-3D]

[0179]

[0180] In chemical formula 2-3D,

[0181] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-3,

[0182] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R gat least one pair of which is connected to each other to form a spiro ring structure), and

[0183] Y 2 -Y 5 N or CR independently p , where R p is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or the adjacent CR p They are connected to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a condensed ring thereof.

[0184] In some embodiments, in Chemical Formula 1, Ar 2 It may be a cyclic group represented by Chemical Formula 3.

[0185] [Chemical formula 3]

[0186]

[0187] In chemical formula 3,

[0188] Ar 2 ' is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group,

[0189] Z 1 is O, S, Se, or Te,

[0190] Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, and wherein when Z 2 CR a R b When R a and R b At least one of the groups is a cyano group or a group containing a cyano group.

[0191] In some embodiments, in Chemical Formula 1, Ar 2 It may be a cyclic group represented by one of Chemical Formulae 4A to 4F.

[0192] [Chemical Formula 4A]

[0193]

[0194] In Chemical Formula 4A,

[0195] Z1 is O, S, Se, or Te,

[0196] Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group or a group containing a cyano group,

[0197] Z 3 N or CR c (where R c is hydrogen, deuterium, or substituted or unsubstituted C1-C10 alkyl),

[0198] R 11 , R 12 , R 13 , R 14 , and R 15 are the same or different and are 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, wherein R 12 and R 13 and R 14 and R 15 exist independently or are linked to each other to form a fused aromatic ring,

[0199] n is 0 or 1, and

[0200] * is the connecting part.

[0201] [Chemical Formula 4B]

[0202]

[0203] In Chemical Formula 4B,

[0204] Z 1 is O, S, Se, or Te,

[0205] Z 2 O, S, Se, Te, or CR a R b , where R a and R bare independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group or a group containing a cyano group,

[0206] Z 3 O, S, Se, Te, or C(R a )(CN)(where R a is hydrogen, cyano (-CN), or C1-C10 alkyl),

[0207] R 11 and R 12 are 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

[0208] * is the connecting part.

[0209] [Chemical formula 4C]

[0210]

[0211] In chemical formula 4C,

[0212] Z 1 is O, S, Se, or Te,

[0213] Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group or a group containing a cyano group,

[0214] R 11 , R 12 , and R 13 are the same or different and are 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

[0215] * is the connecting part.

[0216] [Chemical Formula 4D]

[0217]

[0218] In chemical formula 4D,

[0219] Z 1 is O, S, Se, or Te,

[0220] Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group or a group containing a cyano group,

[0221] Z 3 N or CR c (where R c is hydrogen or substituted or unsubstituted C1-C10 alkyl),

[0222] G 1 O, S, Se, Te, SiR x R y , or GeR z R w , where R x , R y , R z , and R w are the same or different and are independently hydrogen, halogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl,

[0223] R 11 , R 12 , and R 13 are the same or different and are 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, a group containing a cyano, or a combination thereof, wherein R 12 and R 13 exist independently or are linked to each other to form an aromatic ring,

[0224] n is 0 or 1, and

[0225] * is the connecting part.

[0226] [Chemical formula 4E]

[0227]

[0228] In Chemical Formula 4E,

[0229] Z 1 is O, S, Se, or Te,

[0230] Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group or a group containing a cyano group,

[0231] Z 4 NR a , CR b R c ,O,S,Se,Te,S(=O),S(=O) 2 、SiR d R e and GeR f R g (where R a , R b , R c , R d , R e , R d , R e , R f and R g is hydrogen or substituted or unsubstituted C1-C10 alkyl),

[0232] G 2 O, S, Se, Te, SiR x R y , or GeR z R w , where R x , R y , R z , and R ware the same or different and are independently hydrogen, halogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl,

[0233] R 11 , R 12 , and R 13 are the same or different and are 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, a group containing a cyano, or a combination thereof,

[0234] n is 0 or 1, and

[0235] * is the connecting part.

[0236] [Chemical formula 4F]

[0237]

[0238] In Chemical Formula 4F,

[0239] Z 1 is O, S, Se, or Te,

[0240] Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group or a group containing a cyano group,

[0241] R 11 is 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

[0242] G 3 O, S, Se, Te, SiR x R y , or GeR z R w , where R x , R y , R z , and R ware the same or different and independently hydrogen, halogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl.

[0243] In some embodiments, Ar 2 may be a cyclic group represented by Chemical Formula 4A and Ar 2 It can be represented by one of the chemical formulas 4A-1, 4A-2, or 4A-3,

[0244] [Chemical Formula 4A-1]

[0245]

[0246] [Chemical Formula 4A-2]

[0247]

[0248] [Chemical Formula 4A-3]

[0249]

[0250] In Chemical Formulas 4A-1 and 4A-2,

[0251] Z 3 , R 11 ,n,R 12 , R 13 , R 14 , and R 15 Same as in Chemical Formula 4A, and

[0252] In Chemical Formula 4A-3, Z 1 , Z 2 , Z 3 , R 11 , and n are the same as in Chemical Formula 4A,

[0253] R 12a and R 12b are 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, m1 and m2 are independently integers of 0-4, and Ph 1 and Ph 2 It is a fused phenylene ring.

[0254] In some embodiments, Ar 2 may be a cyclic group represented by Chemical Formula 4B and Ar 2 It can be represented by one of the chemical formulas 4B-1, 4B-2, or 4B-3,

[0255]

[0256] In Formulas 4B-1, 4B-2, and 4B-3, R 11 and R 12 Same as in Chemical Formula 4B.

[0257] In some embodiments, Ar 2 may be a cyclic group represented by Chemical Formula 4C and Ar 2 It can be represented by one of the chemical formulas 4C-1 or 4C-2,

[0258]

[0259] In chemical formulas 4C-1 and 4C-2, R 11 -R 13 Same as in Chemical Formula 4C.

[0260] In some embodiments, the compound represented by Chemical Formula 1 may have an aspect ratio (Z / X) obtained by dividing the shortest length (Z) by the longest length (X) in the range of less than or equal to about 0.30.

[0261] In some embodiments, the compound in a thin film state may have a maximum absorption wavelength (λ) within a wavelength range of greater than or equal to about 500 nm and less than or equal to about 580 nm, for example, greater than or equal to about 520 nm and less than or equal to about 555 nm. 最大 ).

[0262] In some embodiments, the compound may exhibit a light absorption curve having a full width at half maximum (FWHM) of about 50 nm to about 100 nm.

[0263] In some embodiments, the compound may be a p-type semiconductor compound, the compound may have a HOMO energy level ranging from about -5.2 eV to about -5.8 eV and an energy band gap ranging from about -2.12 eV to about -2.48 eV, the LUMO energy level of the compound may be in the range of about -3.7 eV to about -2.7 eV, and the compound may have a molecular weight of about 300 g / mol to about 1500 g / mol.

[0264] In some embodiments, the compound may be represented by Chemical Formula 1A or Chemical Formula 1B,

[0265]

[0266]

[0267] In Chemical Formulas 1A and 1B,

[0268] Ar 1 ,Ar2 , R 1 -R 4 , and a are the same as in Chemical Formula 1, and

[0269] X' is Si, Ge, or C.

[0270] According to another embodiment, a photoelectric device (eg, an organic photoelectric device) includes first and second electrodes facing each other, and an active layer including the compound represented by Chemical Formula 1 interposed between the first and second electrodes.

[0271] According to another embodiment, an image sensor includes the optoelectronic device.

[0272] In some embodiments, the image sensor may include: a semiconductor substrate integrated with a plurality of first light sensing devices that sense light in a blue wavelength region and a plurality of second light sensing devices that sense light in a red wavelength region, and the optoelectronic device that is on the semiconductor substrate and selectively senses light in a green wavelength region.

[0273] The first light sensing device and the second light sensing device may be stacked in a vertical direction in the semiconductor substrate.

[0274] The image sensor may further include a color filter layer including a blue filter selectively transmitting light in a blue wavelength region and a red filter selectively transmitting light in a red wavelength region.

[0275] The image sensor may include a green photoelectric device, a blue photoelectric device that selectively absorbs light in a blue wavelength region, and a red photoelectric device that selectively absorbs light in a red wavelength region, which are stacked as the photoelectric device.

[0276] According to another embodiment, an electronic device includes the image sensor.

[0277] The compound can selectively absorb light in the green wavelength region and can have improved thermal stability and charge mobility. The compound improves the efficiency of the device by increasing the wavelength selectivity in the green wavelength region, and provides an optoelectronic device, an image sensor, and an electronic device that do not deteriorate performance even under a high temperature process due to improved thermal stability. BRIEF DESCRIPTION OF THE DRAWINGS

[0278] Figure 1 To show a cross-sectional view of an optoelectronic device according to one embodiment,

[0279] Figure 2 To show a cross-sectional view of an optoelectronic device according to another embodiment,

[0280] Figure 3 To show a schematic top view of an organic CMOS image sensor according to one embodiment,

[0281] Figure 4 To display Figure 3 Cross-sectional view of an organic CMOS image sensor.

[0282] Figure 5 2 is a schematic cross-sectional view showing an organic CMOS image sensor according to another embodiment.

[0283] Figure 6 2 is a schematic cross-sectional view showing an organic CMOS image sensor according to another embodiment.

[0284] Figure 7 2 is a schematic cross-sectional view showing an organic CMOS image sensor according to another embodiment.

[0285] Figure 8 2 is a schematic top view showing an organic CMOS image sensor according to another embodiment.

[0286] Fig. 9 is a block diagram of a digital camera including an image sensor according to an embodiment, and

[0287] Fig.10 is a schematic diagram of an electronic device according to an example embodiment. DETAILED DESCRIPTION

[0288] Example embodiments will be described in detail below and can be easily performed by those having ordinary skills in the relevant field. However, the present disclosure can be embodied in many different forms and should not be construed as limited to the example embodiments set forth herein.

[0289] In the accompanying drawings, the thickness of layers, films, panels, regions, etc. is exaggerated for clarity. In the specification, the same reference numerals always represent 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 the other element or there may be intermediate elements. On the contrary, when an element is referred to as being "directly on" another element, there are no intermediate elements.

[0290] In the drawings, parts that are not related to the description are omitted for clarity of the embodiments, and in the specification, the same or similar constituent elements are always denoted by the same reference numerals.

[0291] As used herein, “at least one of A, B, or C,” “one of A, B, C, or a combination thereof,” and “one of A, B, C, and a combination thereof” refer to each constituent element, and a combination thereof (for example, A; B; A and B; A and C; B and C; or A, B, and C).

[0292] As used herein, when no specific definition is otherwise provided, "substituted" refers to a compound or functional group in which a hydrogen atom is replaced by a substituent selected from the group consisting of a halogen atom (F, Br, Cl, or I), a hydroxyl group, a nitro group, a cyano group, an azido group, an amidine group, an amine group (-NR'R", wherein R' and R" are the same or different and are 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, groups, ester groups, carboxyl groups or their salts, sulfonic acid groups or their salts, phosphoric acid groups or their salts, C1-C20 alkyl groups, C1-C20 alkoxy groups, C2-C20 alkenyl groups, C2-C20 alkynyl groups, C6-C30 aryl groups, C7-C30 aralkyl groups, C2-C20 heteroaryl groups, C3-C20 heteroaralkyl groups, C3-C30 cycloalkyl groups, C3-C15 cycloalkenyl groups, C6-C15 cycloalkynyl groups, C2-C20 heterocycloalkyl groups, and combinations thereof.

[0293] As used herein, when no specific definition is provided in addition, an "aromatic hydrocarbon group" may be a hydrocarbon ring group having an aromatic hydrocarbon ring, in which all ring atoms are carbon atoms and form a conjugated structure. The aromatic hydrocarbon group may include a monocyclic, non-fused polycyclic, or fused polycyclic (e.g., a ring sharing adjacent carbon atom pairs) hydrocarbon ring group, and the other (one or more) rings of the non-fused polycyclic hydrocarbon ring group and the fused polycyclic hydrocarbon ring group may be an aromatic hydrocarbon ring or a hydrocarbon ring that is not an aromatic hydrocarbon. The aromatic hydrocarbon group may be a C6-C30 aromatic hydrocarbon group, a C6-C20 aromatic hydrocarbon group, or a C6-C10 aromatic hydrocarbon group.

[0294] As used herein, when a specific definition is not otherwise provided, a "heteroaromatic hydrocarbon group" refers to a group formed by replacing 1 to 3 carbon atoms in the aromatic hydrocarbon ring of an aromatic hydrocarbon group with a heteroatom selected from N, O, S, P and Si. The heteroaromatic hydrocarbon group may be a C3-C30 heteroaromatic hydrocarbon group, a C3-C20 heteroaromatic hydrocarbon group, or a C3-C10 heteroaromatic hydrocarbon group.

[0295] As used herein, "aryl" refers to a monovalent aromatic hydrocarbon group, and "heteroaryl" refers to a monovalent heteroaromatic hydrocarbon group.

[0296] As used herein, when no specific definition is provided, a "hydrocarbon ring group" may be a C3-C30 hydrocarbon ring group. The hydrocarbon ring group may be an aromatic hydrocarbon ring group (e.g., a C6-C30 aromatic hydrocarbon group, a C6-C20 aromatic hydrocarbon group, or a C6-C10 aromatic hydrocarbon group, such as a C6-C30 aryl, a C6-C20 aryl, or a C6-C10 aryl), an alicyclic hydrocarbon ring group (e.g., a C3-C30 cycloalkyl, a C5-C30 cycloalkyl, a C3-C20 cycloalkyl, or a C3-C10 cycloalkyl), or a condensed ring group thereof. For example, the condensed ring group refers to a condensed ring group of an aromatic hydrocarbon ring and an alicyclic hydrocarbon ring, such as a condensed ring formed by connecting at least one aromatic hydrocarbon ring, such as a C6-C30 aromatic hydrocarbon group, a C6-C20 aromatic hydrocarbon group, or a C6-C10 aromatic hydrocarbon group, to at least one alicyclic hydrocarbon ring, such as a C3-C30 cycloalkyl group, a C3-C20 cycloalkyl group, or a C3-C10 cycloalkyl group.

[0297] As used herein, when specific definition is not provided in addition, "heterocyclic group" refers to a C2-C30 heterocyclic group. The heterocyclic group refers to a hydrocarbon ring group in which at least one carbon, for example 1-3 carbons, is replaced by a heteroatom selected from N, O, S, P and Si, wherein the hydrocarbon ring group is selected from an aromatic hydrocarbon ring group (e.g., a C6-C30 aromatic hydrocarbon group, a C6-C20 aromatic hydrocarbon group, or a C6-C10 aromatic hydrocarbon group, such as a C6-C30 aryl, a C6-C20 aryl, or a C6-C10 aryl), an alicyclic hydrocarbon ring group (e.g., a C3-C30 cycloalkyl, a C3-C20 cycloalkyl, or a C3-C10 cycloalkyl), and a condensed ring group thereof. In addition, one or more carbon atoms of the heterocyclic group may be replaced by a thiocarbonyl (C=S).

[0298] As used herein, when a specific definition is not otherwise provided, "hetero" means including 1 to 3 heteroatoms selected from N, O, S, Se, Te, P, and Si.

[0299] As used herein, "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, and the like.

[0300] As used herein, "cycloalkyl" refers to a monovalent hydrocarbon cyclic group in which the ring atoms are carbon, for example, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

[0301] As used herein, when no additional definition is provided, "cyano-containing group" refers to a monovalent group such as C1-C30 (e.g., C1-C20, or C1-C10) alkyl, C2-C30 (e.g., C2-C20, or C2-C10) alkenyl, or C2-C30 (e.g., C2-C20, or C2-C10) alkynyl in which at least one hydrogen is replaced by a cyano group. The 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' is independently hydrogen or C1-C10 alkyl and p is an integer of 0-10 (or 1-10). Specific examples of the cyano-containing group may be dicyanomethyl, dicyanovinyl, cyanoethynyl, etc. As used herein, the cyano-containing group does not include such a functional group: it only includes cyano (-CN).

[0302] As used herein, when a definition is not otherwise provided, "a combination thereof" refers to at least two groups bonded to each other through a single bond or a C1-C10 alkylene group, or at least two condensed groups.

[0303] As used herein, when no definition is otherwise provided, the “aromatic hydrocarbon group” includes a C6-C30 aromatic hydrocarbon group such as a C6-C30 aryl group or a C6-C30 arylene group such as a phenyl group or a naphthyl group, but is not limited thereto.

[0304] As used herein, when no definition is otherwise provided, an "aliphatic hydrocarbon group" may include, for example, a C1-C15 alkyl group such as methyl, ethyl, propyl, etc., a C1-C15 alkylene group, a C2-C15 alkenyl group such as ethenyl or propenyl, a C2-C15 alkynyl group such as ethynyl or propynyl, but is not limited thereto.

[0305] As used herein, when a definition is not otherwise provided, “aromatic ring” refers to a C5-C12 ring group (e.g., C6-C10 aryl group) providing a conjugated structure or a C2-C10 heterocyclic group (e.g., C2-C10 heteroaryl group) providing a conjugated structure.

[0306] As used herein, when no definition is provided otherwise, a "spirocyclic structure" may be a substituted or unsubstituted C5-C30 hydrocarbon ring group or a substituted or unsubstituted C2-C30 heterocyclic group that shares one atom (e.g., Si, Ge, or C) with another ring. The C5-C30 hydrocarbon ring group may be, for example, a substituted or unsubstituted C5-C30 cycloalkyl group (e.g., a substituted or unsubstituted C3-C20 cycloalkyl group or a substituted or unsubstituted C3-C10 cycloalkyl group), and the substituted or unsubstituted C2-C30 heterocyclic group may be, for example, a substituted or unsubstituted C2-C20 heterocycloalkyl group or a substituted or unsubstituted C2-C10 heterocycloalkyl group.

[0307] Hereinafter, a compound according to an embodiment is described. The compound is represented by Chemical Formula 1.

[0308] [Chemical formula 1]

[0309]

[0310] In Chemical Formula 1,

[0311] Ar 1 is a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a condensed ring thereof,

[0312] X is O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0313] Ar 2 is 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 condensed ring group thereof,

[0314] R 1 -R 3 are 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, substituted or unsubstituted C2-C30 acyl, halogen, cyano (-CN), a cyano-containing group, nitro, pentafluorosulfanyl (-SF 5 ), hydroxyl, amine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SiR a R b R c (where R a , R b , and R c are independently hydrogen or substituted or unsubstituted C1-C10 alkyl), or a combination thereof,

[0315] R 4 is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0316] a is an integer from 0 to 4.

[0317] The compound represented by Chemical Formula 1 includes an electron donor moiety containing a ring of N, a linker containing a ring of X, and a ring of Ar 2 The electron acceptor part represented by . In Chemical Formula 1, the electron donor part has a non-conjugated structure of a ring containing N, thereby improving the light absorption property of the green light region and inducing a planar structure to improve the charge mobility of the compound.

[0318] The compound represented by Chemical Formula 1 may have an aspect ratio (Z / X) obtained by dividing the shortest length (Z) by the longest length (X) in a range of about 0.30 or less, for example, about 0.25 or less, or about 0.20 or less. Within the range, the compound may maintain excellent planarity, and thus, its charge mobility may be improved.

[0319] The compound represented by Chemical Formula 1 has a donor-linker-acceptor structure of a specific structure, whereby the absorption wavelength can be adjusted within the green wavelength range (about 500 nm to about 580 nm), its deposition temperature can be reduced, and the absorption coefficient can be increased.

[0320] In Chemical Formula 1, Ar 1 It may be a C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a condensed ring thereof.

[0321] In example embodiments, the compound represented by Chemical Formula 1 may be represented by Chemical Formula 2-1.

[0322] [Chemical formula 2-1]

[0323]

[0324] In chemical formula 2-1,

[0325] X is O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0326] Ar 2is 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 condensed ring group thereof,

[0327] R 1 -R 3 are 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, substituted or unsubstituted C2-C30 acyl, halogen, cyano (-CN), a cyano-containing group, nitro, pentafluorosulfanyl (-SF 5 ), hydroxyl, amine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SiR a R b R c (where R a , R b and R c are independently hydrogen or substituted or unsubstituted C1-C10 alkyl), or a combination thereof,

[0328] R 4 is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy,

[0329] a is an integer from 0 to 4, and

[0330] Y 1 -Y 4 N or CR independently p , where R p is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or the adjacent CR p They are connected to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a condensed ring thereof.

[0331] In example embodiments, the compound represented by Chemical Formula 1 may be represented by Chemical Formula 2-2.

[0332] [Chemical formula 2-2]

[0333]

[0334] In chemical formula 2-2,

[0335] X is O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0336] X 1 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and Rf and R g At least one pair of is connected to each other to form a spiro ring structure),

[0337] Ar 2 is 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 condensed ring group thereof,

[0338] R 1 -R 3 are 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, substituted or unsubstituted C2-C30 acyl, halogen, cyano (-CN), a cyano-containing group, nitro, pentafluorosulfanyl (-SF 5 ), hydroxyl, amine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SiR a R b R c (where R a , R b and R c are independently hydrogen or substituted or unsubstituted C1-C10 alkyl), or a combination thereof,

[0339] R 4 is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy,

[0340] a is an integer from 0 to 4, and

[0341] Y 1 -Y 4 N or CR independently p , where R p is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or the adjacent CR p They are connected to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a condensed ring thereof.

[0342] In example embodiments, the compound represented by Chemical Formula 1 may be represented by Chemical Formula 2-3.

[0343] [Chemical formula 2-3]

[0344]

[0345] In chemical formula 2-3,

[0346] Y 1 N or CR p , where R p is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or R p and R 5 are connected to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a condensed ring thereof,

[0347] X is O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0348] X 1 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , Rb , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0349] Ar 2 is 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 condensed ring group thereof,

[0350] R 1 -R 3 are 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, substituted or unsubstituted C2-C30 acyl, halogen, cyano (-CN), a cyano-containing group, nitro, pentafluorosulfanyl (-SF 5 ), hydroxyl, amine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SiR a R b R c (where R a , R b and R c are independently hydrogen or substituted or unsubstituted C1-C10 alkyl), or a combination thereof,

[0351] R 4 and R 5 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0352] a is an integer from 0 to 4.

[0353] In example embodiments, the compound represented by Chemical Formula 2-1 may be represented by one of Chemical Formulas 2-1A to 2-1E.

[0354] [Chemical formula 2-1A]

[0355]

[0356] In Chemical Formula 2-1A,

[0357] X、Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-1,

[0358] R 11 is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0359] a1 is an integer from 0 to 4.

[0360] [Chemical formula 2-1B]

[0361]

[0362] In chemical formula 2-1B,

[0363] X、Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-1,

[0364] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy,

[0365] a1 is an integer from 0 to 4, and

[0366] a2 is an integer from 0 to 2.

[0367] [Chemical formula 2-1C]

[0368]

[0369] In Chemical Formula 2-1C,

[0370] X、Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-1,

[0371] R 11and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy,

[0372] a1 is an integer from 0 to 4, and

[0373] a2 is an integer from 0 to 2.

[0374] [Chemical formula 2-1D]

[0375]

[0376] In chemical formula 2-1D,

[0377] X、Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-1,

[0378] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0379] a1 and a2 are independently integers ranging from 0-4.

[0380] [Chemical formula 2-1E]

[0381]

[0382] In chemical formula 2-1E,

[0383] X、Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-1,

[0384] X 1 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R gare independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0385] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0386] a1 and a2 are independently integers of 0-2.

[0387] The compound represented by Chemical Formula 2-2 may be represented by one of Chemical Formulas 2-2A to 2-2J.

[0388] [Chemical Formula 2-2A]

[0389]

[0390] In Chemical Formula 2-2A,

[0391] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0392] R 11 is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0393] a1 is an integer from 0 to 4.

[0394] [Chemical formula 2-2B]

[0395]

[0396] In chemical formula 2-2B,

[0397] X, X 1 ,Ar 2 , R 1 -R4 , and a are the same as in Chemical Formula 2-2,

[0398] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy,

[0399] a1 is an integer from 0 to 4, and

[0400] a2 is an integer from 0 to 2.

[0401] [Chemical formula 2-2C]

[0402]

[0403] In chemical formula 2-2C,

[0404] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0405] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0406] R11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0407] a1 and a2 are independently integers of 0-2.

[0408] [Chemical formula 2-2D]

[0409]

[0410] In chemical formula 2-2D,

[0411] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0412] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0413] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0414] a1 and a2 are independently integers of 0-2.

[0415] [Chemical formula 2-2E]

[0416]

[0417] In chemical formula 2-2E,

[0418] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0419] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy,

[0420] a1 is an integer from 0 to 4, and

[0421] a2 is an integer from 0 to 2.

[0422] [Chemical formula 2-2F]

[0423]

[0424] In chemical formula 2-2F,

[0425] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0426] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , Rc , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0427] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0428] a1 and a2 are independently integers of 0-2.

[0429] [Chemical formula 2-2G]

[0430]

[0431] In chemical formula 2-2G,

[0432] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0433] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from Rb and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0434] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0435] a1 and a2 are independently integers of 0-2.

[0436] [Chemical formula 2-2H]

[0437]

[0438] In the chemical formula 2-2H,

[0439] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0440] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy,

[0441] a1 is an integer from 0 to 4, and

[0442] a2 is an integer from 0 to 2.

[0443] [Chemical Formula 2-2I]

[0444]

[0445] In Chemical Formula 2-2I,

[0446] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0447] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeRd R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0448] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0449] a1 and a2 are independently integers of 0-2.

[0450] [Chemical formula 2-2J]

[0451]

[0452] In chemical formula 2-2J,

[0453] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-2,

[0454] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , Rc , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0455] R 11 and R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0456] a1 and a2 are independently integers of 0-2.

[0457] The compound represented by Chemical Formula 2-3 may be represented by one of Chemical Formulas 2-3A to 2-3D.

[0458] [Chemical formula 2-3A]

[0459]

[0460] In Chemical Formula 2-3A,

[0461] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-3,

[0462] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , Re , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0463] R 11 is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0464] a1 is an integer from 0 to 2.

[0465] [Chemical formula 2-3B]

[0466]

[0467] In Chemical Formula 2-3B,

[0468] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-3,

[0469] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c, R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and R f and R g At least one pair of is connected to each other to form a spiro ring structure),

[0470] R 11 is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and

[0471] a1 is an integer from 0 to 2.

[0472] [Chemical formula 2-3C]

[0473]

[0474] In chemical formula 2-3C,

[0475] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-3,

[0476] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R dand R e , and R f and R g at least one pair of which is connected to each other to form a spiro ring structure), and

[0477] Y 2 -Y 5 N or CR independently p , where R p is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or the adjacent CR p They are connected to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a condensed ring thereof.

[0478] [Chemical formula 2-3D]

[0479]

[0480] In chemical formula 2-3D,

[0481] X, X 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 2-3,

[0482] X 2 For O, S, Se, Te, S(=O), S(=O) 2 NR a 、SiR b R c ,GeR d R e , or CR f R g (where R a , R b , R c , R d , R e , R f , and R g are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b , R c , R d , R e , R f , and R g Exist independently or are selected from R b and R c , R d and R e , and Rf and R g at least one pair of which is connected to each other to form a spiro ring structure), and

[0483] Y 2 -Y 5 N or CR independently p , where R p is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amine, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or the adjacent CR p They are connected to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a condensed ring thereof.

[0484] In Formula 1, Formulas 2-1 to 2-3, Formulas 2-1A to 2-1E, Formulas 2-2A to 2-2J, and Formulas 2-3A to 2-3D, when X is SiR b R c ,GeR d R e , or CR f R g When R b and R c , R d and R e , or R f and R g may exist independently or may be connected to each other to form a spiro ring structure. In addition, in Formula 2-2, Formula 2-3, Formula 2-1E, Formulas 2-2A to 2-2J, and Formulas 2-3A to 2-3D, when X 1 SiR b R c ,GeR d R e , or CR f R g When R b and R c , R d and R e , or R f and R g Can exist independently or can be connected to each other to form a spiro ring structure. In Formula 2-2C, Formula 2-2D, Formula 2-2E, Formula 2-2F, Formula 2-2G, Formula 2-2I, Formula 2-2J, Formula 2-3A, Formula 2-3B, Formula 2-3C, and Formula 2-3D, when X 2 SiR b R c ,GeR d R e, or CR f R g When R b and R c , R d and R e , or R f and R g Can exist independently or can be connected to each other to form spirocyclic structure.Described spirocyclic structure can be substituted or unsubstituted C5-C30 hydrocarbon ring group or substituted or unsubstituted C2-C30 heterocyclic group.Described C5-C30 hydrocarbon ring group can be such as substituted or unsubstituted C5-C30 cycloalkyl (for example, substituted or unsubstituted C3-C20 cycloalkyl or substituted or unsubstituted C3-C10 cycloalkyl), and described substituted or unsubstituted C2-C30 heterocyclic group can be such as substituted or unsubstituted C2-C20 heterocycloalkyl or substituted or unsubstituted C2-C10 heterocycloalkyl.

[0485] For example, when the spirocyclic structure is a C5 cycloalkyl group or a C6 cycloalkyl group, the compound represented by Chemical Formula 1 may be represented by Chemical Formula 1A or 1B.

[0486]

[0487] In Chemical Formulas 1A and 1B,

[0488] Ar 1 ,Ar 2 , R 1 -R 4 , and a are the same as in Chemical Formula 1, and X' is Si, Ge, or C.

[0489] In Chemical Formula 1, Ar 2 It can be represented by chemical formula 3.

[0490] [Chemical formula 3]

[0491]

[0492] In chemical formula 3,

[0493] Ar 2 ' is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group,

[0494] Z 1 is O, S, Se, or Te, and

[0495] Z 2 O, S, Se, Te, or CR a R b , where R a and R bare independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, and wherein when Z 2 CR a R b When R a and R b At least one of the groups is a cyano group or a group containing a cyano group.

[0496] In Chemical Formula 1, Ar 2 It may be a cyclic group represented by one of Chemical Formulae 4A to 4F.

[0497] [Chemical Formula 4A]

[0498]

[0499] In Chemical Formula 4A,

[0500] Z 1 is O, S, Se, or Te,

[0501] Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group or a group containing a cyano group,

[0502] Z 3 N or CR c (where R c is hydrogen, deuterium, or substituted or unsubstituted C1-C10 alkyl),

[0503] R 11 , R 12 , R 13 , R 14 , and R 15 are the same or different and are 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, wherein R 12 and R 13 and R 14 and R 15 exist independently or are linked to each other to form a fused aromatic ring,

[0504] n is 0 or 1, and

[0505] * is the connecting part.

[0506] [Chemical Formula 4B]

[0507]

[0508] In Chemical Formula 4B,

[0509] Z 1 is O, S, Se, or Te,

[0510] Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group or a group containing a cyano group,

[0511] Z 3 O, S, Se, Te, or C(R a )(CN)(where R a is hydrogen, cyano (-CN), or C1-C10 alkyl),

[0512] R 11 and R 12 are 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

[0513] * is the connecting part.

[0514] [Chemical formula 4C]

[0515]

[0516] In chemical formula 4C,

[0517] Z 1 is O, S, Se, or Te,

[0518] Z 2 O, S, Se, Te, or CR a R b , where R a and Rb are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group or a group containing a cyano group,

[0519] R 11 , R 12 , and R 13 are the same or different and are 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

[0520] * is the connecting part.

[0521] [Chemical Formula 4D]

[0522]

[0523] In chemical formula 4D,

[0524] Z 1 is O, S, Se, or Te,

[0525] Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group or a group containing a cyano group,

[0526] Z 3 N or CR c (where R c is hydrogen or substituted or unsubstituted C1-C10 alkyl),

[0527] G 1 O, S, Se, Te, SiR x R y , or GeR z R w , where R x , R y , Rz , and R w are the same or different and are independently hydrogen, halogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl,

[0528] R 11 , R 12 , and R 13 are the same or different and are 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, a group containing a cyano, or a combination thereof, wherein R 12 and R 13 exist independently or are linked to each other to form an aromatic ring,

[0529] n is 0 or 1, and

[0530] * is the connecting part.

[0531] [Chemical formula 4E]

[0532]

[0533] In Chemical Formula 4E,

[0534] Z 1 is O, S, Se, or Te,

[0535] Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group or a group containing a cyano group,

[0536] Z 4 NR a , CR b R c ,O,S,Se,Te,S(=O),S(=O) 2 、SiR d R e , or GeR f R g (where R a , R b , R c , Rd , R e , R d , R e , R f , and R g are independently hydrogen or substituted or unsubstituted C1-C10 alkyl),

[0537] G 2 O, S, Se, Te, SiR x R y , or GeR z R w , where R x , R y , R z , and R w are the same or different and are independently hydrogen, halogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl,

[0538] R 11 , R 12 , and R 13 are the same or different and are 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, a group containing a cyano, or a combination thereof,

[0539] n is 0 or 1, and

[0540] * is the connecting part.

[0541] [Chemical formula 4F]

[0542]

[0543] Z 1 is O, S, Se, or Te,

[0544] Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, cyano, or a cyano-containing group, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group or a group containing a cyano group,

[0545] R 11is 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

[0546] G 3 O, S, Se, Te, SiR x R y , or GeR z R w , where R x , R y , R z , and R w are the same or different and independently hydrogen, halogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl.

[0547] The cyclic group represented by Chemical Formula 4A may be a cyclic group represented by Chemical Formula 4A-1 or 4A-2.

[0548] [Chemical Formula 4A-1]

[0549]

[0550] [Chemical Formula 4A-2]

[0551]

[0552] In Chemical Formulas 4A-1 and 4A-2,

[0553] Z 3 , R 11 ,n,R 12 , R 13 , R 14 , and R 15 Same as in Chemical Formula 4A.

[0554] The cyclic group represented by Chemical Formula 4A is 12 and R 13 and / or R 14 and R 15 When independently connected to each other to form a condensed aromatic ring, they may be a ring group represented by Chemical Formula 4A-3.

[0555] [Chemical Formula 4A-3]

[0556]

[0557] In Chemical Formula 4A-3,

[0558] Z 1 , Z 2 , Z 3 , R11 , and n are the same as in Chemical Formula 4A,

[0559] R 12a and R 12b are 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,

[0560] m1 and m2 are independently integers of 0-4,

[0561] Ph 1 and Ph 2 means a fused phenylene ring and Ph may optionally be omitted 1 and Ph 2 one.

[0562] The cyclic group represented by Chemical Formula 4B may be, for example, a cyclic group represented by Chemical Formula 4B-1, 4B-2, or 4B-3.

[0563]

[0564] In Chemical Formulas 4B-1, 4B-2, and 4B-3,

[0565] R 11 and R 12 Same as in Chemical Formula 4B.

[0566] The cyclic group represented by Chemical Formula 4C may be, for example, a cyclic group represented by Chemical Formula 4C-1 or 4C-2.

[0567]

[0568] In chemical formulas 4C-1 and 4C-2,

[0569] R 11 -R 13 Same as in Chemical Formula 4C.

[0570] In Chemical Formula 1, N of the electron donor part, X of the ring containing X, and Z present in the electron acceptor part 1 (O, S, Se, or Te) enhances intramolecular interaction at a specific wavelength and thus the absorption intensity can be improved.

[0571] Specific examples of the compound represented by Chemical Formula 1 may include a compound of Chemical Formula 5A, Chemical Formula 5B, or Chemical Formula 5C, but are not limited thereto.

[0572] [Chemical Formula 5A]

[0573]

[0574] In Chemical Formula 5A,

[0575] X is the same as in Formula 1, and

[0576] The hydrogen of each aromatic ring may be replaced by a substituent selected from the following: a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C4-C30 heteroaryl group, a halogen (F, Cl, Br, or I), a cyano group (-CN), a cyano group-containing group, and combinations thereof.

[0577] [Chemical Formula 5B]

[0578]

[0579]

[0580]

[0581]

[0582]

[0583] In Chemical Formula 5B,

[0584] X is the same as in Formula 1, and

[0585] The hydrogen of each aromatic ring may be replaced by a substituent selected from the following: a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C4-C30 heteroaryl group, a halogen (F, Cl, Br, or I), a cyano group (-CN), a cyano group-containing group, and combinations thereof.

[0586] [Chemical formula 5C]

[0587]

[0588] In chemical formula 5C,

[0589] X is the same as in Formula 1, and

[0590] The hydrogen of each aromatic ring may be replaced by a substituent selected from the following: a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C4-C30 heteroaryl group, a halogen (F, Cl, Br, or I), a cyano group (-CN), a cyano group-containing group, and combinations thereof.

[0591] In Chemical Formulae 5A, 5B, and 5C, only the ring group represented by Chemical Formula 4A is shown as the acceptor structure, but the case of any one of Chemical Formulae 4B to 4F may be shown in the same manner.

[0592] The compound may selectively absorb light in a green wavelength region and may have a maximum absorption wavelength (λ) in a wavelength region of 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 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 ).

[0593] The compound may present a light absorption curve having a half width (FWHM) of about 50nm to about 100nm, such as about 50nm to about 95nm, about 60nm to about 95nm, about 70nm to about 95nm, or about 80nm to about 95nm in a thin film state. Herein, FWHM is the width of the wavelength corresponding to half of the maximum absorption point. As used herein, when no specific definition is provided in addition, it may be defined by the absorbance measured by UV-Vis spectroscopy. When the half width (FWHM) is within the range, the selectivity in the green wavelength region may be improved. The film may be a film deposited under vacuum conditions.

[0594] The compound can be formed into a thin film by a deposition method. The deposition method can provide a uniform thin film and has a small possibility of trapping impurities in the thin film, but when the compound has a melting point lower than the temperature used for deposition, products decomposed by the compound can be deposited and thus the performance of the device can deteriorate. Therefore, the compound desirably has a melting point higher than the deposition temperature. In this regard, the compound has a melting point that is higher than the deposition temperature, for example, about 10°C or higher, about 15°C or higher, about 20°C or higher, about 25°C or higher, or about 30°C or higher, and can therefore desirably be used in a deposition process.

[0595] In more detail, due to the melting point (T m ) and decomposition temperature (T d ) is similar to the donor-acceptor type material represented by the structure of Chemical Formula 1, which can be at the melting point (T m ) is thermally decomposed at. If the temperature at which the film is formed by vacuum deposition (sublimation temperature, deposition temperature, T s ) is higher than T m, decomposition occurs more preferentially than sublimation (deposition), and thus normal devices cannot be manufactured. Since such materials cannot be used to manufacture stable image sensors, T m Should be higher than T s , and T m -T s ≥10°C is more desirable.

[0596] In addition, during the manufacture of the image sensor, after the organic optoelectronic device is manufactured, a microlens array (MLA) needs to be formed to converge light. The microlens array requires a relatively high temperature (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., organic optoelectronic device) is not deteriorated during these thermal treatments. The deterioration in the performance of the organic optoelectronic device during the thermal treatment of MLA may not be caused by the chemical decomposition of the organic material, but by its morphological change. The morphological change is usually caused when the material begins to thermally vibrate due to the thermal treatment. Materials with a rigid molecular structure may not experience thermal vibrations and may be prevented from deteriorating due to the thermal treatment. The compound may be suppressed from thermal vibrations of the molecule due to the conjugated structure in the donor portion and may therefore be stably maintained during the MLA thermal treatment and process stability may be ensured.

[0597] The compound may be a p-type semiconductor compound.

[0598] Since the compound is used as a p-type semiconductor, the compound can be appropriately used as long as it has a higher LUMO energy level than an n-type semiconductor. For example, when the compound is mixed with an n-type material such as fullerene, the compound desirably has a higher LUMO energy level than fullerene having a LUMO energy level of -4.2 eV. For a suitable HOMO-LUMO energy level of the compound, when the compound has a HOMO energy level ranging from about -5.2 eV to about -5.8 eV and an energy band gap ranging from about -2.12 eV to about -2.48 eV, the LUMO energy level of the compound is in the range of about -3.7 eV to about -2.7 eV. The HOMO level can be evaluated by irradiating the film with UV light and then measuring the amount of photoelectrons emitted therefrom depending on the energy with AC-3 (Riken Keiki Co., Ltd.), and the LUMO level can be evaluated by obtaining the energy band gap with an ultraviolet-visible spectrometer (Shimadzu Corporation) and then calculating using the energy band gap and the measured HOMO level. The compound having the HOMO level, LUMO level, and energy band gap within the range can be used as a p-type semiconductor compound that effectively absorbs light in the green wavelength region, and thus has a high external quantum efficiency (EQE), and as a result, improves the photoelectric conversion efficiency.

[0599] In example embodiments, a stably depositable compound is desirable in view of thin film formation and thus the compound has a molecular weight of about 300 g / mol to about 1500 g / mol. However, even if the compound has a molecular weight outside the range, the compound can be used as long as it is depositable. In addition, when the compound is formed using a coating process to form a thin film, the compound can be used as long as it can be dissolved in a solvent and can be coated.

[0600] Hereinafter, a photoelectric device including a compound according to an embodiment is described with reference to the accompanying drawings.

[0601] Figure 1 is a cross-sectional view showing a photovoltaic device according to one embodiment.

[0602] Reference Figure 1 , a photoelectric device 100 according to example embodiments includes a first electrode 10 and a second electrode 20 , and an active layer 30 between the first electrode 10 and the second electrode 20 .

[0603] 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 thin 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).

[0604] The active layer 30 includes a p-type semiconductor and an n-type semiconductor to form a pn junction, and absorbs external light to generate excitons, and then separates the generated excitons into holes and electrons.

[0605] The active layer 30 includes a compound represented by Chemical Formula 1. The compound may function as a p-type semiconductor compound in the active layer 30 .

[0606] The compound may selectively absorb light in a green wavelength region, and the active layer 30 including the compound may have a maximum absorption wavelength (λ) in a wavelength region of 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 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 ).

[0607] The active layer 30 may exhibit a light absorption curve having a relatively narrow full width at half maximum (FWHM) of about 50 nm to about 100 nm, for example, about 50 nm to about 95 nm. Therefore, the active layer 30 has high selectivity for light in the green wavelength region.

[0608] The active layer 30 may include the compound and C60 in a volume ratio of about 0.9:1 to about 1.1:1, for example, 1:1, and may have a volume ratio of greater than or equal to about 6.5×10 4 cm -1 , for example, greater than or equal to about 6.7×10 4 cm -1 to about 10×10 4 cm -1 , or about 6.9×10 4 cm -1 to about 10×10 4 cm -1 The absorption coefficient.

[0609] The active layer 30 may further include an n-type semiconductor compound to form a pn junction.

[0610] The n-type semiconductor compound may be subphthalocyanine or a subphthalocyanine derivative, fullerene or a fullerene derivative, thiophene or a thiophene derivative, or a combination thereof.

[0611] The fullerene may include C60, C70, C76, C78, ​​C80, C82, C84, C90, C96, C240, C540, mixtures thereof, fullerene nanotubes, etc. The fullerene derivative may refer to a compound having a substituent of these fullerenes. The fullerene derivative may include a substituent such as an alkyl group (e.g., a C1-C30 alkyl group), an aryl group (e.g., a C6-C30 aryl group), a heterocyclic group (e.g., a C3-C30 cycloalkyl group), etc. Examples of the aryl and heterocyclic groups may be a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a benzo[9,10]phenanthrene ring, a tetracene ring, a biphenyl ring, a pyrrole ring, a furan ring, a thiophene ring, an imidazole ring, azole ring, thiazole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, indolizine ring, indole ring, benzofuran ring, benzothiophene ring, isobenzofuran ring, benzimidazole ring, imidazopyridine ring, quinolizine ring, quinoline ring, phthalazine ring, naphthyridine ring, quinoxaline ring, quinoline ring Quinoxazoline ring, isoquinoline ring, carbazole ring, phenanthridine ring, acridine ring, phenanthroline ring, thianthrene ring, chromene ring, xanthene ring, phenanthroline ring Azine ring, a phenolic flavin ring, a phenothiazine ring, or a phenazine ring.

[0612] The subphthalocyanine or the subphthalocyanine derivative may be represented by Chemical Formula 6.

[0613] [Chemical formula 6]

[0614]

[0615] In Chemical Formula 6,

[0616] R 31 -R 33 are 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, a halogen-containing group, or a combination thereof,

[0617] a, b, and c are independently integers from 1 to 3, and

[0618] Z is a monovalent group.

[0619] For example, Z may be a halogen or a group containing a halogen, such as F, Cl, a group containing F, or a group containing Cl.

[0620] Halogen refers to F, Cl, Br, or I, and a group containing halogen refers to an alkyl group in which at least one hydrogen is replaced by F, Cl, Br, or I (e.g., a C1-C30 alkyl group, a C1-C20 alkyl group, or a C1-C10 alkyl group).

[0621] The thiophene derivative may be represented, for example, by Chemical Formula 7 or 8, but is not limited thereto.

[0622] [Chemical formula 7]

[0623]

[0624] [Chemical formula 8]

[0625] EWG 1 -T 1 -T 2 -T 3 -EWG 2

[0626] In chemical formulas 7 and 8,

[0627] T 1 、T 2 , and T 3 is an aromatic ring including a substituted or unsubstituted thiophene moiety,

[0628] T 1 、T 2 , and T 3 Exist independently or fused with each other,

[0629] X 3 -X 8 are 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 heterocyclic group, cyano, or a combination thereof, and

[0630] EWG 1 and EWG 2 may independently be an electron withdrawing group.

[0631] For example, in Formula 7, X 3 -X 8 At least one of may be an electron withdrawing group such as a cyano-containing group.

[0632] The active layer 30 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.

[0633] [Chemical formula 9]

[0634]

[0635] In Chemical Formula 9,

[0636] R 41 -R 43 R is 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 (heteroaromatic hydrocarbon 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 group-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 of are connected to each other to provide a fused ring,

[0637] L 1 -L 3 are independently a single bond, a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C6-C30 arylene group, a divalent group (e.g., =CR x' -(CR x R y ) p -CR y' (CN) 2 , where R x , R y , R x' , and R y' is independently hydrogen or a C1-C10 alkyl group and p is an integer of 0-10 or 1-10), a substituted or unsubstituted C3-C30 heterocyclic group, or a combination thereof,

[0638] R 51 -R 53 are independently 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, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted amine (e.g., substituted or unsubstituted C1-C30 alkylamine or substituted or unsubstituted C6-C30 arylamine), substituted or unsubstituted silyl, or a combination thereof, and

[0639] a to c are independently integers ranging from 0-4.

[0640] The second p-type semiconductor compound may be configured to selectively absorb green light, and may be included in an amount of about 500 to about 1500 parts by weight based on 100 parts by weight of the compound represented by Chemical Formula 1.

[0641] The active layer 30 may be a single layer or a multilayer. The active layer 30 may be, for example, an intrinsic layer (I layer), p-type layer / I layer, I layer / n-type layer, p-type layer / I layer / n-type layer, p-type layer / n-type layer, etc.

[0642] The intrinsic layer (I layer) may include the compound of Chemical Formula 1 and the n-type semiconductor compound in a volume ratio of about 1:100 to about 100: 1. The compound of Chemical Formula 1 and the n-type semiconductor compound may be included in a volume ratio within the range of about 1:50 to about 50:1, for example, about 1:10 to about 10:1, and for example, about 1: 1. When the compound of Chemical Formula 1 and the n-type semiconductor compound have a composition ratio within the range, excitons may be effectively generated, and a pn junction may be effectively formed.

[0643] The p-type layer may include the semiconductor compound of Chemical Formula 1, and the n-type layer may include the n-type semiconductor compound.

[0644] The active layer 30 may have a thickness of about 1 nm to about 500 nm, and for example, about 5 nm to about 300 nm. When the active layer 30 has a thickness within the range, the active layer can effectively absorb light, effectively separate holes from electrons, and deliver them, thereby effectively improving the photoelectric conversion efficiency. The desirable 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 for example, about 90% or more (for example, less than 100%) of light.

[0645] In the optoelectronic device 100, 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, excitons may be generated from the inside. The excitons are separated into holes and electrons in the active layer 30, and the separated holes are transferred to an anode as one of the first electrode 10 and the second electrode 20, and the separated electrons are transferred to a cathode as the other of the first electrode 10 and the second electrode 20 to allow current to flow in the optoelectronic device.

[0646] In the following, refer to Figure 2 An optoelectronic device according to another embodiment is described.

[0647] Figure 2is a cross-sectional view showing a photovoltaic device according to another example embodiment.

[0648] Reference Figure 2 Like the above embodiment, the photoelectric device 200 according to the present embodiment includes the first electrode 10 and the second electrode 20 facing each other, and the active layer 30 between the first electrode 10 and the second electrode 20 .

[0649] However, unlike the above embodiment, the optoelectronic device 200 according to the present embodiment further includes charge auxiliary 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 auxiliary layers 40 and 45 may facilitate the transfer of holes and electrons separated from the active layer 30 to improve efficiency.

[0650] The charge auxiliary layers 40 and 45 may be at least one selected from the following: a hole injection layer (HIL) for facilitating hole injection, a hole transport layer (HTL) for facilitating hole transport, an electron blocking layer (EBL) for preventing electron transport, an electron injection layer (EIL) for facilitating electron injection, an electron transport layer (ETL) for facilitating electron transport, and a hole blocking layer (HBL) for preventing hole transport.

[0651] The charge auxiliary layers 40 and 45 may include, for example, organic materials, inorganic materials, or organic / inorganic materials. The organic materials may be organic compounds having hole or electron properties, and the inorganic materials may be, for example, metal oxides such as molybdenum oxide, tungsten oxide, nickel oxide, etc.

[0652] The hole transport layer (HTL) may include one selected from, for example, poly(3,4-ethylenedioxythiophene):poly(styrene sulfonate) (PEDOT:PSS), polyarylamine (polyarylamine), poly(N-vinylcarbazole), polyaniline, polypyrrole, N,N,N',N'-tetrakis(4-methoxyphenyl)-benzidine (TPD), 4,4'-di[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.

[0653] The electron blocking layer (EBL) may include one selected from, for example, poly(3,4-ethylenedioxythiophene):poly(styrene sulfonate) (PEDOT:PSS), polyarylamine, poly(N-vinylcarbazole), polyaniline, polypyrrole, N,N,N',N'-tetrakis(4-methoxyphenyl)-benzidine (TPD), 4,4'-di[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.

[0654] The electron transport layer (ETL) may include one selected from, for example, 1,4,5,8-naphthalene-tetracarboxylic dianhydride (NTCDA), bathocuproine (BCP), LiF, Alq 3 , Gaq 3 、Inq 3 、Znq 2 、Zn(BTZ) 2 、BeBq 2 , and combinations thereof, but are not limited thereto.

[0655] The hole blocking layer (HBL) may include one selected from, for example, 1,4,5,8-naphthalene-tetracarboxylic dianhydride (NTCDA), bathocuproin (BCP), LiF, Alq 3 , Gaq 3 、Inq 3 、Znq 2 、Zn(BTZ) 2 、BeBq 2 , and combinations thereof, but are not limited thereto.

[0656] Either one of the charge auxiliary layers 40 and 45 may be omitted.

[0657] The optoelectronic device may be applied to various fields such as solar cells, image sensors, photodetectors, light sensors, and organic light emitting diodes (OLEDs), but is not limited thereto.

[0658] Hereinafter, examples of image sensors including the organic photoelectric device are described with reference to the accompanying drawings. As an example of an image sensor, an organic CMOS image sensor is described.

[0659] Figure 3 is a schematic top view showing an organic CMOS image sensor according to an example embodiment, and Figure 4 To display Figure 3 Cross-sectional view of an organic CMOS image sensor.

[0660] Reference Figure 3 and 4, an organic CMOS image sensor 300 according to an example embodiment includes a semiconductor substrate 310 integrated with blue and red light sensing devices 50B and 50R, a transfer transistor (not shown), and a charge storage device 55, a lower insulating layer 60, a color filter layer 70, an upper insulating layer 80, and a photoelectric device 100.

[0661] The semiconductor substrate 310 may be a silicon substrate, and is integrated with blue and red light sensing devices 50B and 50R, a transfer transistor (not shown), and a charge storage 55. The blue and red light sensing devices 50B and 50R may be photodiodes.

[0662] Blue and red light sensing devices 50B and 50R, transfer transistors, and / or charge storage devices 55 may be integrated in each pixel, and as shown in the figure, blue and red light sensing devices 50B and 50R may be included in blue pixels and red pixels, respectively, and the charge storage device 55 may be included in a green pixel.

[0663] The blue and red light sensing devices 50B and 50R sense light, and information sensed by the light sensing devices can be transmitted through the transfer transistors. The charge storage 55 is electrically connected to the optoelectronic device 100, and information of the charge storage 55 can be transmitted through the transfer transistors.

[0664] In the drawing, the blue and red light sensing devices 50B and 50R are arranged in parallel, for example, without limitation, and for example, the blue light sensing device 50B and the red light sensing device 50R may be stacked in a vertical direction.

[0665] Metal wires (not shown) and pads (not shown) are formed on the semiconductor substrate 310. In order to reduce signal delay, the metal wires 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. In addition, it is not limited to the structure, and the metal wires and pads may be placed under the blue and red light sensing devices 50B and 50R.

[0666] A lower insulating layer 60 is formed on the metal line and the pad. The lower insulating layer 60 may be made of an inorganic insulating material such as silicon oxide and / or silicon nitride, or a low dielectric constant (low-K) material such as SiC, SiCOH, SiCO, and SiOF. The lower insulating layer 60 has a trench that exposes the charge storage 55. The trench may be filled with a filler.

[0667] The color filter layer 70 is formed on the lower insulating layer 60. The color filter layer 70 includes a blue filter 70B formed in a blue pixel and selectively transmitting blue light, and a red filter 70R formed in a red pixel and selectively transmitting red light. In one embodiment, a cyan filter 70C and a yellow filter 70Y may be provided instead of the blue filter 70B and the red filter 70R. In this embodiment, a green filter is not included, but a green filter may be further included.

[0668] The color filter layer 70 may be omitted. For example, when the blue light sensing device 50B and the red light sensing device 50R are stacked in a vertical direction, the blue light sensing device 50B and the red light sensing device 50R may selectively absorb light in each wavelength region depending on their stack depth, and the color filter layer 70 may not be provided.

[0669] An upper insulating layer 80 is formed on the color filter layer 70. The upper insulating layer 80 eliminates steps caused by the color filter layer 70 and smoothes the surface. The upper insulating layer 80 and the lower insulating layer 60 may include a contact hole (not shown) exposing the pad, and a through hole 85 exposing the charge storage 55 of the green pixel.

[0670] The above-mentioned photoelectric device 100 is formed on the upper insulating layer 80. As described above, the photoelectric device 100 includes the first electrode 10, the active layer 30, and the second electrode 20.

[0671] 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 a green wavelength region and replaces a color filter of a green pixel.

[0672] When light enters from the second electrode 20 , light in the green wavelength region may be mainly absorbed in the active layer 30 and photoelectrically converted, while light in the remaining wavelength regions passes through the first electrode 10 and may be sensed in the blue and red light sensing devices 50B and 50R.

[0673] As described above, the optoelectronic devices that selectively absorb light in the green wavelength region are stacked and thereby the size of the image sensor can be reduced and a miniaturized image sensor can be realized.

[0674] As described above, when the compound represented by Chemical Formula 1 is used as a semiconductor compound, aggregation between the compounds is suppressed in a thin film state, and thus the light absorption characteristics depending on the wavelength can be maintained. Thus, green wavelength selectivity can be maintained, crosstalk caused by unnecessary absorption of light other than the green wavelength region can be reduced, and sensitivity can be improved.

[0675] In one embodiment, Figure 4In the embodiment, additional color filters may be further 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 70C and a yellow filter 70Y.

[0676] Figure 5 An organic CMOS image sensor having a color filter disposed on an optoelectronic device is shown in FIG. Figure 5 Schematic cross-sectional view showing an organic CMOS image sensor according to one embodiment. Figure 5 The organic CMOS image sensor 400 has the following features: Figure 4 Same structure: A color filter layer 72 including a blue filter 72B and a red filter 72R is provided on the optoelectronic device 100. Instead of the blue filter 72B and the red filter 72R, a cyan filter 72C and a yellow filter 72Y may be provided, respectively.

[0677] exist Figure 4 and 5 Including Figure 1 The optoelectronic device 100 is not limited thereto and can be applied in the same manner. Figure 2 An optoelectronic device 200. Figure 6 is a cross-sectional view showing an organic CMOS image sensor 500 to which the optoelectronic device 200 is applied.

[0678] Figure 7 is a schematic cross-sectional view showing an organic CMOS image sensor according to another embodiment.

[0679] Reference Figure 7 ,picture Figure 5 As in the example embodiment shown in , the organic CMOS image sensor 600 includes a semiconductor substrate 310 integrated with blue and red light sensing devices 50B and 50R, a transfer transistor (not shown), and a charge storage 55 , an insulating layer 80 , and a photoelectric device 100 .

[0680] However, unlike the above-described embodiment, the organic CMOS image sensor 600 according to the present embodiment includes a stacked blue light sensing device 50B and a red light sensing device 50R and does not include a color filter layer 70. The blue light sensing device 50B and the red light sensing device 50R are electrically connected to the charge storage 55, and information of the charge storage 55 can be transmitted through a transfer transistor (not shown). Depending on the stack depth, the blue light sensing device 50B and the red light sensing device 50R can selectively absorb light in each wavelength region.

[0681] As described above, the optoelectronic device that selectively absorbs light in the green wavelength region is stacked and the red light sensing device and the blue light sensing device are stacked, so that the size of the image sensor can be reduced and a miniaturized image sensor can be realized. As described above, the optoelectronic device 100 has improved green wavelength selectivity, and crosstalk caused by unnecessary absorption of light in wavelength regions other than green can be reduced while improving sensitivity.

[0682] exist Figure 7 Including Figure 1 The optoelectronic device 100 is not limited thereto and can be applied in the same manner. Figure 2 In other words, the organic CMOS image sensor 600 may be modified to include Figure 2 Optoelectronic devices 200 instead Figure 1 An optoelectronic device 100.

[0683] Figure 8 FIG. 1 is a schematic top plan view showing an organic CMOS image sensor according to another example embodiment.

[0684] Reference Figure 8 According to the present embodiment, the organic CMOS image sensor includes a stacked green photoelectric device (G) that selectively absorbs light in a green wavelength region, a blue photoelectric device (B) that selectively absorbs light in a blue wavelength region, and a red photoelectric device (R) that selectively absorbs light in a red wavelength region.

[0685] In the figure, the red photoelectric device, the green photoelectric device, and the blue photoelectric device are sequentially stacked, but the stacking order may be changed without limitation.

[0686] The green optoelectronic device may be the aforementioned optoelectronic device 100 or optoelectronic device 200, the blue optoelectronic device may include electrodes facing each other and an active layer therebetween including an organic material that selectively absorbs light in a blue wavelength region, and the red optoelectronic device may include electrodes facing each other and an active layer therebetween including an organic material that selectively absorbs light in a red wavelength region.

[0687] As described above, a green photoelectric device (G) that selectively absorbs light in a green wavelength region, a blue photoelectric device (B) that selectively absorbs light in a blue wavelength region, and a red photoelectric device (R) that selectively absorbs light in a red wavelength region are stacked, and thereby the size of the image sensor can be reduced and a miniaturized image sensor can be realized.

[0688] The image sensor absorbs light in a suitable wavelength region and can show both improved sensitivity (YSNR10) and color reproducibility (ΔE*ab) despite a stacked structure.

[0689] Herein, YSNR10 represents the sensitivity of an image sensor, which is measured in the manner described in "Image Sensors and Image Quality in Mobile Phones" by Juha Alakarhu, printed in the 2007 International Image Sensor Symposium (Ogunquit Maine, USA), but at the minimum illumination expressed in lux at a ratio between signal and noise of 10. Therefore, the smaller the YSNR10, the higher the sensitivity.

[0690] On the other hand, color reproducibility (ΔE*ab) shows the difference from the standard color in the X-Rite color chart, and ΔE*ab was defined as the distance between two points on the L*a*b* color space by CIE (Commission International de L'Eclairage) in 1976. For example, the color difference can be calculated according to Equation 1.

[0691] [Equation 1]

[0692]

[0693] In equation 1,

[0694] ΔL * Indicates the color coordinate L at room temperature (about 20°C - about 25°C) * Compared with the color coordinate L * changes,

[0695] Δa * Represents the color coordinate a at room temperature * Compared with color coordinate a * changes, and

[0696] Δb * Represents the color coordinate b at room temperature * Compared with color coordinate b * changes.

[0697] In order to manufacture an image sensor having high sensitivity and high color reproducibility, YSNR10≤100 lux is required when ΔE*ab≤3. Herein, the compound can achieve a sensitivity of YSNR10≤100 lux and a color reproducibility of ΔE*ab≤3.

[0698] The image sensor may be applied to various electronic devices such as mobile phones, digital cameras, etc., but is not limited thereto.

[0699] Fig. 9 is a block diagram of a digital camera including an image sensor according to an embodiment.

[0700] Reference Fig. 9 , the digital camera 1000 includes a lens 1010, an image sensor 1020, a motor 1030, and an engine 1040. The image sensor 1020 may be a Figure 3-8 One of the image sensors of the embodiment shown in .

[0701] The lens 1010 focuses incident light on the image sensor 1020. The image sensor 1020 generates RGB data for the light received through the lens 1010.

[0702] In some implementations, image sensor 1020 may interface with engine 1040 .

[0703] The motor 1030 may adjust the focus of the lens 1010 or perform a shutter in response to a control signal received from the engine 1040. The engine 1040 may control the image sensor 1020 and the motor 1030.

[0704] The engine 1040 may be connected to a host / application 1050 .

[0705] Fig.10 is a schematic diagram of an electronic device according to an example embodiment.

[0706] Reference Fig.10, the electronic device 1100 may include a processor 1120, a memory 1130, and an image sensor 1140, which are electrically connected (coupled) together via a bus 1110. The image sensor 1140 may be an image sensor according to one of the aforementioned embodiments. The memory 1130 may be a non-transitory computer-readable medium and may store an instruction program. The memory 1130 may be a non-volatile memory such as a flash memory (flash memory), a phase change random access memory (PRAM), a magnetoresistive RAM (MRAM), a resistive RAM (ReRAM), or a ferroelectric RAM (FRAM), or a volatile memory such as a static RAM (SRAM), a dynamic RAM (DRAM), or a synchronous DRAM (SDRAM). The processor 1120 may execute the stored instruction program to perform one or more functions. For example, the processor 1120 may be configured to process an electrical signal generated by the image sensor 1140. The processor 1120 may include a processing circuit system such as hardware including a logic circuit; a hardware / software combination such as a processor executing software; or a combination thereof. For example, the processing circuit system may more specifically include, but is not limited to, a central processing unit (CPU), an arithmetic logic unit (ALU), a digital signal processor, a microcomputer, a field programmable gate array (FPGA), a system on a chip (SoC), a programmable logic unit, a microprocessor, an application specific integrated circuit (ASIC), etc. The processor 1120 may be configured to generate an output (e.g., an image to be displayed on a display interface) based on such processing.

[0707] Hereinafter, the embodiments are described in more detail with reference to Examples. However, these Examples are non-limiting, and the present disclosure is not limited thereto.

[0708] Synthesis Example 1: Synthesis of the compound represented by Chemical Formula 1-1

[0709] [Chemical formula 1-1]

[0710]

[0711] [Reaction Scheme 1-1]

[0712]

[0713] (i) Synthesis of Compound 1-1A

[0714] 3.1 g (12.6 mmol) of 5-chlorotellurphene-2-carboxaldehyde and 2.6 g (15.1 mmol) of 1,3-dimethyl-2-thiodihydropyrimidine-4,6 (1H, 5H) -dione (also known as 1,3-dimethyl-2-thiobarbituric acid) were heated under reflux in 50 ml of ethanol for 6 hours. The obtained product was separated and purified by silica gel column chromatography (dichloromethane) to obtain 4.5 g (90% yield) of compound 1-1A (5- ((5-chlorotellurphen-2-yl) methylene) -1,3-dimethyl-2-thiodihydropyrimidine-4,6 (1H, 5H) -dione).

[0715] (ii) Synthesis of the compound represented by Chemical Formula 1-1

[0716] 2.2 g (5.7 mmol) of compound 1-1A and 1.9 g (11.34 mmol) of 2,3-dihydro-1H-benzo [f] isoindole were added dropwise to 200 ml of 1,4-dioxane, and 0.01 ml of triethylamine was added thereto, and then stirred at 100 ° C for 12 hours. The obtained mixture was cooled to room temperature (24 ° C) to precipitate the product, followed by filtration and purification. Chloroform was used to recrystallize to obtain 2.00 g (67.0% yield) of the compound represented by chemical formula 1-1.

[0717] 1 H-NMR (500 MHz, dichloromethane-d2): δ8.46 (s, 1H), 8.27 (d, 1H), 7.84 (m, 2H), 7.71 (s, 2H), 7.45 (m, 2H), 6.94 (d, 1H), 4.35 (s, 4H), 3.71 (s, 1H), 3.66 (s, 1H).

[0718] Synthesis Example 2: Synthesis of the compound represented by Chemical Formula 1-2

[0719] [Chemical formula 1-2]

[0720]

[0721] [Reaction Scheme 1-2]

[0722]

[0723] (i) Synthesis of Compound 1-2A

[0724] 3.3 g (13.5 mmol) of 5-chlorotellurophene-2-carboxaldehyde and 2.4 g (16.2 mmol) of 1H-indene-1,3(2H)-dione were heated under reflux in 50 ml of ethanol for 6 hours. The obtained product was separated and purified by silica gel column chromatography (dichloromethane) to obtain 4.4 g (yield = 88%) of compound 1-2A (2-((5-chlorotellurophene-2-yl)methylene)-1H-indene-1,3(2H)-dione).

[0725] (ii) Synthesis of the compound represented by Chemical Formula 1-2

[0726] 2.2 g (6.0 mmol) of compound 1-2A and 2.0 g (11.9 mmol) of 2,3-dihydro-1H-benzo [f] isoindole were added dropwise to 200 ml of 1,4-dioxane, and 0.01 ml of triethylamine was added thereto, and then stirred at 100 ° C for 12 hours. The resultant was cooled to room temperature (24 ° C) to precipitate the product, followed by filtration and purification. Chloroform was used to recrystallize to obtain 2.1 g (70.0% yield) of the compound represented by chemical formula 1-2.

[0727] 1 H-NMR (500 MHz, dichloromethane-d2): δ8.43 (s, 1H), 8.24 (d, 1H), 7.82 (m, 2H), 7.7-7.68 (m, 6H), 7.41 (m, 2H), 7.04 (d, 1H), 4.3 (s, 4H).

[0728] Synthesis Example 3: Synthesis of the compound represented by Chemical Formula 1-3

[0729] [Chemical formula 1-3]

[0730]

[0731] [Reaction Scheme 1-3]

[0732]

[0733] (i) Synthesis of Compound 1-1A

[0734] 3.1 g (12.6 mmol) of 5-chlorotellurphene-2-carboxaldehyde and 2.6 g (15.1 mmol) of 1,3-dimethyl-2-thiodihydropyrimidine-4,6 (1H, 5H) -dione were heated under reflux in 50 ml of ethanol for 6 hours. The obtained product was separated and purified by silica gel column chromatography (dichloromethane) to obtain 4.5 g (90% yield) of compound 1-1A (5-((5-chlorotellurphen-2-yl)methylene)-1,3-dimethyl-2-thiodihydropyrimidine-4,6 (1H, 5H) -dione).

[0735] (ii) Synthesis of Compound 1-3

[0736] 2.4 g (6.0 mmol) of compound 1-1A and 1.4 g (12.0 mmol) of isoindole were added dropwise to 200 ml of 1,4-dioxane, and 0.01 ml of triethylamine was added thereto, followed by stirring at 100 ° C for 12 hours. The resultant was cooled to room temperature (24 ° C) to precipitate the product, followed by filtration and purification. Chloroform was used to recrystallize to obtain 2.4 g (80.0% yield) of the compound represented by Chemical Formula 1-3.

[0737] 1 H-NMR (500 MHz, dichloromethane-d2): δ8.46 (s, 1H), 8.27 (d, 1H), 7.69 (dd, 2H), 7.45 (dd, 2H), 6.94 (d, 1H), 4.35 (s, 4H), 3.71 (s, 1H), 3.63 (s, 1H).

[0738] Synthesis Example 4: Synthesis of the compound represented by Chemical Formula 1-4

[0739] [Chemical formula 1-4]

[0740]

[0741] [Reaction Scheme 1-4]

[0742]

[0743] (i) Synthesis of Compound 1-2A

[0744] 3.3 g (13.5 mmol) of 5-chlorotellurophene-2-carboxaldehyde and 2.4 g (16.2 mmol) of 1H-indene-1,3 (2H) -dione were heated under reflux in 50 ml of ethanol for 6 hours. The obtained product was separated and purified by silica gel column chromatography (dichloromethane) to obtain 4.4 g (88% yield) of compound 1-2A (2- ((5-chlorotellurophene-2-yl) methylene) -1H-indene-1,3 (2H) -dione).

[0745] (ii) Synthesis of the compound represented by Chemical Formula 1-4

[0746] 2.2 g (6.0 mmol) of compound 1-2A and 1.4 g (11.9 mmol) of isoindole were added dropwise to 200 ml of 1,4-dioxane, and 0.01 ml of triethylamine was added thereto, and then stirred at 100 ° C for 12 hours. The resultant was cooled to room temperature (24 ° C) to precipitate the product, followed by filtration and purification. Chloroform was used to recrystallize to obtain 2.2 g (73.0% yield) of the compound represented by chemical formula 1-4.

[0747] 1 H-NMR (500 MHz, dichloromethane-d2): δ8.45 (s, 1H), 8.19 (d, 1H), 7.7-7.68 (m, 8H), 7.04 (d, 1H), 4.3 (s, 4H).

[0748] Synthesis Reference Example 1: Synthesis of the compound represented by Chemical Formula 2-1 (2-((5-(10H-phenoselenazine-10-yl)tellurophene-2-yl)methylene)-1H-indene-1,3(2H)-dione)

[0749] [Chemical formula 2-1]

[0750]

[0751] [Reaction Scheme 2-1]

[0752]

[0753] (i) Synthesis of Compound 2-1A

[0754] 10.0 g (32.7 mmol) of 2-iodotellurophene and 6.17 g (25.2 mmol) of 10H-phenoselenazine were dissolved in 100 ml of anhydrous toluene in the presence of 5 mol% of bis(dibenzylideneacetone)palladium (Pd(dba) 2 ), 5 mol% tri-tert-butylphosphine (P(tBu) 3 ), and 2.66 g (27.7 mmol) of sodium tert-butoxide (NaOtBu) were heated under reflux for 2 hours. The obtained product was separated and purified by silica gel column chromatography (volume ratio of toluene: hexane = 1:4) to obtain 4.25 g (39.8% yield) of compound 2-1A (10-(tellurophen-2-yl)-10H-phenoselenazine).

[0755] (ii) Synthesis of Compound 2-1B

[0756] 1.84 ml of phosphorus oxychloride was added dropwise to 6.0 ml of N, N-dimethylformamide at -15 ° C, and then stirred at room temperature (24 ° C) for 2 hours. The resultant was slowly added dropwise to a mixture of 200 ml of dichloromethane and 4.25 g of compound 2-1A at -15 ° C, then stirred at room temperature (24 ° C) for 30 minutes and concentrated under reduced pressure. Subsequently, 100 ml of water was added thereto, an aqueous sodium hydroxide solution was added thereto until the pH became 14, and then stirred at room temperature (24 ° C) for 2 hours. The organic layer extracted by using dichloromethane was washed with an aqueous sodium chloride solution and then dried by adding anhydrous magnesium sulfate thereto. The obtained product was separated and purified by silica gel column chromatography (hexane: ethyl acetate volume ratio = 4: 1) to obtain 2.50 g (55.2% yield) of compound 2-1B (5- (10H- phenoselenazine-10-yl) tellurphene-2-carboxaldehyde).

[0757] (iii) Synthesis of the compound represented by Chemical Formula 2-1

[0758] 1.90 g (4.21 mmol) of compound 2-1B was suspended in ethanol, 0.74 g (5.05 mmol) of 1H-indene-1,3(2H)-dione was added thereto, and then reacted at 50° C. for 2 hours to obtain 2.02 g (82.8% yield) of the compound represented by Chemical Formula 2-1. The obtained compound was purified to a purity of 99.9% by sublimation.

[0759] 1 H-NMR (500 MHz, dichloromethane-d 2 ): δ7.87(s,1H),7.72(m,6H),7.49(m,4H),7.34(m,3H),6.82(d,1H).

[0760] Synthesis Reference Example 2: Synthesis of the compound represented by Chemical Formula 2-2 (5-((5-(10H-phenoselenazine-10-yl)tellurophene-2-yl)methylene)-1,3-dimethyl-2-thiodihydropyrimidine-4,6(1H,5H)-dione)

[0761] [Chemical formula 2-2]

[0762]

[0763] [Reaction Scheme 2-2]

[0764]

[0765] (i) Synthesis of Compound 2-1A

[0766] 10.0 g (32.7 mmol) of 2-iodotellurophene and 6.17 g (25.2 mmol) of 10H-phenoselenazine were dissolved in 100 ml of anhydrous toluene in the presence of 5 mol% Pd(dba) 2 , 5 mol% P(tBu) 3 , and 2.66 g (27.7 mmol) of NaOtBu were heated under reflux for 2 hours. The obtained product was separated and purified by silica gel column chromatography (toluene: hexane volume ratio = 1: 4) to obtain 4.25 g (19.6% yield) of compound 2-1A (10-(tellurophen-2-yl)-10H-phenoselenazine).

[0767] (ii) Synthesis of Compound 2-1B

[0768] 1.84 ml of phosphoryl chloride was added dropwise to 6.0 ml of N, N-dimethylformamide at -15 ° C, and then stirred at room temperature (24 ° C) for 2 hours. The resultant was slowly added to a mixture of 180 ml of dichloromethane and 4.25 g of compound 2-1A at -15 ° C, then stirred at room temperature (24 ° C) for 30 minutes and concentrated under reduced pressure. Subsequently, 100 ml of water was added thereto, and an aqueous sodium hydroxide solution was added thereto until the pH became 14, and then stirred at room temperature (24 ° C) for 2 hours. The organic layer extracted by using dichloromethane was washed with an aqueous sodium chloride solution and then dried by adding anhydrous magnesium sulfate thereto. The obtained product was separated and purified by silica gel column chromatography (hexane: ethyl acetate volume ratio = 4: 1) to obtain 2.50 g (55.2% yield) of compound 2-1B (5- (10H- phenoselenazine-10-yl) tellurphene-2-carboxaldehyde).

[0769] (iii) Synthesis of the compound represented by Chemical Formula 2-2

[0770] 1.90 g (4.21 mmol) of compound 2-1B was suspended in ethanol, and 0.87 g (5.05 mmol) of 1,3-dimethyl-2-thiodihydropyrimidine-4,6 (1H, 5H) -dione was added thereto, and then reacted at 50° C. for 2 hours to obtain 2.02 g (yield = 79.2%) of the compound represented by Chemical Formula 2-2. The obtained compound was purified to a purity of 99.9% by sublimation.

[0771] 1 H-NMR (500 MHz, dichloromethane-d 2 ): δ8.29(s,1H),7.83(d,1H),7.73(d,2H),7.51(d,2H),7.37(t,2H),6.99(t,2H),5.32(d,1H),3.67(d,6H).

[0772] Synthesis Reference Example 3: Synthesis of the compound represented by Chemical Formula 2-3

[0773] [Chemical formula 2-3]

[0774]

[0775] [Reaction Scheme 2-3]

[0776]

[0777] (i) Synthesis of Compound 2-3A

[0778] 15.2 g (49.9 mmol) of 2-iodotellurophene and 7.6 g (41.6 mmol) of 10H-phen Oxazine was dissolved in 150 ml of anhydrous toluene in a 5 mol% Pd(dba) 2 , 5 mol% P(tBu) 3 , and 10.4 g (107.9 mmol) of NaOtBu were heated under reflux for 2 hours. The obtained product was separated and purified by silica gel column chromatography (toluene: hexane volume ratio = 1:4) to obtain 9.1 g (61.0% yield) of compound 2-3A (10-(tellurophene-2-yl)-10H-phen Oxazine).

[0779] (ii) Synthesis of Compound 2-3B

[0780] 1.25 ml (13.4 mmol) of phosphorus oxychloride was added dropwise to 4.0 ml (51.4 mmol) of N, N-dimethylformamide at -15°C, and then stirred at room temperature (24°C) for 2 hours. The obtained mixture was slowly added dropwise to a mixture of 200 ml of dichloromethane and 3.7 g (10.6 mmol) of compound 2-3A at -15°C, and then stirred at room temperature (24°C) for 2 hours. Subsequently, 100 ml of water was added thereto, and an aqueous sodium hydroxide solution was added thereto until the pH became 14, and then stirred at room temperature (24°C) for 2 hours. The organic layer extracted with dichloromethane was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The obtained product was separated and purified by silica gel column chromatography (volume ratio of hexane: ethyl acetate = 4:1) to obtain 3.5 g (88.0% yield) of compound 2-3B (5-(10H-phen (( ...tellurophene-2-yl(-10-oxazine-10-yl)tellurophene-2-carbaldehyde

[0781] (iii) Synthesis of the compound represented by Chemical Formula 2-3

[0782] 1.18g (3.0mmol) of compound 2-3B was suspended in ethanol, and 0.63g (3.6mmol) of 1,3-dimethyl-2-thiodihydropyrimidine-4,6 (1H, 5H) -dione was added thereto, and then heated at 50°C under reflux for 2 hours. The resultant was cooled to room temperature (24°C), and hexane was added thereto. When a powder was formed therein, the powder was filtered, and the product from the filtrate was then separated and purified by silica gel column chromatography (dichloromethane) to obtain 1.25g (83.0% yield) of the compound represented by chemical formula 2-3. The obtained compound was purified to a purity of 99.9% by sublimation.

[0783] 1 H-NMR (500 MHz, dichloromethane-d2): δ8.50 (s, 1H), 8.31 (d, 1H), 7.81 (d, 2H), 7.48 (t, 2H), 7.43-7.36 (m, 4H), 7.06 (d, 1H), 3.7 (d, 6H).

[0784] Synthesis Reference Example 4: Synthesis of the compound represented by Chemical Formula 2-4

[0785] [Chemical formula 2-4]

[0786]

[0787] [Reaction Scheme 2-4]

[0788]

[0789] (i) Synthesis of Compound 2-4A

[0790] 11.7 g (38.2 mmol) of 2-iodotellurophene and 6.3 g (31.8 mmol) of 10H-phenothiazine were dissolved in 150 ml of anhydrous toluene in the presence of 5 mol% Pd(dba) 2 , 5 mol% P(tBu) 3 , and 9.2 g (95.5 mmol) of NaOtBu were heated under reflux for 2 hours. The obtained product was separated and purified by silica gel column chromatography (volume ratio of toluene: hexane = 1:4) to obtain 7.0 g (yield 58.0%) of 10-(tellurophen-2-yl)-10H-phenothiazine.

[0791] (ii) Synthesis of Compound 2-4B

[0792] 1.6 ml (17.6 mmol) of phosphorus oxychloride was added dropwise to 5.3 ml (67.9 mmol) of N, N-dimethylformamide at -15 ° C, and then stirred at room temperature (24 ° C) for 2 hours. The resultant was slowly added dropwise to a mixture of 200 ml of dichloromethane and 5.1 g (13.6 mmol) of compound 2-4A at -15 ° C, and then stirred at room temperature (24 ° C) for 2 hours. Subsequently, 100 ml of water was added thereto, and a sodium hydroxide aqueous solution was added thereto until the pH became 14, and then stirred at room temperature (24 ° C) for 2 hours. The organic layer extracted with dichloromethane was washed with a sodium chloride aqueous solution and then dried by adding anhydrous magnesium sulfate thereto. The obtained product was separated and purified by silica gel column chromatography (volume ratio of hexane:ethyl acetate=4:1) to obtain 3.5 g (yield of 63.5%) of 5-(10H-phenothiazin-10-yl)tellurophene-2-carbaldehyde.

[0793] (iii) Synthesis of the compound represented by Chemical Formula 2-4

[0794] 1.09 g (2.7 mmol) of compound 2-4B was suspended in ethanol, and 0.55 g (3.2 mmol) of 1,3-dimethyl-2-thiodihydropyrimidine-4,6 (1H, 5H) -dione was added thereto, and then heated at 50 ° C under reflux for 2 hours. The resultant was cooled to room temperature (24 ° C), and hexane was added thereto. When a powder was formed therein, the powder was filtered, and then the product from the filtrate was separated and purified by silica gel column chromatography (dichloromethane) to obtain 1.30 g (87.0% yield) of the compound represented by chemical formula 2-4. The obtained compound was purified to a purity of 99.9% by sublimation.

[0795] 1H-NMR (500 MHz, dichloromethane-d2): δ8.50 (s, 1H), 8.31 (d, 1H), 7.81 (d, 2H), 7.48 (t, 2H), 7.55 (d, 2H), 7.36 (d, 2H), 7.04 (1, 2H), 3.7 (d, 6H).

[0796] Synthesis Reference Example 5: Synthesis of the compound represented by Chemical Formula 2-5

[0797] [Chemical formula 2-5]

[0798]

[0799] [Reaction Scheme 2-5]

[0800]

[0801]

[0802] (i) Synthesis of Compound 2-5A

[0803] 2.0 g (7.80 mmol) of 2-iodoselenophenol (Compound 1) and 1.2 g (7.09 mmol) of diphenylamine were dissolved in 30 ml of anhydrous toluene in the presence of 5 mol% Pd(dba) 2 , 5 mol% P(tBu) 3 , and 0.75 g (7.80 mmol) of NaOtBu were heated under reflux for 2 hours. The obtained product was separated and purified by silica gel column chromatography (toluene: hexane volume ratio = 1:4) to obtain 1.40 g (66.2% yield) of compound 2-5A.

[0804] (ii) Synthesis of Compound 2-5B

[0805] 1.75ml phosphoryl chloride is added dropwise to 6.0ml of N, N-dimethylformamide at -15°C, and then stirred at room temperature (24°C) for 2 hours. The obtained mixture is slowly added dropwise to a mixture of 60ml dichloromethane and 1.4g of compound 2-5A at -15°C, then stirred at room temperature (24°C) for 30 minutes and concentrated under reduced pressure. 100ml of water is added thereto, and sodium hydroxide aqueous solution is added thereto until pH becomes 14, and then stirred at room temperature (24°C) for 2 hours. The organic layer extracted with dichloromethane is washed with sodium chloride aqueous solution, and then dried by adding anhydrous magnesium sulfate thereto. The obtained product is separated and purified by silica gel column chromatography (hexane: ethyl acetate volume ratio = 4:1) to obtain 1.0g (65.3% yield) of compound 2-5B.

[0806] (iii) Synthesis of the compound represented by Chemical Formula 2-5

[0807] 0.33 g (1.09 mmol) of compound 2-5B was suspended in ethanol, and 0.23 g (1.3 mmol) of 1,3-dimethyl-2-thiodihydropyrimidine-4,6(1H,5H)-dione was added thereto, followed by reaction at 50° C. for 2 hours to obtain 0.47 g (90% yield) of the compound represented by Chemical Formula 2-5.

[0808] 1 H-NMR (500MHz, dichloromethane-d2): 8.5 (s, 1H), 7.9 (d, 1H), 7.5-7.3 (m, 10H), 6.6 (d, 1H), 3.7 (d, 6H)

[0809] Example 1: Fabrication of optoelectronic devices

[0810] ITO was deposited on a glass substrate by sputtering to form an anode of about 150 nm thick, and the ITO glass substrate was ultrasonically cleaned in acetone / isopropanol / pure water for 15 minutes, and then UV ozone cleaning was performed. Subsequently, the compound of Synthesis Example 1 and C60 were co-deposited on the ITO glass substrate in a volume ratio of 1:1 to form an active layer of 1000 nm thick, and Al was vacuum deposited thereon to a thickness of 70 nm to manufacture an optoelectronic device having a structure of ITO (150 nm) / active layer (1000 nm) / Al (70 nm).

[0811] Examples 2-4 and Reference Examples 1-5: Fabrication of Photoelectric Devices

[0812] Photoelectric devices of Examples 2 to 4 were manufactured according to the same method as Example 1, except that the compounds of Synthesis Examples 2 to 4 and Synthesis Reference Examples 1 to 5 were each used instead of the compound of Synthesis Example 1.

[0813] Evaluation 1: Light absorption properties of compounds

[0814] The light absorption characteristics (maximum absorption wavelength, half width (FWHM), and absorption coefficient of each film thickness) of the compounds of Synthesis Examples 1-4 were evaluated. Each compound of Synthesis Examples 1-4 (p-type semiconductor) and C60 (n-type semiconductor) were co-deposited at a volume ratio of 1:1 to form a film, and the light absorption characteristics of the film were evaluated in the ultraviolet-visible light (UV-Vis) region by using a Cary 5000UV spectrometer (Varian Medical Systems, Inc.). The results are shown in Table 1.

[0815] (Table 1)

[0816] Compound <![CDATA[λ 最大 (nm)]]> FWHM(nm) <![CDATA[Absorption coefficient (10 4 cm -1 )]]> Synthesis Example 1 532 85 7.65 Synthesis Example 2 543 90 7.43 Synthesis Example 3 530 86 7.01 Synthesis Example 4 542 91 6.98

[0817] Referring to Table 1, the compounds according to Synthesis Examples 1-4 exhibited a maximum absorption wavelength in the green wavelength region, a small full width at half maximum (FWHM), and a high absorption coefficient. Therefore, the compounds according to Synthesis Examples 1-4 have high wavelength selectivity in the green wavelength region.

[0818] Evaluation 2: Planarity of the compound

[0819] The molecular skeleton of the compound of synthetic example 1-4 and synthetic reference example 1-5 about the structure optimized on energy is calculated respectively by density functional theory (DFT), and in the corresponding skeleton, the ratio (Z / X) of the shortest length (Z) relative to the longest length (X) is calculated to obtain aspect ratio. The result is shown in Table 2.

[0820] (Table 2)

[0821]

[0822]

[0823] Referring to Table 2, the compound according to Synthesis Example 1-4 exhibits a low aspect ratio compared to the compound according to Synthesis Reference Example 1-5. Therefore, the compound according to Synthesis Example 1-4 maintains planarity.

[0824] Evaluation 3: Mobility evaluation of optoelectronic devices

[0825] In order to evaluate the mobility of the optoelectronic device, a 550 nm light (laser pulse (pulse width: 6 nm)) was irradiated into the optoelectronic device according to Examples 1-4 and Reference Examples 1-5, and a bias voltage (V) was applied thereto to measure its photocurrent. The time (t) at which the photocurrent was maximized was measured and used to calculate the mobility (μ) according to Equation 2.

[0826] [Equation 2]

[0827]

[0828] In Equation 2, T is the thickness of the active layer, t is the time when the photocurrent is maximized, and V is the applied voltage.

[0829] The results are shown in Table 3.

[0830] (Table 3)

[0831] Example <![CDATA[Mobility (cm 2 / V·s)]]> Example 1 <![CDATA[1.1×10 -5 ]]> Example 2 <![CDATA[1.0×10 -5 ]]> Example 3 <![CDATA[1.0×10 -5 ]]> Example 4 <![CDATA[1.0×10 -5 ]]> Reference Example 1 <![CDATA[0.1×10 -5 ]]> Reference Example 2 <![CDATA[0.1×10 -5 ]]> Reference Example 3 <![CDATA[0.2×10 -5 ]]> Reference Example 4 <![CDATA[0.2×10 -5 ]]> Reference Example 5 <![CDATA[0.2×10 -5 ]]>

[0832] Referring to Table 3, the optoelectronic devices of Examples 1-4, respectively including the compounds of Synthesis Examples 1-4, exhibited excellent mobility compared to the optoelectronic devices of Reference Examples 1-5, respectively including the compounds of Synthesis Reference Examples 1-5.

[0833] While some example embodiments have been described, it will be understood that the inventive concepts are not limited to the disclosed embodiments, but on the contrary are intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. The compound represented by chemical formula 2-1: [Chemical formula 2-1] in, In chemical formula 2-1, Y 1 -Y 4 Independently for CR p , where R p is hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, or the adjacent CR p are connected to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, X is O, S, Se, or Te, R 1 -R 3 are independently hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, or substituted or unsubstituted C1-C30 alkoxy, R 4 is hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, a is an integer from 0 to 4, and Ar 2 is a cyclic group represented by Chemical Formula 3: [Chemical formula 3] Among them, in chemical formula 3, Ar 2 ' is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group, Z 1 is O, S, Se, or Te, and Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or cyano, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group, The term "substituted" refers to that the hydrogen of the functional group is replaced by a substituent selected from the group consisting of F, Br, Cl, I, cyano, C1-C20 alkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, and combinations thereof.

2. The compound according to claim 1, wherein the compound is represented by one of Chemical Formulas 2-1A to 2-1D: [Chemical formula 2-1A] in, In Chemical Formula 2-1A, X、Ar 2 , R 1 -R 4 , and a are defined as in Chemical Formula 2-1 of claim 1, R 11 is hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, and a1 is an integer from 0 to 4, [Chemical formula 2-1B] Among them, in chemical formula 2-1B, X、Ar 2 , R 1 -R 4 , and a are defined as in Chemical Formula 2-1 of claim 1, R 11 are independently hydrogen, unsubstituted C1-C10 alkyl, or unsubstituted C1-C10 alkoxy, R 12 are independently hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, a1 is an integer from 0 to 4, and a2 is an integer from 0 to 2, [Chemical formula 2-1C] Among them, in chemical formula 2-1C, X、Ar 2 , R 1 -R 4 , and a are defined as in Chemical Formula 2-1 of claim 1, R 11 are independently hydrogen, unsubstituted C1-C10 alkyl, or unsubstituted C1-C10 alkoxy, R 12 are independently hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy, a1 is an integer from 0 to 4, and a2 is an integer from 0 to 2, [Chemical formula 2-1D] Among them, in chemical formula 2-1D, X、Ar 2 , R 1 -R 4 , and a are defined as in Chemical Formula 2-1 of claim 1, R 11 and R 12 are independently hydrogen, unsubstituted C1-C10 alkyl, or unsubstituted C1-C10 alkoxy, and a1 and a2 are independently integers of 0-4, The term "substituted" refers to that the hydrogen of the functional group is replaced by a substituent selected from the group consisting of F, Br, Cl, I, cyano, C1-C20 alkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, and combinations thereof.

3. The compound as claimed in claim 1, wherein in Chemical Formula 1, Ar 2 is a cyclic group represented by one of Chemical Formulae 4A to 4F: [Chemical Formula 4A] in, In Chemical Formula 4A, Z 1 is O, S, Se, or Te, Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or cyano, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group, Z 3 N or CR c , where R c is hydrogen, deuterium, or unsubstituted C1-C10 alkyl, R 11 , R 12 , R 13 , R 14 , and R 15 are the same or different and are independently hydrogen, deuterium, unsubstituted C1-C30 alkyl, halogen, or cyano, n is 0 or 1, and * is the connecting part, [Chemical Formula 4B] Wherein, in Chemical Formula 4B, Z 1 is O, S, Se, or Te, Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or cyano, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group, Z 3 O, S, Se, Te, or C(R a )(CN), where R a is hydrogen, cyano, or C1-C10 alkyl, R 11 and R 12 are independently hydrogen, deuterium, unsubstituted C1-C30 alkyl, unsubstituted C1-C30 alkoxy, halogen, or cyano, and * is the connecting part, [Chemical formula 4C] Among them, in chemical formula 4C, Z 1 is O, S, Se, or Te, Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or cyano, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group, R 11 , R 12 , and R 13 are the same or different and are independently hydrogen, deuterium, unsubstituted C1-C30 alkyl, unsubstituted C1-C30 alkoxy, halogen, or cyano, and * is the connecting part, [Chemical Formula 4D] Among them, in chemical formula 4D, Z 1 is O, S, Se, or Te, Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or cyano, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group, Z 3 N or CR c , where R c is hydrogen or unsubstituted C1-C10 alkyl, G 1 O, S, Se, Te, SiR x R y , or GeR z R w , where R x , R y , R z , and R w are the same or different and are independently hydrogen, halogen, or unsubstituted C1-C10 alkyl, R 11 , R 12 , and R 13 are the same or different and are independently hydrogen, deuterium, unsubstituted C1-C30 alkyl, unsubstituted C1-C30 alkoxy, halogen, or cyano, n is 0 or 1, and * is the connecting part, [Chemical formula 4E] Wherein, in Chemical Formula 4E, Z 1 is O, S, Se, or Te, Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or cyano, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group, Z 4 NR a , CR b R c ,O,S,Se,Te,S(=O),S(=O)2,SiR d R e , or GeR f R g , Where R a , R b , R c , R d , R e , R d , R e , R f , and R g are independently hydrogen or unsubstituted C1-C10 alkyl, G 2 O, S, Se, Te, SiR x R y , or GeR z R w , where R x , R y , R z , and R w are the same or different and are independently hydrogen, halogen, or unsubstituted C1-C10 alkyl, R 11 , R 12 , and R 13 are the same or different and are independently hydrogen, deuterium, unsubstituted C1-C30 alkyl, unsubstituted C1-C30 alkoxy, halogen, or cyano, n is 0 or 1, and * is the connecting part, [Chemical formula 4F] Wherein, in chemical formula 4F, Z 1 is O, S, Se, or Te, Z 2 O, S, Se, Te, or CR a R b , where R a and R b are independently hydrogen, substituted or unsubstituted C1-C10 alkyl, or cyano, and wherein when Z 2 CR a R b When R a and R b at least one of which is a cyano group, R 11 is hydrogen, deuterium, unsubstituted C1-C30 alkyl, halogen, or cyano, and G 3 O, S, Se, Te, SiR x R y , or GeR z R w , where R x , R y , R z , and R w are the same or different and are independently hydrogen, halogen, or unsubstituted C1-C10 alkyl, The term "substituted" refers to that the hydrogen of the functional group is replaced by a substituent selected from the group consisting of F, Br, Cl, I, cyano, C1-C20 alkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, and combinations thereof.

4. The compound of claim 3, wherein Ar 2 is a cyclic group represented by Chemical Formula 4A and Ar 2 represented by one of the chemical formulas 4A-1, 4A-2, or 4A-3, [Chemical Formula 4A-1] [Chemical Formula 4A-2] [Chemical Formula 4A-3] Wherein in Chemical Formulas 4A-1 and 4A-2, Z 3 , R 11 ,n,R 12 , R 13 , R 14 , and R 15 is the same as defined in Chemical Formula 4A of Claim 3, and Wherein in Chemical Formula 4A-3, Z 1 , Z 2 , Z 3 , R 11 , and n are defined as in Chemical Formula 4A of claim 3, R 12a and R 12b are independently hydrogen, deuterium, unsubstituted C1-C30 alkyl, halogen, or cyano, m1 and m2 are independently integers from 0 to 4, and Ph 1 and Ph 2 It is a fused phenylene ring.

5. The compound of claim 3, wherein Ar 2 is a cyclic group represented by Chemical Formula 4B and Ar 2 represented by one of the chemical formulas 4B-1, 4B-2, or 4B-3, in, In Formulae 4B-1, 4B-2, and 4B-3, R 11 and R 12 The definition of is the same as in Chemical Formula 4B of Claim 3.

6. The compound of claim 3, wherein Ar 2 is a cyclic group represented by Chemical Formula 4C and Ar 2 Represented by one of the chemical formulas 4C-1 or 4C-2, in, In chemical formulas 4C-1 and 4C-2, R 11 -R 13 The definition of is the same as in Chemical Formula 4C of Claim 3. 7 . The compound of claim 1 , wherein the compound represented by Chemical Formula 1 has an aspect ratio Z / X obtained by dividing the shortest length Z by the longest length X in a range of less than or equal to 0.

30. 8 . The compound according to claim 1 , wherein the compound has a maximum absorption wavelength in a wavelength range of greater than or equal to 500 nm and less than or equal to 590 nm in a thin film state.

9. The compound of claim 1, wherein the compound exhibits a light absorption curve having a full width at half maximum (FWHM) of 50 nm to 100 nm.

10. The compound of claim 1, wherein The compound represented by Chemical Formula 2-1 is a p-type semiconductor compound, The compound represented by Chemical Formula 2-1 has a HOMO energy level ranging from -5.2 eV to -5.8 eV and an energy band gap ranging from -2.12 eV to -2.48 eV, The LUMO energy level of the compound represented by Chemical Formula 2-1 is in the range of -3.7 eV to -2.7 eV, and The compound represented by Chemical Formula 2-1 has a molecular weight of 300 g / mol to 1500 g / mol.

11. An optoelectronic device comprising a first electrode and a second electrode facing each other, and an active layer between the first electrode and the second electrode, The active layer comprises the compound according to any one of claims 1 to 10.

12. An image sensor comprising: The photovoltaic device according to claim 11.

13. The image sensor of claim 12, further comprising: A semiconductor substrate having integrated therein a plurality of first light sensing devices configured to sense light in a blue wavelength region and a plurality of second light sensing devices configured to sense light in a red wavelength region, wherein The optoelectronic device is on the semiconductor substrate and is configured to selectively sense light in a green wavelength region.

14. The image sensor of claim 13, further comprising: A color filter layer includes a blue filter configured to selectively transmit light in a blue wavelength region and a red filter configured to selectively transmit light in a red wavelength region. 15 . The image sensor of claim 13 , wherein the first light-sensing device and the second light-sensing device are stacked in a vertical direction in the semiconductor substrate.

16. The image sensor according to claim 12, wherein the optoelectronic device is a green optoelectronic device and an organic optoelectronic device, and The image sensor further comprises: a blue optoelectronic device configured to selectively absorb light in a blue wavelength region; and a red optoelectronic device configured to selectively absorb light in a red wavelength region, The green optoelectronic device, the blue optoelectronic device, and the red optoelectronic device are stacked.

17. Electronic equipment, comprising: An image sensor as claimed in any one of claims 12 to 16.

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