Compounds and nonlinear-optically active organic materials, optical modulators and optical devices comprising the same

Abstract

Disclosed are compounds and nonlinear-optically active organic materials, optical modulators, and optical devices including the same. The compounds are represented by Chemical Formula 1. In Chemical Formula 1, the definitions of the groups and variables are as described in the DETAILED DESCRIPTION.

Description

[0001] Cross-reference to related applications

[0002] This application claims priority to and benefits from Korean Patent Application No. 10-2024-0186475, filed on December 13, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present invention relates to compounds and nonlinear optically active organic materials including the same, optical modulators, and optical devices. Background Technology

[0004] Recently, the rapid exchange of information via the Internet on computers has led to the globalization of information and communication between countries around the world. Ultra-high-speed information communication and the networks that include it can utilize optical communication, which uses relatively fast speeds, such as approximately 1000 Mbps. 14 Light vibrates at Hz and travels through optical fibers at a speed much faster than electrons. Optical communication, which involves encoding large amounts of information into light and transmitting that information rapidly, has been used in modern information communication.

[0005] An optical information processing system may include a light-emitting device that generates light, a photodetector that detects light, and an optical signal processing device that processes the optical signal. The optical signal processing device may include, for example, an optical switch and an optical modulator. Summary of the Invention

[0006] Example embodiments provide compounds that are thermally stable and have a high electro-optic coefficient (r). 33 It can be manufactured into a film using a simple process, making it suitable for use in optical communication devices (such as optical modulators).

[0007] Examples of embodiments provide nonlinear optically active organic materials comprising the compound.

[0008] Example implementations provide an optical modulator including the compound.

[0009] Example implementations provide optical devices that include the compound.

[0010] Example implementations provide electronic devices that include the compound or the optical modulator.

[0011] Optical modulators comprising the aforementioned compound, and any devices (e.g., optical devices) including the same, can (e.g., based on a combination of a continuous-wave laser and an external optical modulator) enable optical transmission configured (e.g., based on supporting modulation speeds exceeding approximately 10 Gbps) to transmit information for high-speed video communication applications such as video conferencing and high-definition television. Such optical modulators and any devices (e.g., optical devices) including the same can provide communication at higher speeds than optical transmission systems configured to transmit information based on direct modulation of semiconductor lasers (which enables modulation speeds up to approximately 2.5 Gbps). Optical modulators comprising the aforementioned compound and any devices (e.g., optical devices) including the same can exhibit superior processing performance and reduced manufacturing costs to meet the demands of such high-speed communication applications, thereby overcoming limitations that might otherwise exist due to the manufacturing costs of external optical modulators configured to support such high-speed communication applications, for example, due to difficulties in the manufacturing process of external optical modulators, such as those using inorganic crystals like LiNbO3.

[0012] According to some exemplary embodiments, the compound may be represented by chemical formula 1.

[0013] [Chemical Formula 1]

[0014]

[0015] In chemical formula 1,

[0016] Ar 1 Ar 2 And Ar 3 Each of these groups can be independently a substituted or unsubstituted C6 to C30 aromatic group, a substituted or unsubstituted C3 to C30 heteroaromatic group, or any combination thereof.

[0017] X 1 It can be a single bond, -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-(CR f R g ) n1 -、-CR ff R gg -、-C(Rm )=C(R n - or -C(R) p ) = N - (where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each of these can be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy, and R bb R cc R dd R ee R ff and R gg Each is independently (CH2) x Alternatively, heteroatoms such as O, N, S, Se, or Te may be present, where (CH2) x x is a positive integer, and R is a positive integer. bb and R cc The pair, R dd and R ee The pair, or R ff and R gg The pairs connect to each other to form the first ring structure, and in -(CR f R g ) n1 In the given information, n1 is either 1 or 2.

[0018] L can be a single bond, -O-, -S-, -Se-, -Te-, or -NR. a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-(CR f R g ) n1 -、-CR ff R gg -、-C(R m )=C(R n )-、-C(R mm )=C(Rnn - or -C(R) p ) = N - (where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each of these can be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy, and R bb R cc R dd R ee R ff R gg R mm and R nn Each is independently (CH2) y Alternatively, heteroatoms such as O, N, S, Se, or Te may be present, where (CH2) y In this context, y is a positive integer, and R is a positive integer. bb and R cc The pair, R dd and R ee The pair, R ff and R gg The pair, or R mm and R nn The pairs connect to each other to form a second ring structure, and in -(CR f R g ) n1 In the given information, n1 is either 1 or 2.

[0019] When L is -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1 -、-C(R m )=C(R n - or -C(R) p When )=N-, L is optionally connected to Ar. 1 Or Ar 2 To form a third ring structure,

[0020] Cy can be independently substituted or unsubstituted C6 to C10 arylene, substituted or unsubstituted C3 to C10 heteroarylene, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C3 to C10 cycloalkenyl, substituted or unsubstituted C3 to C10 heterocyclic alkyl, substituted or unsubstituted C3 to C10 heterocyclic alkenyl, or any combination thereof.

[0021] EWG can be used for CR a R b (where R) a and R b (Each group is independently a cyano or cyano-containing group); substituted or unsubstituted groups having a group selected from C=O, C=S, C=Se, C=Te, and CR a R b At least one functional group of a C6 to C30 hydrocarbon ring group (wherein R a and R b (Each group is independently a cyano or cyano-containing group); substituted or unsubstituted groups having a group selected from C=O, C=S, C=Se, C=Te, and CR a R b At least one functional group of a C2 to C30 heterocyclic group (wherein R a and R b Each group is independently a cyano group or a cyano-containing group; or any combination thereof.

[0022] R 1 To R 4 Each of these can independently be hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, substituted or unsubstituted C2 to C30 acyl, halogen, cyano (-CN), cyano-containing group, nitro, pentafluorothioalkyl (-SF5), hydroxyl, amino, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphate or its salt, -SiR a R b R c (where R) a R b and R c Each of the following is independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, or any combination thereof.

[0023] x can be an integer from 0 to 5.

[0024] y can be an integer from 1 to 5.

[0025] z can be an integer from 0 to 5, and

[0026] n can be an integer from 1 to 5.

[0027] A compound represented by chemical formula 1 may also be a compound represented by chemical formula 2.

[0028] [Chemical Formula 2]

[0029]

[0030] In chemical formula 2, EDG can be the electron donor portion represented by chemical formula 2A:

[0031] [Chemical Formula 2A]

[0032]

[0033] In chemical formula 2 and chemical formula 2A,

[0034] X 1 L, Cy, Ar 3 R 1 To R 4 EWG, x, y, z, and n are the same as in chemical formula 1.

[0035] Y 1 To Y 7 Each can be N or CR independently. k , where R k It is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C1 to C10 alkoxy, or adjacent R k They can be linked together to form substituted or unsubstituted C6 to C30 aromatic groups, substituted or unsubstituted C3 to C30 heteroaromatic groups, or their fused rings, and

[0036] * indicates the connection point with chemical formula 2.

[0037] In chemical formula 2A, Y 4 Can be N or CR k (where R) k (or halogen, cyano, C1 to C10 haloalkyl, C1 to C10 cyanoalkyl, or amino)

[0038] Y 7 Can be N or CR k (where R) k It can be halogen, cyano, C1 to C10 haloalkyl, C1 to C10 cyanoalkyl, or amino), and X 1 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeRd R e -、-(CR f R g ) n1 -、-C(R m )=C(R n - or -C(R) p ) = N - (where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each can be independently a halogen, a C1 to C20 haloalkyl, or a C1 to C20 cyanoalkyl, and wherein -(CR f R g ) n1 - where n1 is 1 or 2).

[0039] In chemical formula 2A, when Y 1 To Y 7 The two adjacent ones are CR k At that time, two adjacent CRs k They can connect to each other to form fused rings (fused loops).

[0040] In this case, EDG, represented by chemical formula 2A, can be represented by chemical formula 2AA.

[0041] [Chemical formula 2AA]

[0042]

[0043] In the chemical formula 2AA,

[0044] X 1 L, Y 1 To Y 7 And Ar 3 Same as in chemical formula 2A,

[0045] X 11 With X in chemical formula 1 1 Same, and

[0046] * indicates the adjacent (C(R)) of chemical formula 2. 1 )=C(R 2 )) x Or (Cy) y Connection points of functional groups.

[0047] In chemical formula 1, the first ring structure and the second ring structure can each be independently a spirocyclic structure or a fused ring structure.

[0048] The helical structure may include one of the multiple parts represented by group 1.

[0049] [Group 1]

[0050]

[0051] In group 1,

[0052] X a and X b They can be independently -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、or-GeR dd R ee - (where R) a1 R a2 R b R c R d and R e Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy, and R bb R cc R dd and R ee Each is independently (CH2) z Alternatively, heteroatoms such as O, N, S, Se, or Te may be present, where (CH2) z In this context, z is a positive integer, and R is a positive integer. bb and R cc The pair or R dd and R ee (The elements connect to each other to form a third ring structure),

[0053] L a Can be -O-, -S-, -Se-, -Te-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e-、-(CR f R g ) n1 -、-C(R p ) = N-, or single bond (where R a1 R a2 R b R c R d R e R f R g and R p Each of these can be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy, and wherein -(CR f R g ) n1 - where n1 is 1 or 2), and

[0054] One or more hydrogens in each ring may optionally be replaced by at least one substituent selected from: deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, and substituted or unsubstituted C6 to C20 aryloxy.

[0055] In group 1, CH in the aromatic rings present in parts (3), (4), (5), (6) and (7) can be replaced by N.

[0056] In chemical formula 1, Ar 3 It can be any one of the multiple parts represented by group 2.

[0057] [Group 2]

[0058]

[0059] In group 2,

[0060] X 21 and X 23 They can each independently be single bonds, -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f Rg - or -CR ff R gg - (where R) a1 R a2 R b R c R d R e R f and R g Each of these can be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy, and R bb R cc R dd R ee R ff and R gg Each is independently (CH2) w Alternatively, heteroatoms such as O, N, S, Se, or Te may be present, where (CH2) w In this context, w is a positive integer, and R is a positive integer. bb and R cc The pair, R dd and R ee The pair, or R ff and R gg (The elements connect to each other to form a third ring structure),

[0061] R 21 It can be hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, substituted or unsubstituted C2 to C30 acyl, halogen, cyano (-CN), cyano-containing group, nitro, pentafluorothioalkyl (-SF5), hydroxyl, amino, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphate or its salt, -SiR a R b R c (where R) a R b and R c Each of the following is independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, or any combination thereof.

[0062] Y 21 To Y 28 Each can be N or CR independently. k , where R kIt can be hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C1 to C10 alkoxy, or adjacent R k They can be linked together to form substituted or unsubstituted C6 to C30 aromatic groups, substituted or unsubstituted C3 to C30 heteroaromatic groups, or fused rings thereof, provided that Y in part (4) is present. 21 To Y 24 Y in any one of the parts (5) 25 To Y 28 Y in any one of the parts (6) 25 To Y 28 Y in any one or part of (7) 25 To Y 28 Any one of them is a group that connects a single bond, more precisely, the group adjacent to the (C(R) group in formula 1. 1 )=C(R 2 )) x Or (Cy) y Groups linked by groups,

[0063] *=* represents the presence of X in chemical formula 1. 1 The ring-fused portion, and

[0064] -* indicates the (C(R) adjacent to chemical formula 1. 1 )=C(R 2 )) x Or (Cy) y Connection points of functional groups.

[0065] In chemical formula 1, Cy can be any of the multiple parts represented by group 3. When there are two or more Cy, each Cy can be the same or different and can be independently selected from group 3.

[0066] [Group 3]

[0067]

[0068] In group 3,

[0069] Z 11 Z 12 and Z 13 Each can be independently represented as O, S, Se, Te, S(=O), S(=O)2, NR a or SiR b R c (where R) a R b and R cEach of these can be independently hydrogen, C1 to C10 alkyl, C1 to C10 haloalkyl, -SiH3, C1 to C10 alkylsilyl, -NH2, C1 to C10 alkylamino, C6 to C12 aryl, C3 to C12 heteroaryl, halogen, cyano, or any combination thereof.

[0070] Z 20 and Z 21 Each can be independently O, S, Se, or Te.

[0071] R b and R c They can exist independently or be connected to form a third ring structure, and

[0072] * indicates the connection point with chemical formula 1.

[0073] In chemical formula 1, EWG can be a cyclic group represented by chemical formula 3.

[0074] [Chemical Formula 3]

[0075]

[0076] In chemical formula 3,

[0077] EWG' can be a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C3 to C30 heteroaryl, or a substituted or unsubstituted C3 to C30 heterocyclic alkenyl.

[0078] Z can be O, S, Se, Te, or CR a R b , where R a and R b Each is independently a cyano group or a cyano-containing group, and

[0079] * indicates the connection point with chemical formula 1.

[0080] In chemical formula 1, EWG can be any cyclic group represented by chemical formula 3A to chemical formula 3G.

[0081] [Chemical Formula 3A]

[0082]

[0083] In chemical formula 3A,

[0084] Z 1 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be an independent cyano group or a cyano-containing group.

[0085] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each of these groups can be independently hydrogen, substituted or unsubstituted C1 to C10 alkyl groups, cyano groups, or cyano-containing groups.

[0086] Z 3 Can be N and CR c (where R) c (It is hydrogen, deuterium, or substituted or unsubstituted C1 to C10 alkyl groups),

[0087] R 11 R 12 R 13 R 14 and R 15 They may be the same or different and may each independently be hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), cyano-containing groups, or any combination thereof, wherein R 12 and R 13 and R 14 and R 15 They can exist independently or connect with each other to form dense aromatic rings.

[0088] n can be 0 or 1, and

[0089] * indicates the connection point with chemical formula 1.

[0090] [Chemical Formula 3B]

[0091]

[0092] In the chemical formula 3B,

[0093] Z 1 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be an independent cyano group or a cyano-containing group.

[0094] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each of these groups can be independently hydrogen, substituted or unsubstituted C1 to C10 alkyl groups, cyano groups, or cyano-containing groups.

[0095] Z 3 It can be O, S, Se, Te, or C(R) a (CN)(where R) a It can be hydrogen, cyano (-CN), or C1 to C10 alkyl.

[0096] R 11 and R 12 Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), or any combination thereof, and

[0097] * indicates the connection point with chemical formula 1.

[0098] [Chemical formula 3C]

[0099]

[0100] In the chemical formula 3C,

[0101] Z 1 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be an independent cyano group or a cyano-containing group.

[0102] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each of these groups can be independently hydrogen, substituted or unsubstituted C1 to C10 alkyl groups, cyano groups, or cyano-containing groups.

[0103] R 11 R 12 and R 13 They may be the same or different and may each independently be hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), or any combination thereof, and

[0104] * indicates the connection point with chemical formula 1.

[0105] [Chemical Formula 3D]

[0106]

[0107] In chemical formula 3D,

[0108] Z 1 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be an independent cyano group or a cyano-containing group.

[0109] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each of these groups can be independently hydrogen, substituted or unsubstituted C1 to C10 alkyl groups, cyano groups, or cyano-containing groups.

[0110] Z 3 Can be N or CR c (where R) c It can be hydrogen or substituted or unsubstituted C1 to C10 alkyl groups.

[0111] G 1 It can be O, S, Se, Te, SiR x R y , or GeR z R w , where R x R y R z and R w They may be the same or different and may each be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, or substituted or unsubstituted C6 to C20 aryl.

[0112] R 11 R 12 and R 13 It may be the same or different and may be independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano, cyano-containing group, or any combination thereof, wherein R 12 and R 13 They can exist independently or connect with each other to form dense aromatic rings.

[0113] n can be 0 or 1, and

[0114] * indicates the connection point with chemical formula 1.

[0115] [Chemical formula 3E]

[0116]

[0117] In the chemical formula 3E,

[0118] Z 1 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be an independent cyano group or a cyano-containing group.

[0119] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each of these groups can be independently hydrogen, substituted or unsubstituted C1 to C10 alkyl groups, cyano groups, or cyano-containing groups.

[0120] Z 3 Can be N or CR c (where R) c It can be hydrogen or substituted or unsubstituted C1 to C10 alkyl groups.

[0121] G 2 It can be O, S, Se, Te, SiR x R y , or GeR z R w , where R x R y R z and R w They may be the same or different and may each be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, or substituted or unsubstituted C6 to C20 aryl.

[0122] R 11 R 12 and R 13 They may be the same or different and may each independently be hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano, cyano-containing groups, or any combination thereof.

[0123] n can be 0 or 1, and

[0124] * indicates the connection point with chemical formula 1.

[0125] [Chemical formula 3F]

[0126]

[0127] In the chemical formula 3F,

[0128] Z 1 It can be O, S, Se, Te, or CR a R b , where R a and R b Each can be an independent cyano group or a cyano-containing group.

[0129] Z 2 It can be O, S, Se, Te, or CR a R b , where R a and R b Each of these groups can be independently hydrogen, substituted or unsubstituted C1 to C10 alkyl groups, cyano groups, or cyano-containing groups.

[0130] R 11 It can be hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), cyano-containing groups, or any combination thereof, and

[0131] G 3 It can be O, S, Se, Te, SiR x R y , or GeR z R w , where R x R y R z and R w They may be the same or different and each independently be hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, or substituted or unsubstituted C6 to C20 aryl, and

[0132] * indicates the connection point with chemical formula 1.

[0133] [Chemical formula 3G]

[0134]

[0135] In the chemical formula 3G,

[0136] Z 1 It can be O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group.

[0137] R 11 To R 13It can be hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), cyano-containing groups, or any combination thereof, and

[0138] G 3 It can be O, S, Se, Te, SiR x R y , or GeR z R w , where R x R y R z and R w They may be the same or different and may each be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, or substituted or unsubstituted C6 to C20 aryl, and

[0139] * indicates the connection point with chemical formula 1.

[0140] The compound may have a hyperpolarizability of less than or equal to about -170.

[0141] The compound may have a dipole moment greater than or equal to about 15 Debye.

[0142] The compound may have a glass transition temperature of less than or equal to about 150°C.

[0143] According to some exemplary embodiments, nonlinear optically active organic materials may include compounds represented by chemical formula 1.

[0144] According to some exemplary embodiments, the optical modulator may include: a compound represented by chemical formula 1, and / or a nonlinear optically active organic material comprising a compound represented by chemical formula 1.

[0145] According to some exemplary embodiments, the optical modulator may include: a first electrode and a second electrode facing each other; and an active layer between the first electrode and the second electrode, wherein the active layer comprises a compound represented by chemical formula 1.

[0146] The optical modulator may further include a charge blocking layer between the first electrode and the active layer.

[0147] The active layer may further include a matrix polymer, a photoconductive polymer, a photosensitizer, or any combination thereof.

[0148] According to some exemplary embodiments, an optical device may include: an input section (segment), a branch section, a waveguide, a combination section, and an output section. The waveguide may include an optical modulator. The optical modulator may include: a first electrode and a second electrode facing each other, and an active layer between the first electrode and the second electrode, wherein the active layer comprises a compound represented by Chemical Formula 1.

[0149] The compound is thermally stable and has a high electro-optic coefficient (r). 33 The compound can be manufactured into a film using a simple process, and therefore the compound is suitable for use in optical communication devices (which may also be referred to interchangeably as "optical devices" herein) (e.g., including optical modulators), and enables the realization of optical devices (e.g., including optical modulators) that enable high-speed communication via optical transmission at a reduced manufacturing cost based on the inclusion of the compound. Attached Figure Description

[0150] Figure 1 This is a schematic diagram showing the usage of an optical modulator in an optical communication device, such as a Mach-Zehnder interferometer, according to some exemplary embodiments.

[0151] Figure 2 This is a cross-sectional view of an optical modulator according to some exemplary embodiments.

[0152] Figure 3 These are schematic diagrams of electronic devices implemented according to some examples. Detailed Implementation

[0153] The following describes some exemplary implementations in detail so that those skilled in the art can readily implement them. However, practical applications can be implemented in many different forms and are not limited to the exemplary implementations described herein.

[0154] In the accompanying drawings, the thicknesses of layers, films, panels, regions, etc., are enlarged for clarity. The same reference numerals denote the same elements throughout the specification. It will be understood that when an element, such as a layer, film, region, or substrate, is referred to as being "on" another element, it may be directly on said other element, or there may be intermediate elements present. Conversely, when an element is referred to as being "directly on" another element, there are no intermediate elements.

[0155] In the accompanying drawings, for clarity of implementation, parts unrelated to the description have been omitted, and identical or similar constituent elements are indicated by the same reference numerals throughout the specification.

[0156] As used herein, “at least one of A, B or C”, “A, B, C, or any combination thereof” and “A, B, C, or any combination thereof” refer to each of the constituent elements and any combination thereof (e.g., A; B; C; A and B; A and C; B and C; or A, B and C).

[0157] As used herein, unless otherwise specifically defined, “substituted” means that the hydrogen atom of a compound or functional group is replaced by: a halogen atom (F, Br, Cl, or I), a hydroxyl group, a nitro group, a cyano group, an azide group, an amido group, an amino group (-NR'R'', where R' and R'' are the same or different, and are hydrogen atoms, C1 to C20 alkyl, silyl, C1 to C20 alkylsilyl, C6 to C30 aryl, (C1 to C20 alkyl)(diC6 to C10 aryl)silyloxy(C1 to C20)alkyl, or C7 to C30 alkylaryl. Silyl, hydrazine, hydrazone, acyl, carbamoyl, thiol, ester, carboxyl or salt thereof, sulfonic acid or salt thereof, phosphate or salt thereof, C1 to C20 alkyl, C1 to C20 alkoxy, C2 to C20 alkenyl, C2 to C20 alkynyl, C6 to C30 aryl, C7 to C30 arylalkyl, C2 to C20 heteroaryl, C3 to C20 heteroarylalkyl, C3 to C30 (e.g., C3 to C20 or C3 to C10) cycloalkyl, C3 to C15 cycloalkenyl, C6 to C15 cycloalkynyl, C2 to C20 heterocycloalkyl, or any combination thereof.

[0158] "Aromatic group" refers to a hydrocarbon ring group having an aromatic ring, including monocyclic and polycyclic hydrocarbon ring groups, and the other ring of the polycyclic hydrocarbon ring group can be an aromatic ring or a non-aromatic ring. Aromatic groups can be C6 to C30 aromatic groups, C6 to C20 aromatic groups, or C6 to C10 aromatic groups.

[0159] "Heteroaromatic group" refers to an aromatic group that includes 1 to 3 heteroatoms selected from N, O, S, P, and Si in the ring. Heteroaromatic groups can be C3 to C30 heteroaromatic groups, C3 to C20 heteroaromatic groups, or C3 to C10 heteroaromatic groups.

[0160] As used herein, "hydrocyclic group" can be a C3 to C30 hydrocarbon cyclic group. The hydrocarbon cyclic group can be an aromatic hydrocarbon cyclic group (e.g., a C6 to C30 aromatic group, a C6 to C20 aromatic group, or a C6 to C10 aromatic group, or a C6 to C30 aryl, a C6 to C20 aryl, or a C6 to C10 aryl), an alicyclic hydrocarbon cyclic group (e.g., a C3 to C30 cycloalkyl, a C5 to C30 cycloalkyl, a C3 to C20 cycloalkyl, or a C3 to C10 cycloalkyl), or a fused cyclic group thereof. For example, a fused ring group can refer to a fused ring of an aromatic ring (aromatic ring) and a non-aromatic ring (alicyclic ring), such as a fused ring in which at least one aromatic ring (aromatic ring) such as a C6 to C30 aromatic group, a C6 to C20 aromatic group, or a C6 to C10 aromatic group, or a C6 to C30 aryl, a C6 to C20 aryl, or a C6 to C10 aryl and at least one non-aromatic ring (alicyclic ring) such as a C3 to C30 cycloalkyl, a C3 to C20 cycloalkyl, or a C3 to C10 cycloalkyl is fused with each other.

[0161] As used herein, "heterocyclic group" can be a C2 to C30 heterocyclic group. A heterocyclic group can be a cyclic group in which at least one, for example one to three, carbon atoms of an aromatic cyclic group (e.g., C6 to C30 aromatic group, C6 to C20 aromatic group, or C6 to C10 aromatic group, or C6 to C30 aryl, C6 to C20 aryl, or C6 to C10 aryl), an alicyclic cyclic group (e.g., C3 to C30 cycloalkyl, C3 to C20 cycloalkyl, or C3 to C10 cycloalkyl), or a fused cyclic group is replaced by a heteroatom selected from N, O, S, P, and Si. Alternatively or concurrently, at least one carbon atom of the heterocyclic group may be replaced by a carbonyl group (C=O) or a thiocarbonyl group (C=S).

[0162] As used herein, unless otherwise specifically defined, “hybrid” means one to three heteroatoms selected from N, O, S, P, and Si.

[0163] As used in this article, "alkyl" refers to a monovalent straight-chain or branched saturated hydrocarbon group, such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, etc.

[0164] As used herein, “cycloalkyl” refers to a monovalent saturated hydrocarbon cyclic group in which the ring atom is carbon, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

[0165] As used herein, “heterocyclic alkyl” means a group in which one or more carbon atoms in a cycloalkyl group are each independently replaced by a heteroatom selected from N, O, S, P, and Si, a carbonyl group (C=O), and / or a thiocarbonyl group (C=S). As used herein, “hemiecyclic alkyl” means a divalent group having the same structure as a heterocyclic alkyl group.

[0166] As used herein, "aryl" refers to a substituent in which all cyclic atoms have conjugated p orbitals and can be monocyclic, polycyclic, or fused polycyclic (e.g., a ring sharing adjacent carbon pairs) functional groups.

[0167] As used herein, unless otherwise defined, "cyano-containing group" means a monovalent group in which at least one hydrogen atom is replaced by a cyano group, such as a C1 to C30 (e.g., C1 to C20 or C1 to C10) alkyl, C2 to C30 (e.g., C2 to C20 or C2 to C10) alkenyl, or C2 to C30 (e.g., C2 to C20 or C2 to C10) ynyl. A cyano-containing group also refers to a divalent group, such as =CR. x' -(CR x R y ) p -CR y' (CN)2, where R x R y R x' and R y' Each is independently hydrogen or a C1 to C10 alkyl group, and p is an integer from 0 to 10 (or 1 to 10). Specific examples of cyano-containing groups include dicyanomethyl, dicyanovinyl, cyanoethynyl, etc. As used herein, cyano-containing groups do not include functional groups containing only a cyano (-CN) group.

[0168] As used herein, unless otherwise defined, "aromatic ring" refers to a C6 to C10 cyclic group (e.g., C6 to C10 aryl) that provides a conjugated structure or a C2 to C10 heterocyclic group (e.g., C2 to C10 heteroaryl) that provides a conjugated structure.

[0169] As used herein, unless otherwise defined, "spirocyclic structure" can be any structure including X in Formula 1. 1The L-ring may be a substituted or unsubstituted C3 to C30 (e.g., C5 to C30) hydrocarbon cyclic group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a fused ring thereof, sharing one atom. The substituted or unsubstituted C3 to C30 (e.g., C5 to C30) hydrocarbon cyclic group may be, for example, a substituted or unsubstituted C3 to C30 (e.g., C5 to C30) cycloalkyl (e.g., substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C5 to C20 cycloalkyl, or substituted or unsubstituted C5 to C10 cycloalkyl); a substituted or unsubstituted C6 to C30 aryl (e.g., substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C10 aryl); or a substituted or unsubstituted C3 to C30 (e.g., C5 to C30) cycloalkyl (e.g., substituted or unsubstituted...). The fused ring of C3 to C20 cycloalkyl, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C5 to C20 cycloalkyl, or substituted or unsubstituted C5 to C10 cycloalkyl) and substituted or unsubstituted C6 to C30 aryl (e.g., substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C10 aryl), and the substituted or unsubstituted C2 to C30 heterocyclic group may be, for example, substituted or unsubstituted C2 to C20 heterocyclic alkyl (e.g., substituted or unsubstituted C2 to C10 heterocyclic alkyl) or substituted or unsubstituted C2 to C20 heteroaryl (e.g., substituted or unsubstituted C2 to C10 heteroaryl).

[0170] As used herein, unless otherwise defined, a “fused ring” is a fused ring of two or more substituted or unsubstituted C5 to C30 hydrocarbon ring groups (e.g., fluorenyl), a fused ring of two or more substituted or unsubstituted C2 to C30 heterocyclic groups, or a fused ring of a substituted or unsubstituted C5 to C30 hydrocarbon ring group and a substituted or unsubstituted C2 to C30 heterocyclic group (e.g., carbazole). In this document, hydrocarbon ring groups and heterocyclic groups are as defined above.

[0171] As used herein, unless otherwise defined, “halogen” can be any of F, Cl, Br, and I, and a haloalkyl is a group in which at least one hydrogen atom of the alkyl group is replaced by a halogen, and can be, for example, a perfluoroalkyl group such as -CF3.

[0172] As used herein, unless otherwise defined, an amino group may be a substituent represented by -NR'R'' (where R' and R'' are the same or different and are hydrogen atoms, C1 to C20 alkyl, silyl, C1 to C20 alkylsilyl, C6 to C30 aryl, or C7 to C30 alkylarylsilyl).

[0173] As used herein, unless otherwise defined, “combination” can include mixtures, alloys, or stacked structures of two or more.

[0174] As used herein, unless otherwise defined, “combination” in the definition of a functional group means substitution in which one substituent is replaced by another substituent, fusion with each other, or linkage with each other by a single bond or C1 to C10 alkylene groups.

[0175] It will be understood that elements and / or properties described herein as “the same,” “identical,” or “equal” to other elements and / or their properties, and it will be further understood that elements and / or their properties described herein as “the same,” “identical,” or “equal” to other elements and / or their properties may be “the same,” “identical,” or “equal” to other elements and / or their properties, or “substantially the same,” “substantially identical,” or “substantially equal.” Elements and / or their properties that are “substantially the same,” “substantially identical,” or “substantially equal” to other elements and / or their properties will be understood to include elements and / or their properties that are the same, identical, or equal to other elements and / or their properties within manufacturing tolerances and / or material tolerances. Elements and / or their properties that are the same or substantially the same, equal, or substantially equal to other elements and / or their properties, and / or the same or substantially identical may be structurally the same or substantially the same, functionally the same or substantially the same, and / or compositionally the same or substantially the same. While the terms “the same,” “equal,” or “the same” may be used in the description of some exemplary embodiments, it should be understood that some imprecision may exist. Therefore, when an element or property is described as being the same, equal, or identical to another element or property, it should be understood that the element or property is identical to the other element or property within the expected range of manufacturing or operational tolerances (e.g., ±10%).

[0176] It will be understood that elements and / or properties described herein as “substantially” identical, equal, and / or the same encompass elements and / or properties having a relative difference in size equal to or less than 10%. Furthermore, regardless of whether elements and / or properties are modified with “substantially,” it will be understood that such elements and / or properties should be interpreted to include manufacturing or operational tolerances (e.g., ±10%) surrounding the stated elements and / or properties.

[0177] When the terms “about” or “substantially” are used in this specification with respect to numerical values, it is intended that the relevant numerical value includes manufacturing or operational tolerances (e.g., ±10%) around the stated numerical value. Similarly, when the terms “about” and “substantially” are used with respect to geometry, it is intended that precision of the geometry is not required, but tolerance for shape is permitted within the scope of this disclosure. Furthermore, regardless of whether a numerical value or shape is modified by “about” or “substantially,” it will be understood that these values ​​and shapes should be interpreted as including manufacturing or operational tolerances (e.g., ±10%) around the stated numerical value or shape. When ranges are detailed, the range includes all values ​​within that range, for example, in increments of 0.1%.

[0178] As described herein, when an operation is described as being performed "via" or "through" an additional operation, or an effect, such as a structure, is described as being established "via" or "through" an additional operation, it will be understood that the operation may be performed "based on" the additional operation and / or the effect / structure may be established "based on" the additional operation, which may include performing the additional operation alone or in combination with other further additional operations.

[0179] The following describes compounds according to some exemplary embodiments. These compounds are represented by Chemical Formula 1.

[0180] [Chemical Formula 1]

[0181]

[0182] In chemical formula 1,

[0183] Ar 1 Ar 2 And Ar 3 Each of these groups can be independently a substituted or unsubstituted C6 to C30 aromatic group, a substituted or unsubstituted C3 to C30 heteroaromatic group, or any combination thereof (e.g., fused ring).

[0184] X 1 It can be a single bond, -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-(CR f R g ) n1-、-CR ff R gg -、-C(R m )=C(R n - or -C(R) p ) = N - (where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy, and R bb R cc R dd R ee R ff and R gg Each can be independently (CH2) x Alternatively, heteroatoms such as O, N, S, Se, or Te may be present, where (CH2) x In this context, x is a positive integer (e.g., any positive integer, such as 1 to 5, or 2 to 3), and R is a positive integer. bb and R cc The pair, R dd and R ee The pair, or R ff and R gg The pairs can be connected to each other to form a ring structure, wherein such a ring structure is interchangeably referred to as the "first ring structure" in this paper, and in -(CR f R g ) n1 In the given information, n1 is either 1 or 2.

[0185] L can be a single bond, -O-, -S-, -Se-, -Te-, or -NR. a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-(CR f R g ) n1 -、-CRff R gg -、-C(R m )=C(R n )-、-C(R mm )=C(R nn - or -C(R) p ) = N - (where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy, and R bb R cc R dd R ee R ff R gg R mm and R nn Each can be independently (CH2) y Alternatively, heteroatoms such as O, N, S, Se, or Te may be present, where (CH2) y In this context, y is a positive integer (e.g., any positive integer, such as 1 to 5, or 2 to 3), and R is a positive integer. bb and R cc The pair, R dd and R ee The pair, R ff and R gg The pair, or R mm and R nn The pairs can be connected to each other to form a ring structure, wherein such a ring structure is interchangeably referred to as a "second ring structure" in this paper, and in -(CR f R g ) n1 In the given information, n1 is either 1 or 2.

[0186] When L is -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1-、-C(R m )=C(R n - or -C(R) p When )=N-, L can be optionally connected to Ar. 1 Or Ar 2 This forms a ring structure, which can be interchangeably referred to as the "third ring structure" in this paper.

[0187] Cy can be independently substituted or unsubstituted C6 to C10 arylene, substituted or unsubstituted C3 to C10 heteroarylene, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C3 to C10 cycloalkenyl, substituted or unsubstituted C3 to C10 heterocyclic alkyl, substituted or unsubstituted C3 to C10 heterocyclic alkenyl, or any combination thereof.

[0188] EWG can be used for CR a R b (where R) a and R b (Each group is independently a cyano or cyano-containing group); substituted or unsubstituted groups having a group selected from C=O, C=S, C=Se, C=Te, and CR a R b At least one functional group of a C6 to C30 hydrocarbon ring group (wherein R a and R b (Each group can be independently a cyano or cyano-containing group); substituted or unsubstituted groups having a group selected from C=O, C=S, C=Se, C=Te, and CR a R b At least one functional group of a C2 to C30 heterocyclic group (wherein R a and R b Each group can be an independent cyano group or a cyano-containing group; or any combination thereof.

[0189] R 1 To R 4 Each of these can independently be hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, substituted or unsubstituted C2 to C30 acyl, halogen, cyano (-CN), cyano-containing group, nitro, pentafluorothioalkyl (-SF5), hydroxyl, amino, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphate or its salt, -SiR a R b R c (where R) a R b and R cEach of them may be independently hydrogen or substituted or unsubstituted C1 to C10 alkyl groups, or any combination thereof.

[0190] x can be an integer from 0 to 5.

[0191] y can be an integer from 1 to 5.

[0192] z can be an integer from 0 to 5, and

[0193] n can be an integer from 1 to 5.

[0194] In Formula 1, Cy can be a substituted C3 to C10 cyclic alkenyl group or a substituted C3 to C10 heterocyclic alkenyl group, and Cy can have an exocyclic alkylidene (e.g., methylidene) as a substituent. In this case, in addition to the C3 to C10 cyclic alkenyl group or C3 to C10 heterocyclic alkenyl group in Cy, the exocyclic alkylidene group can be further linked to C(R) 3 )=C(R 4 ) group, thus (C(R) 1 )=C(R 2 )) x (Cy) y 、 and (C(R) 3 )=C(R 4 )) z Together they form a conjugated polyene structure, as illustrated in the examples described later by compounds represented by chemical formulas 1-5, 1-6, or 1-11.

[0195] In Formula 1, the substituted C6 to C30 hydrocarbon ring or the substituted C2 to C30 heterocycle in EWG may have an exocyclic alkylidene group (e.g., a methylene group) as a substituent. In this case, the exocyclic alkylidene group may be attached to C(R) 3 )=C(R 4 ) or (Cy) y Examples of this can be illustrated by the compounds represented by Formulas 1-4 in the embodiments described later. The compound represented by Formula 1 can be usefully used as a nonlinear optically active organic material in optical signal processing devices. A nonlinear optically active organic material is a material whose optical properties, such as phase, change when light passes through it. For example, when a nonlinear optically active organic material is applied to a Mach-Zehnder (MZI) optical modulator, its refractive index changes when an electric field is applied, and the phase of light passing through it is modulated.

[0196] The compound has a D-π-A structure and includes: an electron donor moiety (D) comprising a first ring moiety containing nitrogen (N) and L, and an X-containing moiety. 1 and the second ring part of N, and Ar3 The third ring portion; the electron acceptor portion (A) represented by EWG; and the connector (π) containing Cy, through which the electron donor portion and the electron acceptor portion are connected.

[0197] In the electron donor portion, the first ring portion contains nitrogen (N) and L, and the portion contains nitrogen (N) and X. 1 The second ring section, and Ar 3 The third ring portion forms a fused ring, thereby suppressing the free rotation of the compound and achieving a high or increased hyperpolarizability (βzzz) and therefore a high electro-optic coefficient (r). 33 This improves the performance of optical modulators and / or optical devices comprising compounds represented by Formula 1 (e.g., in the active layer of an optical modulator, in nonlinear optical active organic materials, or any combination thereof), thereby enabling faster realization of optical transmission-based information communication and networks including such devices. Furthermore, the compound exhibits improved molecular structural stability to enhance its thermal stability, thereby improving the reliability of optical modulators and / or optical devices comprising the compound during manufacturing and use (e.g., in the active layer of an optical modulator, in nonlinear optical active organic materials, or any combination thereof). Additionally, since the optical modulator includes the compound, device manufacturing costs can be reduced.

[0198] Ar in the first ring section 1 and Ar 2 Each can be an independently substituted or unsubstituted C6 to C30 aromatic group, a substituted or unsubstituted C3 to C30 heteroaromatic group, or a fused ring group thereof. A fused ring group refers to a ring in which two or more aromatic and heteroaromatic groups are fused together.

[0199] The third ring part Ar 3 The aromatic group is a substituted or unsubstituted C6 to C30 aromatic group, a substituted or unsubstituted C3 to C30 heteroaromatic group, or any combination thereof, and the combination may be two or more fused ring groups of the aromatic group and heteroaromatic group fused together, or two or more ring groups of the aromatic group and heteroaromatic group connected by a single bond or methylene group.

[0200] The Cy-containing linker acts as a bridge between the electron donor and electron acceptor portions, and the wavelength range of absorbed light can be controlled by adjusting the conjugation length of the compound. In an exemplary embodiment, the Cy-containing linker may be a portion having a ring structure with a conjugated structure.

[0201] In the Cy-containing linker of chemical formula 1, x can be an integer from 0 to 5, for example 1 to 4; y can be an integer from 1 to 5, for example 1 to 4; z can be an integer from 0 to 5, for example 1 to 4; and n can be an integer from 1 to 5, for example 1 to 4.

[0202] In a linker containing Cy of Formula 1, when y is 2 or greater, Cy may be the same or different from each other. For example, Cy may be a part selected from Group 3, and a linker containing Cy may include two or more identical or different parts selected from Group 3.

[0203] In a linker containing Cy of Formula 1, when n is 2 or greater, Cy may be the same or different from each other. For example, Cy may be a part selected from Group 3, and a linker containing Cy may include two or more identical or different parts selected from Group 3.

[0204] Compounds of chemical formula 1 can be compounds represented by chemical formula 2.

[0205] [Chemical Formula 2]

[0206]

[0207] In chemical formula 2,

[0208] Cy, R 1 To R 4 EWG, x, y, z, and n are the same as in chemical formula 1, and

[0209] EDG is the electron donor portion represented by the chemical formula 2A:

[0210] [Chemical Formula 2A]

[0211]

[0212] In chemical formula 2 and chemical formula 2A, X 1 L, Cy, Ar 3 R 1 To R 4 EWG, x, y, z, and n can be the same as in chemical formula 1, and Y 1 To Y 7 Each can be N or CR independently. k , where R k It is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C1 to C10 alkoxy, or adjacent R kThey can be linked together to form substituted or unsubstituted C6 to C30 aromatic groups, substituted or unsubstituted C3 to C30 heteroaromatic groups, or fused rings thereof, and the * in Formula 2A indicates an atom adjacent to Formula 2 (e.g., an atom adjacent to Formula 2, a (C(R) atom adjacent to Formula 2). 1 )=C(R 2 )) x Or (Cy) y Connection points of groups, etc.

[0213] In chemical formula 2, when EDG is the electron donor portion represented by chemical formula 2A, chemical formula 2 can be represented by chemical formula 2'.

[0214] [Chemical Formula 2']

[0215]

[0216] In some exemplary embodiments, chemical formula 2 may be interchangeably represented, labeled, and / or referred to as "chemical formula 2'". As shown, chemical formula 2' may include chemical formula 2 and chemical formula 2A, such that chemical formula 2 and chemical formula 2A together constitute chemical formula 2'. As mentioned herein, the "connection point" to a chemical formula or a portion thereof may be interchangeably referred to as a connection site, bonding site, bonding point, connection portion, or bonding portion, or any combination thereof, connected to a chemical formula or a portion thereof.

[0217] In some exemplary embodiments, the Y of chemical formula 2A and / or chemical formula 2' 1 Y 2 Y 5 and Y 6 Each can be independently designated as a CR k , where R k It can be an amino group (-NR'R'', where R' and R'' are the same or different from each other, and are hydrogen atoms, C1 to C20 alkyl or C6 to C30 aryl).

[0218] In some exemplary embodiments, in chemical formula 2A and / or chemical formula 2', Y 4 Can be N or CR k (where R) k It can be halogen, cyano, C1 to C10 haloalkyl, C1 to C10 cyanoalkyl, or amino). In this case, it exists in Y. 4 Functional groups in, present in those containing L or X 1 N and Ar in the ring 3 It can increase intramolecular interactions, thereby inhibiting the free rotation of molecules and enhancing hyperpolarizability.

[0219] In some exemplary embodiments, in chemical formula 2A and / or chemical formula 2', Y7 Can be N or CR k (where R) k It can be halogen, cyano, C1 to C10 haloalkyl, C1 to C10 cyanoalkyl, or amino), and X 1 It can be -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1 -、-C(R m )=C(R n - or -C(R) p ) = N - (where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each can be independently a halogen, a C1 to C20 haloalkyl, or a C1 to C20 cyanoalkyl), and wherein -(CR f R g ) n1 In the - case, n1 can be 1 or 2. In this case, Y 7 and X 1 Hyperpolarizability can be enhanced by increasing intramolecular interactions and suppressing free rotation of molecules.

[0220] In chemical formula 2A and / or chemical formula 2', when Y 1 To Y 7 The two adjacent ones are CR k At that time, two adjacent CRs k They can connect to each other to form fused rings.

[0221] In this case, the electron donor portion EDG, represented by chemical formula 2A in chemical formula 2, can be represented by chemical formula 2AA.

[0222] [Chemical Formula 2A]

[0223]

[0224] [Chemical formula 2AA]

[0225]

[0226] In the chemical formula 2AA,

[0227] X 1 L, Y 1 To Y 7 And Ar 3 Same as in chemical formula 2A and / or chemical formula 2 or 2',

[0228] X 11 With X in chemical formula 1 1 Same, and

[0229] * indicates atoms adjacent to chemical formula 2 and / or chemical formula 2' (e.g., atoms adjacent to chemical formula 2 and / or chemical formula 2', or atoms adjacent to chemical formula 2 and / or 2'). 1 )=C(R 2 )) x Or (Cy) y Connection points of groups, etc.

[0230] In the chemical formula 2AA, one or more hydrogen atoms in each ring may optionally be replaced by at least one substituent selected from the following: deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, and substituted or unsubstituted C6 to C20 aryloxy.

[0231] In the chemical formula 2AA, the CH of the aromatic ring can be replaced by N, and an aromatic ring may include one or more (e.g., 1, 2, or 3) N.

[0232] In chemical formulas 1 and 2, X 1 And L; X in group 1 a and X b The Ar described below 3 X 21 and X 23 X of chemical formula 2AA 11 ; and R in group 3 b and R c In the middle, a ring structure (e.g., may be included in X) 1The "first ring structure" in L, and the "second ring structure" that may be included in L, can each be independently a spirocyclic structure or a fused ring structure. The spirocyclic structure can be a substituted or unsubstituted C3 to C30 (e.g., C5 to C30) hydrocarbon ring group or a substituted or unsubstituted C2 to C30 heterocyclic group. The substituted or unsubstituted C3 to C30 (e.g., C5 to C30) hydrocarbon ring group can be, for example, a substituted or unsubstituted C3 to C30 (e.g., C5 to C30) cycloalkyl group (e.g., a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C5 to C20 cycloalkyl group, or a substituted or unsubstituted C5 to C10 cycloalkyl group), a substituted or unsubstituted C6 to C30 aryl group (e.g., a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C6 to C20 aryl group), or a substituted or unsubstituted C6 to C30 aryl group. The fused ring consists of unsubstituted C6-C10 aryl groups, or substituted or unsubstituted C3-C30 (e.g., C5-C30) cycloalkyl groups (e.g., substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C5-C20 cycloalkyl, or substituted or unsubstituted C5-C10 cycloalkyl) and substituted or unsubstituted C6-C30 aryl groups (e.g., substituted or unsubstituted C6-C20 aryl or substituted or unsubstituted C6-C10 aryl). Examples of fused rings include fluorenyl, indaminozyl, etc. The substituted or unsubstituted C2-C30 heterocyclic group may be, for example, a substituted or unsubstituted C2-C30 heterocyclic alkyl group (e.g., substituted or unsubstituted C2-C20 heterocyclic alkyl or substituted or unsubstituted C2-C10 heterocyclic alkyl).

[0233] The fused ring structure can be a fused substituted or unsubstituted C3 to C30 (e.g., C5 to C30) hydrocarbon ring group, a fused substituted or unsubstituted C2 to C30 heterocyclic group, or a fused ring thereof. The substituted or unsubstituted C3 to C30 (e.g., C5 to C30) hydrocarbon ring group can be, for example, a substituted or unsubstituted C3 to C30 (e.g., C5 to C30) cycloalkyl group (e.g., a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C5 to C20 cycloalkyl group, or a substituted or unsubstituted C5 to C10 cycloalkyl group) or a substituted or unsubstituted C6 to C30 aryl group (e.g., a substituted or unsubstituted C6...). The C2 to C30 heterocyclic group can be, for example, a substituted or unsubstituted C2 to C30 heterocyclic alkyl group (e.g., a substituted or unsubstituted C2 to C20 heterocyclic alkyl group or a substituted or unsubstituted C2 to C10 heterocyclic alkyl group) or a substituted or unsubstituted C2 to C30 heteroaryl group (e.g., a substituted or unsubstituted C2 to C20 heteroaryl group or a substituted or unsubstituted C2 to C10 heteroaryl group).

[0234] The helical structure may include one of the multiple parts represented by group 1 (e.g., one of parts (1) to (9) in group 1).

[0235] [Group 1]

[0236]

[0237] In group 1,

[0238] X a and X b They can be independently -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、or-GeR dd R ee - (where R) a1 R a2 R b R c R d and R e Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy, and R bb R cc R dd and R ee Each can be independently (CH2) z Alternatively, heteroatoms such as O, N, S, Se, or Te may be present, where (CH2) z In this context, z is a positive integer (e.g., a positive integer from 1 to 5, or from 2 to 3), and R is a positive integer. bb and R cc The pair or R dd and R ee The pairs can be connected to each other to form a fourth ring structure, which can also be referred to interchangeably as the "third ring structure" in this article, etc.

[0239] L a Can be -O-, -S-, -Se-, -Te-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CRf R g ) n1 -、-C(R p ) = N-, or single bond (where R a1 R a2 R b R c R d R e R f R g and R p Each of these can be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy), wherein -(CR f R g ) n1 In - n1 is 1 or 2, and

[0240] One or more hydrogens in each ring may optionally be replaced by at least one substituent selected from: deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, and substituted or unsubstituted C6 to C20 aryloxy.

[0241] In group 1, one or more CHs present in the aromatic rings of parts (3), (4), (5), (6) and (7) can be replaced by N.

[0242] In chemical formula 1, Ar 3 It can be any of the multiple parts represented by group 2 (e.g., one of parts (1) to (9) in group 2).

[0243] [Group 2]

[0244]

[0245] In group 2,

[0246] X 21 and X 23 They can each independently be single bonds, -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee-、-CR f R g - or -CR ff R gg - (where R) a1 R a2 R b R c R d R e R f and R g Each of these can be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy, and R bb R cc R dd R ee R ff and R gg Each can be independently (CH2) w Alternatively, heteroatoms such as O, N, S, Se, or Te may be present, where (CH2) w In this context, w is a positive integer (e.g., a positive integer from 1 to 5, or from 2 to 3), and R is a positive integer. bb and R cc The pair, R dd and R ee The pair, or R ff and R gg The pairs can be connected to each other to form a fifth ring structure (which can also be referred to interchangeably as the "third ring structure" in this article).

[0247] R 21 It can be hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, substituted or unsubstituted C2 to C30 acyl, halogen, cyano (-CN), cyano-containing group, nitro, pentafluorothioalkyl (-SF5), hydroxyl, amino, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphate or its salt, -SiR a R b R c (where R) a R b and R c Each of the following is independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, or any combination thereof.

[0248] Y 21 To Y 28 Each can be N or CR independently. k , where R kIt is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C1 to C10 alkoxy, or adjacent R k They can be linked together to form substituted or unsubstituted C6 to C30 aromatic groups, substituted or unsubstituted C3 to C30 heteroaromatic groups, or fused rings thereof, provided that, in group 2, part (4) of Y 21 To Y 24 Y in any one of the parts (5) 25 To Y 28 Y in any one of the parts (6) 25 To Y 28 Y in any one or part of (7) 25 To Y 28 Any of them can be a group that connects a single bond, more precisely, the group adjacent to the (C(R) group in formula 1. 1 )=C(R 2 )) x Or (Cy) y Groups linked by groups,

[0249] *=* represents the presence of X in chemical formula 1. 1 The ring-fused portion, and

[0250] -* indicates the (C(R) adjacent to chemical formula 1. 1 )=C(R 2 )) x Or (Cy) y Connection points of functional groups.

[0251] In group 2, the hyperpolarizability of the compound can be improved when two or more monocyclic rings of the conjugated structure are fused as in (2), (3) and (5) to (9).

[0252] In chemical formula 1, Cy can be any of the multiple parts represented by group 3 (e.g., one of the parts (1) to (17) of group 3).

[0253] [Group 3]

[0254]

[0255] In group 3,

[0256] Z 11 Z 12 and Z 13 Each can be independently represented as O, S, Se, Te, S(=O), S(=O)2, NR a or SiR b R c (where R) a Rb and R c Each of these can be independently hydrogen, C1 to C10 alkyl, C1 to C10 haloalkyl, -SiH3, C1 to C10 alkylsilyl, -NH2, C1 to C10 alkylamino, C6 to C12 aryl, C3 to C12 heteroaryl, halogen, cyano, or any combination thereof.

[0257] Z 20 and Z 21 Each can be independently O, S, Se, or Te.

[0258] R b and R c They can exist independently or be connected to form a sixth ring structure (which can also be interchangeably referred to as the "third ring structure," etc.), and

[0259] * indicates the connection point with chemical formula 1.

[0260] One or more hydrogens in the ring structure of each part of Group 3 may be unsubstituted or substituted, and when substituted, they may be replaced by, for example, C1 to C10 alkyl, C1 to C10 alkoxy, C1 to C10 haloalkyl, -SiH3, C1 to C10 alkylsilyl, -NH2, C1 to C10 alkylamino, C6 to C12 aryl, C3 to C12 heteroaryl, halogen, or cyano.

[0261] In chemical formula 1, EWG can be a cyclic group represented by chemical formula 3.

[0262] [Chemical Formula 3]

[0263]

[0264] In chemical formula 3,

[0265] EWG' is a substituted or unsubstituted C6 to C30 (e.g., C6 to C20 or C6 to C10) aryl, a substituted or unsubstituted C3 to C30 (e.g., C3 to C20 or C3 to C10) heteroaryl, or a substituted or unsubstituted C3 to C30 (e.g., C3 to C20 or C3 to C10) heterocyclic alkenyl.

[0266] Z can be O, S, Se, Te, or CR a R b , where R a and R b Each is independently a cyano group or a cyano-containing group, and

[0267] *This can be a connection point with chemical formula 1.

[0268] In chemical formula 1, EWG can be any cyclic group represented by chemical formula 3A to chemical formula 3G.

[0269] [Chemical Formula 3A]

[0270]

[0271] In chemical formula 3A,

[0272] Z 1 For O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group.

[0273] Z 2 For O, S, Se, Te, or CR a R b , where R a and R b Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group.

[0274] Z 3 For N or CR c (where R) c (It is hydrogen, deuterium, or substituted or unsubstituted C1 to C10 alkyl groups),

[0275] R 11 R 12 R 13 R 14 and R 15 It may be the same or different and may be independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl (e.g., C1 to C30 (C1 to C20 or C1 to C10) haloalkyl), substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), cyano-containing group, or any combination thereof, wherein R 12 and R 13 and R 14 and R 15 They can exist independently or connect with each other to form dense aromatic rings.

[0276] n is 0 or 1, and

[0277] * indicates a bonding location (e.g., the connection point with chemical formula 1).

[0278] [Chemical Formula 3B]

[0279]

[0280] In the chemical formula 3B,

[0281] Z 1 For O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group.

[0282] Z 2 For O, S, Se, Te, or CR a R b , where R a and R b Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group.

[0283] Z 3 For O, S, Se, Te, or C(R) a (CN) (where R) a It can be hydrogen, cyano (-CN), or C1 to C10 alkyl.

[0284] R 11 and R 12 Each of the following is independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl (e.g., C1 to C30 (C1 to C20 or C1 to C10) haloalkyl), substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), or any combination thereof, and

[0285] * indicates a bonding location (e.g., the connection point with chemical formula 1).

[0286] [Chemical formula 3C]

[0287]

[0288] In the chemical formula 3C,

[0289] Z 1 For O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group.

[0290] Z 2 For O, S, Se, Te, or CR a R b , where R a and R b Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group.

[0291] R 11 R 12 and R 13 The same or different and each independently being hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl (e.g., C1 to C30 (C1 to C20 or C1 to C10) haloalkyl), substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), or any combination thereof, and

[0292] * indicates a bonding location (e.g., the connection point with chemical formula 1).

[0293] [Chemical Formula 3D]

[0294]

[0295] In chemical formula 3D,

[0296] Z 1 For O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group.

[0297] Z 2 For O, S, Se, Te, or CR a R b , where R a and R b Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group.

[0298] Z 3 For N or CR c (where R) c (Hydrogen or substituted or unsubstituted C1 to C10 alkyl groups),

[0299] G 1 For O, S, Se, Te, SiR x R y , or GeR z R w , where R x R y R z and R w They may be the same or different and are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, or substituted or unsubstituted C6 to C20 aryl.

[0300] R 11 R12 and R 13 The same or different and each independently being hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl (e.g., C1 to C30 (C1 to C20 or C1 to C10) haloalkyl), substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano, cyano-containing group, or any combination thereof, wherein R 12 and R 13 They can exist independently or connect with each other to form dense aromatic rings.

[0301] n is 0 or 1, and

[0302] * indicates a bonding location (e.g., the connection point with chemical formula 1).

[0303] [Chemical formula 3E]

[0304]

[0305] In the chemical formula 3E,

[0306] Z 1 For O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group.

[0307] Z 2 For O, S, Se, Te, or CR a R b , where R a and R b Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group.

[0308] Z 3 For N or CR c (where R) c (Hydrogen or substituted or unsubstituted C1 to C10 alkyl groups),

[0309] G 2 For O, S, Se, Te, SiR x R y , or GeR z R w , where R x R y R z and R wThey may be the same or different and are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, or substituted or unsubstituted C6 to C20 aryl.

[0310] R 11 R 12 and R 13 The same or different and each independently being hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl (e.g., C1 to C30 (C1 to C20 or C1 to C10) haloalkyl), substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano, cyano-containing group, or any combination thereof.

[0311] n is 0 or 1, and

[0312] * indicates a bonding location (e.g., the connection point with chemical formula 1).

[0313] [Chemical formula 3F]

[0314]

[0315] In the chemical formula 3F,

[0316] Z 1 For O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group.

[0317] Z 2 For O, S, Se, Te, or CR a R b , where R a and R b Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group.

[0318] R 11 It can be hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl (e.g., C1 to C30 (C1 to C20 or C1 to C10) haloalkyl), substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), cyano-containing groups, or any combination thereof.

[0319] G 3 For O, S, Se, Te, SiR x R y , or GeR z R w , where Rx R y R z and R w The same or different and each independently being hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, or substituted or unsubstituted C6 to C20 aryl, and

[0320] * indicates a bonding location (e.g., the connection point with chemical formula 1).

[0321] [Chemical formula 3G]

[0322]

[0323] In the chemical formula 3G,

[0324] Z 1 For O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group.

[0325] R 11 To R 13 It can be hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl (e.g., C1 to C30 (C1 to C20 or C1 to C10) haloalkyl), substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), cyano-containing groups, or any combination thereof.

[0326] G 3 For O, S, Se, Te, SiR x R y , or GeR z R w , where R x R y R z and R w The same or different and each independently being hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, or substituted or unsubstituted C6 to C20 aryl, and

[0327] * indicates a bonding position (e.g., the connection point with chemical formula 1).

[0328] In chemical formulas 3A to 3G, the substituted or unsubstituted C1 to C30 alkyl group may be a C1 to C30 (or C1 to C20) haloalkyl group, such as a C1 to C30 (or C1 to C20) fluoroalkyl group.

[0329] Examples of compounds represented by chemical formula 1 may include any of the compounds in group 4.

[0330] [Group 4]

[0331] [1-1] [1-2] [1-3] [1-4]

[0332]

[0333] [1-5] [1-6] [1-7] [1-8]

[0334]

[0335] [1-9] [1-10] [1-11] [1-12]

[0336]

[0337] [1-13] [1-14] [1-15]

[0338]

[0339] [1-16] [1-17]

[0340]

[0341] [1-18] [1-19] [1-20]

[0342]

[0343] [1-21] [1-22]

[0344]

[0345] In group 4, TBDPS is the oxygen protecting group of tert-butyldiphenylsilyl, and Ph is phenyl.

[0346] Compounds represented by chemical formula 1 (e.g., compounds listed in group 4) can be synthesized by methods known in the art, with reference to, but not limited to, the methods described in synthesis examples 1 to 17 below.

[0347] As described above, the compound represented by Formula 1 has a structure in which the first ring moiety, the second ring moiety, and the third ring moiety are fused together, thereby suppressing the free rotation of the compound and achieving a high hyperpolarizability (βzzz), thus obtaining a high or increased electro-optic coefficient (r). 33 The electro-optic coefficient refers to the degree to which the refractive index (e.g., the refractive index of a compound or an optical modulator and / or device comprising it) changes when an electric field is applied from the outside (e.g., externally to the compound, optical modulator, device, etc.), and a high electro-optic coefficient means that the performance of the device (e.g., an optical modulator, an optical device comprising it, etc.) can be improved based on (e.g., in the active layer of the optical modulator, in a nonlinear optically active organic material, or any combination thereof) including a compound represented by chemical formula 1.

[0348] The relationship between hyperpolarizability and electro-optic coefficient is represented by equations 1 to 3.

[0349] [Relational Equation 1]

[0350]

[0351] In equation 1, n' is the refractive index after the electric field is applied, n is the refractive index before the electric field is applied, Δn is the change in refractive index, and r 33 It is the electro-optic coefficient, and E is the electric field strength.

[0352] [Relational Equation 2]

[0353]

[0354] In relational equation 2, r 33 It is the electro-optic coefficient. It is a second-order nonlinear susceptibility caused by the interaction of two light waves at frequency ω with a static (zero-frequency) field, and It is based on the change in refractive index of the electric field strength E.

[0355] [Relationship Equation 3]

[0356]

[0357] In relational equation 3 It is the second-order nonlinear polarizability caused by the interaction of two light waves at frequency ω with a static (zero-frequency) field, where N is the molecular density of the compound, and β... zzz It is the hyperpolarizability, and θ is the orientation angle of the molecule. In equation 3, It represents the degree of orientation, which indicates the degree of orientation of the chromophore through the polarization process.

[0358] Hyperpolarizability and orientation play important roles in determining the electro-optic coefficient.

[0359] The compound may have a hyperpolarizability of less than or equal to about -170, for example less than or equal to about -200, less than or equal to about -300, less than or equal to about -400, or less than or equal to about -500. There is no particular limitation on the lower limit of the hyperpolarizability, but it may be approximately greater than or equal to about -2500, for example greater than or equal to about -2100, or greater than or equal to about -1500. The hyperpolarizability can be calculated using the DFT(B3LYP, M062X) program.

[0360] The compound may have a dipole moment greater than or equal to about 11 Debyes, for example, greater than or equal to about 14 Debyes, greater than or equal to about 15 Debyes, greater than or equal to about 16 Debyes, or greater than or equal to about 17 Debyes, and may have a dipole moment less than or equal to about 30 Debyes, less than or equal to about 29 Debyes, less than or equal to about 28 Debyes, less than or equal to about 27 Debyes, less than or equal to about 26 Debyes, or less than or equal to about 25 Debyes. The dipole moment can be calculated using the DFT(B3LYP, M062X) program.

[0361] The glass transition temperature of the compound may be less than or equal to about 150°C, for example, greater than or equal to about 85°C and less than or equal to about 150°C, greater than or equal to about 90°C and less than or equal to about 150°C, greater than or equal to about 91°C and less than or equal to about 130°C, or greater than or equal to about 91.8°C and less than or equal to about 110°C. The glass transition temperature can be measured by DTA (differential thermal analysis).

[0362] The compound can be formed into a film by dry processes such as polarization processes and inexpensive solution processes such as spin coating, inkjet printing or spraying.

[0363] Polarization processes can be methods for forming films by heating a compound while applying an electric field.

[0364] Solution processing may include coating processes that prepare coating compositions by adding the compound to a solvent, and the solvents used may include ether-based solvents (e.g., tetrahydrofuran (THF), diethyl ether, 1,2-dimethoxyethane (DME), cyclopentylmethyl ether (CPME), etc.), halocarbon solvents (e.g., dichloromethane, dibromomethane, chloroform, 1,2-dichloroethane, 1,2-dibromoethane, etc.), and amide-based solvents (e.g., N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrole). Solvents include ketones (NMP, etc.), ketone-based solvents (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, etc.), alcohol-based solvents (e.g., methanol, ethanol, 2-propanol, n-propanol, etc.), aliphatic hydrocarbon solvents (e.g., n-heptane, n-hexane, cyclohexane, etc.), aromatic hydrocarbon solvents (e.g., benzene, toluene, xylene, ethylbenzene, etc.), halogenated aromatic hydrocarbon solvents (e.g., chlorobenzene, dichlorobenzene, etc.), glycol ether-based solvents (e.g., ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, etc.), or glycol-based solvents (e.g., ethylene glycol, propylene glycol, etc.). These solvents can be used alone or in combination of two or more.

[0365] In the above solution process, based on 100% by weight of the coating composition, the compound may be included in an amount of about 1% to about 20% by weight, for example, about 5% to about 15% by weight.

[0366] The compound has a high or increased electro-optic coefficient and is therefore usable as a nonlinear optical chromophore in an optical modulator, thereby enabling the optical modulator to exhibit improved performance and enabling high-speed information communication via optical transmission (e.g., manufacturing devices that support such communication at a reduced manufacturing cost).

[0367] Examples of optical modulators mentioned above include electro-optic modulators and silicon-organic hybrid modulators.

[0368] Electro-optic modulators convert electrical signals into light intensity signals by using the electro-optic effect to convert the absorbance or refractive index of light.

[0369] The following will refer to Figure 1 and 2 Describe an optical modulator.

[0370] Figure 1 This is a schematic diagram illustrating the usage of an optical modulator in an optical communication device, such as a Mach-Zehnder interferometer, according to some exemplary embodiments. Figure 2 This is a cross-sectional view of an optical modulator according to some exemplary embodiments.

[0371] Reference Figure 1The optical modulator 100 is disposed in an optical communication device (“optical device”) such as a Mach-Zehnder interferometer 2, but the exemplary embodiments are not limited thereto. The Mach-Zehnder interferometer 2 is equipped with (for example, including) an input section 3, a branch section 4, a first branch waveguide 5, a second branch waveguide 6, a combination section 7, and an output section 8, and the optical modulator 100 is disposed in the first branch waveguide 5.

[0372] The optical modulator 100 includes an incident unit 10 (also referred to as an incident terminal, incident port, input terminal, or input port), an output unit 11 (also referred to as an output terminal or output port), an optical waveguide 12 connecting the incident unit 10 to the output unit 11 (e.g., between the incident unit 10 and the output unit 11), and an input electrode 13 for modulating an electrical input signal (e.g., from the power supply of an electronic device, such as...). Figure 3 The power supply 950 of the electronic device 900 shown is input to the input electrode 13. When light passes through the optical waveguide 12, the optical modulator 100 outputs (e.g., transmits) an optically modulated signal modulated by the modulation electrical input signal input (e.g., transmitted) to the output unit 11.

[0373] Light incident on input section 3 branches at branch section 4 into first branch waveguide 5 and second branch waveguide 6. A portion of the light branching into first branch waveguide 5 is incident on optical modulator 100 (e.g., at its incident unit 10) and emitted from optical modulator 100 as an optically modulated signal modulated by a modulation electrical input signal input to input electrode 13. The optically modulated signal is combined with another portion of the light propagating through second branch waveguide 6 in combination section 7 and output (transmitted) from output section 8 as a modulated optical output signal with a specific (or alternatively, predetermined) modulation intensity applied.

[0374] Reference Figure 2According to some exemplary embodiments, the optical modulator 100 includes a first electrode 14, a second electrode 30 facing the first electrode 14, and an active layer 20 between the first electrode 14 and the second electrode 30 (e.g., directly or indirectly between the first electrode 14 and the second electrode 30). The first electrode 14 may be made of (e.g., may include at least partially or completely) a metal such as Au, Mg, or Al; alloys thereof; a conductive metal oxide such as zinc oxide, indium oxide, tin oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or fluorine-doped tin oxide; or any combination of metals and oxides, such as ZnO and Al or SnO2 and Sb, but is not limited thereto. The second electrode 30 may be made of the same material as the first electrode 14 or a different material. In some exemplary embodiments, the first electrode 14 may include a metal oxide such as ITO or IZO, and the second electrode 30 may include a metal such as Au, Mg, or Al. The active layer 20 includes compounds described above (e.g., compounds represented by chemical formula 1) as nonlinear optically active organic materials.

[0375] Although not in Figure 2 As shown, however, a substrate may be present beneath the first electrode 14 (e.g., such that the first electrode 14 is between the active layer 20 and the substrate (e.g., directly or indirectly between the active layer 20 and the substrate)). The substrate may be made of (e.g., may include at least partially or completely the following): inorganic materials such as glass; organic materials such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, polyamide, polyethersulfone, or any combination thereof; or a silicon wafer. The substrate may be omitted.

[0376] The optical modulator 100 may further include a charge-blocking layer between the first electrode 14 and the active layer 20 (e.g., directly or indirectly between the first electrode 14 and the active layer 20). The charge-blocking layer may further include inorganic oxides such as Al2O3, ZrO2, SiO2, TiO2, SnO2, CeO2, MgO, NiO, CaO, Ga2O3, ZnO, HfO2, and any combination thereof.

[0377] The charge blocking layer may have a thickness of about 30 nm to about 150 nm, for example about 40 nm to about 120 nm.

[0378] In addition to the compound represented by Formula 1, the active layer 20 may further include a matrix polymer, a photoconductive polymer, a photosensitizer, or any combination thereof.

[0379] Matrix polymers can provide good dispersion of nonlinear optically active organic materials (compounds of Formula 1), maintain polarized orientation, and provide mechanical and thermal stability. Examples of matrix polymers may include, but are not limited to, poly(C1 to C10) alkyl acrylates such as polymethacrylate, poly(C1 to C10) alkyl methacrylates such as polymethyl methacrylate, polycarbonate (PC), polyimide (PI), polyurethane (PU), epoxy-based polymers, polysiloxane-based polymers, polystyrene (PS), polyvinyl alcohol (PVA), and polyvinyl chloride (PVC).

[0380] Photoconductive polymers may include, for example, carbazole units or triphenylamine units, but are not limited thereto. Photoconductive polymers may include, for example, polyvinylcarbazole (PVK), polysiloxane carbazole, poly(p-phenylenevinylene), polyaniline, polypyrrole, polyacetylene, polythiophene, polyalkylthiophene, carbazole-substituted polysiloxane (PSX-Cz), poly(p-phenylene terephthalate)carbazole (PPT-CZ), poly(meth)acrylate triphenylamine (TATPD), derivatives thereof, mixtures thereof, or copolymers thereof.

[0381] Photosensitizers can be excited by a light source of a specific wavelength (e.g., visible light) to generate electrons and holes. Photosensitizers may include, for example, C60 fullerene, PCBM (methyl phenyl-C61-butyrate), TNF (2,4,7-trinitrofluorenone), TNFDM (2,4,7-trinitro-9-fluorene-malononitrile), or any combination thereof.

[0382] The thickness of the active layer 20 can range from about 100 nm to 1500 nm. The active layer 20 can be formed as a single layer or as a multilayer of two or more layers.

[0383] Besides Mach-Zehnder interferometers, optical modulators can be used in a variety of other optical devices. These devices include 3D imaging systems, 3D cameras, laser detection and ranging (LiDAR) devices, phased array antennas, and more.

[0384] Figure 3 This is a schematic diagram of an electronic device 900 according to some example implementations.

[0385] refer to Figure 3Electronic device 900 may include a processor 920 (e.g., a central processing unit or CPU), a memory 930 (e.g., a solid-state drive (SSD) storage device), an auxiliary device 940, and a power supply 950, all electrically connected to each other via a bus 910. The auxiliary device 940 may include an optical device comprising an optical modulator 100. The optical device may be an optical device including an optical modulator 100 according to any embodiment, such as the Mach-Zehnder interferometer 2 described above. The memory 930 (and / or the memory of the auxiliary device 940) may be a non-transitory computer-readable medium (e.g., an SSD storage device) and may store instructions. The processor 920, such as a CPU, may execute the stored instructions to perform one or more functions. The power supply 950 may include a rechargeable battery, such as a lithium-ion battery.

[0386] Processor 920 (and / or the processor of auxiliary device 940) may be configured to adjustably control the voltage of power (e.g., power supplied from power supply 950) applied to one or more components of the optical device and / or optical modulator of auxiliary device 940. For example, processor 920 may be configured to adjustably control the voltage of the modulated electrical input signal to optical modulator 100 (e.g., as...). Figure 1 The supply of input electrodes 13 to the Mach-Zehnder interferometer 2 shown is used to control the optical modulation signal output (transmitted) (e.g., transmitted to output unit 11) by the optical modulator 100. The auxiliary device 940 may include a communication interface (e.g., an optical communication interface) configured to transmit the optical modulation signal to an external device to enable optical transmission and thus communication based thereon.

[0387] Processor 920 may be configured to generate output (e.g., to cause a modulated electrical input signal to be transmitted to the input electrode 13 of optical modulator 100) based on processing instructions stored in memory 930. In some embodiments, auxiliary device 940 may be electrically connected to power supply 950 independently of bus 910, and the processor and / or power supply 950 included in auxiliary device 940 may be configured to adjustably control the application of the modulated electrical input signal to optical modulator 100 (e.g., its input electrode 13) and / or optical device (e.g., interferometer 2) including it based on power supplied from power supply 950. In some embodiments, one or more of bus 910, processor 920, memory 930, and / or power supply 950 may be omitted.

[0388] Electronic device 900 and / or any part thereof (e.g., processor 920, memory 930, auxiliary device 940, power supply 950, etc.) may include a processing circuitry system, such as hardware including logic circuitry; a hardware / software combination such as software implemented by a processor; or any combination thereof. For example, the processing circuitry system may be a central processing unit (CPU), an arithmetic logic unit (ALU), a digital signal processor, a microcomputer (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. As an example, the processing circuitry system may include a non-transitory computer-readable storage device. Processor 920 (e.g., a central processing unit or CPU) may, for example, control the operation of auxiliary device 940 (e.g., its optical modulator 100, optical devices including it, etc.) by executing a program of instructions stored in memory 930 (e.g., a solid-state drive (SSD) storage device).

[0389] In the following description, some exemplary implementations are illustrated in more detail with reference to embodiments. However, the following embodiments are for illustrative purposes only and are not intended to limit the scope.

[0390] Synthesis Example 1: Synthesis of a compound represented by chemical formula 1-1

[0391] [Chemical Formula 1-1]

[0392]

[0393] (1) Synthesis of compound 1-1b

[0394] 2.0 g (6.5 mmol) of compound 1-1a and 3.5 g (7.9 mmol) of triphenyl(2-thienylmethyl) bromide were used in 40 ml of tetrahydrofuran (THF). (CAS No. 23259-98-5) A suspension was prepared by adding 0.6 g (60 wt%, 15.6 mmol) of NaH to it. After stirring the mixture at room temperature for one day, the reaction temperature was raised to 40 °C and stirred for several more hours. Then, purification was carried out by silica gel column chromatography (using hexane and ethyl acetate as eluents) to obtain 2.4 g (6.0 mmol) of compound 1-1b (yield: 92.5%).

[0395] [Compound 1-1a]

[0396]

[0397] [Compound 1-1b]

[0398]

[0399] (2) Synthesis of compound 1-1c

[0400] A solution was prepared using 2.2 g (5.6 mmol) of compound 1-1b with 300 mL of chloroform, and 7.7 mL (23.3 mmol) of a reagent for the Vilsmeier-Haack reaction (prepared in advance with DMF and POCl3) was added to it at 0 °C. After the addition was complete, the mixture was stirred while the temperature was raised to room temperature. Purification was then performed by silica gel column chromatography (using hexane and ethyl acetate as eluents) to obtain 1.6 g (3.8 mmol) of compound 1-1c (yield: 69.1%).

[0401] [Compound 1-1c]

[0402]

[0403] (3) Synthesis of compounds represented by chemical formula 1-1

[0404] A suspension was prepared by using 1.6 g (3.8 mmol) of compound 1-1c and 1.1 g (3.4 mmol) of 2-[3-cyano-4-methyl-5-phenyl-5-(trifluoromethyl)furan-2(5H)-ylidene]malonitrile (CAS No. 436097-14-2) with a mixed solvent of 17 ml toluene and 17 ml ethanol, and then stirred at 55 °C for one day. Purification was then performed by silica gel column chromatography (using hexane, chloroform, and acetone as eluents) to obtain 2.1 g (2.9 mmol) of the compound represented by formula 1-1 (yield: 97.8%).

[0405] 1 H NMR (500 MHz, CD2Cl2): δ 1.77 (s, 6H), 6.75 (d, 1H), 7.16 (d, 1H), 7.25 (d, 2H), 7.35-7.40 (m, 3H), 7.50-7.61 (m, 8H), 7.74 (d, 1H), 7.77 (d,1H), 7.91 (d, 1H), 8.12 (d, 1H), 8.15 (t, 2H).

[0406] Synthesis Example 2: Synthesis of compounds represented by chemical formulas 1-2

[0407] [Chemical Formula 1-2]

[0408]

[0409] Compound 1-2b (yield: 99.9%) was synthesized in the same manner as in step (1) of Synthesis Example 1, except that compound 1-2a (CAS No. 3055740-49-0) was used instead of compound 1-1a.

[0410] [Compounds 1-2a]

[0411]

[0412] [Compounds 1-2b]

[0413]

[0414] Compound 1-2c was synthesized in the same manner as in step (2) of Synthesis Example 1 (yield: 99.9%), except that compound 1-2b was used instead of compound 1-1b.

[0415] [Compounds 1-2c]

[0416]

[0417] The compound represented by chemical formula 1-2 was synthesized in the same manner as in step (3) of Synthesis Example 1 (yield: 67.5%), except that compound 1-2c was used instead of compound 1-1c.

[0418] One of the two stereoisomers 1 The H NMR is as follows.

[0419] 1 H NMR (500 MHz, CD2Cl2): δ 1.65 (s, 6H), 6.06 (d, 1H), 7.06 (d, 1H), 7.31-7.84 (m, 13H), 7.80 (d, 1H), 7.83 (d, 1H), 8.01-8.04 (m, 2H).

[0420] The other of the two stereoisomers 1 The H NMR is as follows.

[0421] 1 H NMR (500 MHz, CD2Cl2): δ 1.70 (s, 6H), 6.67 (d, 1H), 6.94 (d, 1H), 7.07 (d, 1H), 7.23 (s, 1H), 7.30-7.54 (m, 11H), 7.56 (d, 1H), 7.58 (d, 1H), 7.59 (d, 1H), 7.69 (d, 1H).

[0422] Synthesis Example 3: Synthesis of compounds represented by chemical formulas 1-3

[0423] [Chemical Formulas 1-3]

[0424]

[0425] Compound 1-3b (yield: 93.3%) was synthesized in the same manner as in step (1) of Synthesis Example 1, except that 1-3a (CAS No. 2661611-43-2) was used instead of compound 1-1a.

[0426] [Compounds 1-3a]

[0427]

[0428] [Compounds 1-3b]

[0429]

[0430] Compound 1-3c was synthesized in the same manner as in step (2) of Synthesis Example 1 (yield: 99.9%), except that compound 1-3b was used instead of compound 1-1b.

[0431] [Compounds 1-3c]

[0432]

[0433] The compounds represented by chemical formulas 1-3 were synthesized in the same manner as in step (3) of Synthesis Example 1 (yield: 55.1%), except that compound 1-3c was used instead of compound 1-1c.

[0434] One of the two stereoisomers 1 The H NMR is as follows.

[0435] 1 H NMR (500 MHz, CD2Cl2): δ 1.66 (s, 6H), 5.97 (d, 1H), 7.06 (d, 1H), 7.32 (d, 1H), 7.36-7.53 (m, 10H), 7.66 (s, 1H), 7.75 (s, 1H), 7.80 (dd, 2H),8.04-8.05 (m, 2H).

[0436] The other of the two stereoisomers 1 The H NMR is as follows.

[0437] 1H NMR (500 MHz, CD2Cl2): δ 1.68 (s, 6H), 6.66 (d, 1H), 6.79 (d, 1H), 7.04 (d, 1H), 7.13-7.45 (m, 7H), 7.50-7.58 (m, 5H), 7.66-7.70 (m, 2H), 8.36 (d, 1H), 8.08 (d, 1H).

[0438] Synthesis Example 4: Synthesis of compounds represented by chemical formulas 1-4

[0439] [Chemical Formulas 1-4]

[0440]

[0441] The compounds represented by chemical formulas 1-4 (yield: 54.6%) were synthesized in the same manner as in step (3) of Synthesis Example 1, except that: compound 1-2c was used instead of compound 1-1c, 1,3-bis(dicyanomethylene)indane (CAS No. 38172-19-9) was used instead of 2-[3-cyano-4-methyl-5-phenyl-5-(trifluoromethyl)furan-2(5H)-ylidene]malonitrile (CAS No. 436097-14-2), the solvent was changed to acetic anhydride, and the reaction temperature was changed to 90°C.

[0442] 1 H NMR (500 MHz, CD2Cl2): δ 1.73 (s, 6H), 6.93 (d, 1H), 7.12 (d, 1H), 7.32 (d, 1H), 7.39-7.43 (m, 4H), 7.47 (d, 1H), 7.59 (m, 2H), 7.80 (m, 2H), 7.85 (d, 1H), 7.89 (d, 1H), 8.10 (d, 1H), 8.55-8.57 (m, 2H).

[0443] Synthesis Example 5: Synthesis of compounds represented by chemical formulas 1-5

[0444] [Chemical Formulas 1-5]

[0445]

[0446] (1) Synthesis of compounds 1-5b

[0447] A solution was prepared using 3.0 g (9.5 mmol) of compounds 1-2a from Synthesis Example 2, 1.5 mL (10.4 mmol) of isophorone (CAS No. 78-59-1), and 30 mL of EtOH. 4.2 mL (11.3 mmol) of 21% EtONa (EtOH solution) was added, and the mixture was stirred at 85 °C for 2 hours. Purification by silica gel column chromatography (using hexane and acetone as eluents) was then performed to prepare 3.8 g (8.8 mmol) of compounds 1-5b (yield: 93.2%).

[0448] [Compounds 1-5b]

[0449]

[0450] (2) Synthesis of compounds 1-5c

[0451] Subsequently, a suspension was prepared using 0.33 g (60 wt%, 8.2 mmol) NaH and 60 ml THF, then cooled to 0 °C, and 1.1 ml (7.5 mmol) diethyl (cyanomethyl)phosphonate was slowly added dropwise. After stirring the mixture for 10 min, 3.0 g (6.9 mmol) of compound 1-5b was dissolved in 3 ml THF and then added dropwise thereto. After the dropwise addition was complete, the mixture was stirred for 18 h by raising the temperature to 70 °C. Purification was then performed by silica gel column chromatography (using dichloromethane as eluent) to obtain 2.7 g (5.9 mmol) of compound 1-5c (yield: 85.5%).

[0452] [Compounds 1-5c]

[0453]

[0454] (3) Synthesis of compounds 1-5d

[0455] Subsequently, a solution was prepared using 1.0 g (2.2 mmol) of compound 1-5c and 50 mL of toluene. This solution was cooled to -78 °C, and 3.3 mL (3.3 mmol) of diisobutylaluminum hydride (1.0 M, in THF solution) was added dropwise. After stirring for 2 hours, the temperature was raised to room temperature for 1 hour. Purification was then performed by silica gel column chromatography (using hexane and dichloromethane as eluents) to obtain 0.9 g (1.9 mmol) of compound 1-5d (yield: 88.8%).

[0456] [Compounds 1-5d]

[0457]

[0458] (4) Synthesis of compounds represented by chemical formulas 1-5

[0459] Subsequently, a suspension was prepared using 0.5 g (1.0 mmol) of compounds 1-5d, 0.4 g (1.2 mmol) of 2-[3-cyano-4-methyl-5-phenyl-5-(trifluoromethyl)furan-2(5H)-ylidene]malonitrile (CAS No. 436097-14-2), and 25 ml of EtOH, and the suspension was stirred for one day by raising the temperature to 55 °C. Purification was then performed by silica gel column chromatography (using hexane, dichloromethane, and MeOH as eluents) to obtain 0.4 g (0.5 mmol) of the compounds represented by formulas 1-5 (yield: 50.8%).

[0460] 1 H NMR (500 MHz, CD2Cl2): δ 0.97 (s, 3H), 1.18 (s, 3H), 1.70 (s, 6H), 2.25 (ABq, 2H), 2.36 (s, 2H), 6.37-6.43 (m, 3H), 6.71 (d, 1H), 7.15 (d, 1H),7.21 (s, 1H), 7.35-7.41 (m, 2H), 7.47 (d, 1H), 7.53-7.61 (m, 6H), 7.85 (d,1H), 7.89-7.98 (m, 2H), 8.11 (d, 1H).

[0461] Synthesis Example 6: Synthesis of compounds represented by chemical formulas 1-6

[0462] [Chemical Formulas 1-6]

[0463]

[0464] Compound 1-6b (yield: 57.7%) was synthesized in the same manner as in step (1) of Synthesis Example 5, except that compound 1-1a of Synthesis Example 1 was used instead of compound 1-2a.

[0465] [Compounds 1-6b]

[0466]

[0467] Compound 1-6c was synthesized using compound 1-6b in the same manner as in step (2) of Synthesis Example 5 (yield: 64.6%).

[0468] [Compounds 1-6c]

[0469]

[0470] Compound 1-6d was synthesized using compound 1-6c in the same manner as in step (3) of Synthesis Example 5 (yield: 39.2%).

[0471] [Compounds 1-6d]

[0472]

[0473] Compounds 1-6d were used in the same manner as in step (4) of Synthesis Example 5 to synthesize compounds represented by chemical formulas 1-6 (yield: 74.2%).

[0474] 1 H NMR (500 MHz, CD2Cl2): δ 0.97 (s, 3H), 1.04 (s, 3H), 1.76 (s, 6H), 2.26 (ABq, 2H), 2.45 (s, 2H), 6.40 (d, 1H), 6.46 (d, 2H), 6.49 (s, 1H), 7.00(s, 2H), 7.36-7.40 (m, 2H), 7.50-7.59 (m, 8H), 7.75 (s, 1H), 7.90 (d, 2H),8.10 (d, 1H), 8.16 (t, 2H).

[0475] Synthesis Example 7: Synthesis of compounds represented by chemical formulas 1-7

[0476] [Chemical Formulas 1-7]

[0477]

[0478] Compounds represented by chemical formulas 1-7 were obtained in the same manner as in Synthetic Example 1, except that: triphenyl(2-selenylmethyl) bromide was used. (CAS No.: 60466-52-6) replaces triphenyl(2-thienylmethyl) bromide in step (1) of Synthetic Example 1. (CAS No.: 23259-98-5).

[0479] Synthesis Example 8: Synthesis of compounds represented by chemical formulas 1-8

[0480] [Chemical Formulas 1-8]

[0481]

[0482] Compounds represented by chemical formulas 1-8 can be obtained in the same manner as in Synthetic Example 1, except that: triphenyl(2-tellurphenylmethyl) bromide is used. Instead of triphenyl(2-thienylmethyl) bromide in step (1) of Synthesis Example 1 (CAS No.: 23259-98-5).

[0483] Synthesis Example 9: Synthesis of compounds represented by chemical formulas 1-9

[0484] [Chemical Formulas 1-9]

[0485]

[0486] Compounds represented by chemical formulas 1-9 can be obtained in the same manner as in Synthesis Example 1, except that compound 1-9a (6-((2-((tert-butyldiphenylsilyl)oxy)ethyl)(ethyl)amino)-3-(dimethylamino)-8,8-dimethyl-8H-indolo[3,2,1-de]acrid-10-carboxaldehyde) is used instead of compound 1-1a in step (1) of Synthesis Example 1.

[0487] [Compounds 1-9a]

[0488]

[0489] Synthesis Example 10: Synthesis of compounds represented by chemical formulas 1-10

[0490] [Chemical Formulas 1-10]

[0491]

[0492] Compounds represented by chemical formulas 1-10 can be obtained in the same manner as in Synthesis Example 1, except that compound 1-10a (3-((2-((tert-butyldiphenylsilyl)oxy)ethyl)(ethyl)amino)-6-(dimethylamino)-8,8-dimethyl-8H-indolo[3,2,1-de]acrid-10-carboxaldehyde) is used instead of compound 1-1a in step (1) of Synthesis Example 1.

[0493] [Compounds 1-10a]

[0494]

[0495] Synthesis Example 11: Synthesis of compounds represented by chemical formulas 1-11

[0496] The compounds represented by chemical formulas 1-11 can be obtained in the same manner as in Synthesis Example 5, except that compound 1-11a (2-(2,5-dimethoxyphenyl)-4,4-dimethyl-4H-thieno[3',2':5,6]pyrido[3,2,1-jk]carbazole) is used instead of compound 1-2a in step (1) of Synthesis Example 5.

[0497] [Chemical Formula 1-11]

[0498]

[0499] [Compounds 1-11a]

[0500]

[0501] Synthesis Example 12: Synthesis of compounds represented by chemical formulas 1-12

[0502] [Chemical Formula 1-12]

[0503]

[0504] Compounds represented by chemical formulas 1-12 can be obtained in the same manner as in Synthetic Example 2, except that: compound 1-12a (4,4,8,8-tetramethyl-4H,8H-selenopheno[3',2':5,6]pyrido[3,2,1-de]acrid-2-carboxaldehyde) is used instead of compound 1-2a in Synthetic Example 2 and triphenyl bromide (thieno[3,2-b]thieno-2-ylmethyl) is used. (CAS No.: 1639046-22-2) replaces triphenyl(2-thienylmethyl)bromide in Synthetic Example 2. (CAS No.: 23259-98-5).

[0505] [Compounds 1-12a]

[0506]

[0507] Synthesis Example 13: Synthesis of compounds represented by chemical formulas 1-13

[0508] [Chemical Formula 1-13]

[0509]

[0510] Compounds represented by chemical formulas 1-13 can be synthesized by the following method. Compound 1-13b is synthesized in the same manner as step (1) of Synthesis Example 1, except that compound 1-13a (4,4,8,8-tetramethyl-4H,8H-thieno[3',2':5,6]pyrido[3,2,1-de]acrid-2-carboxaldehyde) is used instead of compound 1-1a in Synthesis Example 1. Br is introduced into compound 1-13b to obtain compound 1-13c. Compound 1-13d is obtained by reacting compound 1-13c with thieno[3,2-b]thieno-2-boronate pinacol ester (CAS No.: 1004784-50-2). Compound 1-13e is obtained from compound 1-13d in the same manner as step (2) of Synthesis Example 1. The compound represented by chemical formula 1-13 was obtained by the same method as step (3) of synthesis example 1, except that compound 1-13e was used instead of compound 1-1c.

[0511] [Compounds 1-13a] [Compounds 1-13b]

[0512]

[0513] [Compounds 1-13c] [Compounds 1-13d]

[0514]

[0515] [Compounds 1-13e]

[0516]

[0517] Synthesis Example 14: Synthesis of compounds represented by chemical formulas 1-14

[0518] [Chemical Formula 1-14]

[0519]

[0520] Compounds represented by chemical formulas 1-14 can be synthesized by the following method. Compound 1-14b is synthesized in the same manner as step (1) of Synthesis Example 1, except that: compound 1-13a (4,4,8,8-tetramethyl-4H,8H-thieno[3',2':5,6]pyrido[3,2,1-de]acrid-2-carboxaldehyde) is used instead of compound 1-1a in Synthesis Example 1 and triphenyl bromide (thieno[3,2-b]thieno-2-ylmethyl) is used. (CAS No.: 1639046-22-2) replaces triphenyl(2-thienylmethyl)bromide in Synthetic Example 1. (CAS No.: 23259-98-5). Br was introduced into compound 1-14b to obtain compound 1-14c. Compound 1-14d was obtained by Suzuki coupling reaction of compound 1-14c and thiophene-2-boronate pinacol ester (CAS No.: 193978-23-3). Compound 1-14e was obtained from compound 1-14d by the same method as step (2) of Synthetic Example 1 (Vilsmeier-Haack reaction). Compounds represented by chemical formula 1-14 can be obtained by the same method as step (3) of Synthetic Example 1, except that compound 1-14e is used instead of compound 1-1c.

[0521] [Compounds 1-14b] [Compounds 1-14c]

[0522]

[0523] [Compounds 1-14d] [Compounds 1-14e]

[0524]

[0525] Synthesis Example 15: Synthesis of compounds represented by chemical formulas 1-15

[0526] [Chemical Formula 1-15]

[0527]

[0528] Compounds represented by chemical formulas 1-15 can be synthesized by the following method. Compound 1-13b is synthesized in the same manner as step (1) of Synthesis Example 1, except that: compound 1-13a (4,4,8,8-tetramethyl-4H,8H-thieno[3',2':5,6]pyrido[3,2,1-de]acrid-2-carboxaldehyde) is used instead of compound 1-1a in Synthesis Example 1. Br is introduced into compound 1-13b to obtain compound 1-13c. Compound 1-13d is obtained by Suzuki coupling reaction of compound 1-13c and thieno[3,2-b]thieno-2-boronate (CAS No.: 1004784-50-2). Compound 1-15f is obtained by Suzuki coupling reaction of compound 1-15e and thieno-2-boronate (CAS No.: 193978-23-3). Compound 1-15g was obtained from compound 1-15f by the same method as step (2) of Synthesis Example 1 (Vilsmeier-Haack reaction). The compound represented by chemical formula 1-15 can be obtained by the same method as step (3) of Synthesis Example 1, except that compound 1-15g is used instead of compound 1-1c.

[0529] [Compounds 1-15e] [Compounds 1-15f]

[0530]

[0531] [Compound 1-15g]

[0532]

[0533] Synthesis Example 16: Synthesis of compounds represented by chemical formulas 1-16

[0534] [Chemical Formula 1-16]

[0535]

[0536] Compounds represented by chemical formulas 1-16 can be synthesized by the following method. Compound 1-16b is synthesized by the same method as step (1) of Synthesis Example 1, except that: compound 1-13a (4,4,8,8-tetramethyl-4H,8H-thieno[3',2':5,6]pyrido[3,2,1-de]acrid-2-carboxaldehyde) is used instead of compound 1-1a in Synthesis Example 1, and compound 1-16a (4-((bromotriphenyl-15-n-phosphino)methyl)-2-(2-ethylhexyl)isoindoline-1,3-dione) is used instead of triphenyl(2-thienomethyl)bromodide in Synthesis Example 1. (CAS No.: 23259-98-5). Compound 1-16c was obtained from compound 1-16b by the same method as step (2) of Synthetic Example 1 (Vilsmeier-Haack reaction). Compounds represented by chemical formula 1-16 can be obtained by the same method as step (3) of Synthetic Example 1, except that compound 1-16c is used instead of compound 1-1c.

[0537] [Compounds 1-16a] [Compounds 1-16b]

[0538]

[0539] [Compound 1-16c]

[0540]

[0541] Synthesis Example 17: Synthesis of compounds represented by chemical formulas 1-17

[0542] [Chemical Formula 1-17]

[0543]

[0544] The compounds represented by chemical formulas 1-17 can be synthesized by the following method. Compound 1-17b is synthesized in the same manner as step (1) of Synthesis Example 1, except that: compound 1-13a (4,4,8,8-tetramethyl-4H,8H-thieno[3',2':5,6]pyrido[3,2,1-de]acrid-2-carboxaldehyde) is used instead of compound 1-1a in Synthesis Example 1, and compound 1-17a (bromo((5-(2-(2-ethylhexyl)-1,3-dioxo-7-(thieno-2-yl)isoindoline-4-yl)thieno-2-yl)methyl)triphenyl) (This is used to replace triphenyl(2-thienylmethyl)bromide in Synthetic Example 1) (CAS No.: 23259-98-5). Compound 1-17c was obtained from compound 1-17b by the same method as step (2) of Synthetic Example 1 (Vilsmeier-Haack reaction). The compound represented by chemical formula 1-17 can be obtained by the same method as step (3) of Synthetic Example 1, except that compound 1-17c is used instead of compound 1-1c.

[0545] [Compounds 1-17a] [Compounds 1-17b]

[0546]

[0547] [Compounds 1-17c]

[0548]

[0549] In comparative examples 1 to 6, compounds represented by chemical formulas 1-1C to 1-6C were synthesized according to conventional methods in the art.

[0550] [Chemical Formula 1-1C] [Chemical Formula 1-2C] [Chemical Formula 1-3C]

[0551]

[0552] [Chemical Formula 1-4C] [Chemical Formula 1-5C] [Chemical Formula 1-6C]

[0553]

[0554] Examples 1A to 17A and Comparative Examples 1A to 6A: Evaluation of Device Fabrication

[0555] The coating compositions were prepared by mixing the compounds of Synthetic Examples 1 to 17 and Comparative Examples 1 to 6 with a polymethyl methacrylate (PMMA) matrix polymer in a cyclohexanone solvent. The amounts of the compounds used in the coating compositions are listed in Table 3. After forming a first electrode (ITO, 100 nm) and an Al2O3 charge-blocking layer (40 nm) on a glass substrate using vacuum evaporation, the compositions were spin-coated onto the Al2O3 charge-blocking layer to form an active layer 200 nm thick. Then, silver was deposited thereon to form a second electrode 100 nm thick, thereby manufacturing the evaluation devices (optical modulators for evaluation) according to Examples 1A to 17A and Comparative Examples 1A to 6A.

[0556] Examples 1B to 17B and Comparative Examples 1B to 6B:

[0557] Each evaluation device was manufactured in the same manner as in Examples 1A to 17A and Comparative Examples 1A to 6A, except that PC (polycarbonate) was used instead of polymethyl methacrylate (PMMA) as the matrix polymer.

[0558] Evaluation 1: Measurement of dipole moment, hyperpolarizability, and glass transition temperature

[0559] The dipole moments of the compounds represented by chemical formulas 1-1 to 1-17 according to synthesis examples 1 to 17 and the compounds represented by chemical formulas 1-1C to 1-6C according to synthesis comparative examples 1 to 6 were calculated using DFT (B3LYP, M062X), and the results are shown in Table 1.

[0560] In addition, the hyperpolarizability of the compounds represented by chemical formulas 1-1 to 1-17 according to synthesis examples 1 to 17 and the compounds represented by chemical formulas 1-1C to 1-6C according to synthesis comparative examples 1 to 6 were calculated by using DFT (B3LYP, M062X), and the results are shown in Table 1.

[0561] (Table 1)

[0562]

[0563] Referring to Table 1, it is confirmed that the compounds according to Synthetic Examples 1 to 17 exhibit larger or comparable dipole moments and higher absolute values ​​of hyperpolarizability than those of Synthetic Comparative Examples 1 to 6. Therefore, the compounds according to Synthetic Examples 1 to 17 are expected to provide high or improved electro-optic coefficients, thereby enabling improved performance of optical modulators (e.g., in active layers, nonlinear optically active organic materials, or any combination thereof) that include such compounds, thus enabling improved performance of optical transmission-based communications using such optical modulators and / or devices including them.

[0564] The glass transition temperatures of the compounds synthesized according to Examples 1 to 17 and Comparative Examples 1 to 6 were measured by DTA (differential thermal analysis), and their decomposition temperatures were measured by TGA (thermogravimetric analysis). The results for the compounds synthesized in Examples 1, 2, 3, 5 and 6 and Comparative Example 2 are shown in Table 2.

[0565] (Table 2)

[0566]

[0567] Referring to Table 2, the compounds of synthetic Examples 1, 2, 3, 5 and 6 exhibit higher glass transition temperatures and higher decomposition temperatures than the compound of Synthetic Comparative Example 2, which confirms excellent or improved thermal stability.

[0568] Evaluation 2: Measurement of Electro-optic Coefficient

[0569] After applying a voltage to the evaluation devices according to Examples 1A to 17A and Comparative Examples 1A to 6A, as well as Examples 1B to 17B and Comparative Examples 1B to 6B, they were subjected to polarization at 85°C to 150°C for 40 minutes and rapidly cooled to 25°C, and then the applied voltage was reduced to 0 V.

[0570] The electro-optic coefficients (r) of the evaluation devices according to Examples 1A to 17A and Comparative Examples 1A to 6A, as well as Examples 1B to 17B and Comparative Examples 1B to 6B, were measured and calculated at 20 Vpp (voltage peak-to-peak) based on Equation 1. 33 The results of the evaluation devices based on Examples 1A and 1B, Example 2B, Example 3B, Example 5A and 6B, and Comparative Examples 1A and 2A are shown in Table 3.

[0571] (Table 3)

[0572]

[0573] In Table 3, “Concentration 1” refers to the concentration (by weight %) of each compound relative to the matrix polymer and the total amount of each compound, and “Concentration 2” refers to the concentration (by weight %) of the matrix polymer and compounds relative to the total amount of the coating composition.

[0574] Referring to Table 3, compared with those of Comparative Examples 1A and 2A, the evaluation devices according to Examples 1A, 1B, 2B, 3B, 5A, and 6B exhibit superior or significantly improved electro-optic coefficients (r). 33 This demonstrates that the evaluation devices according to embodiments 1A, 1B, 2B, 3B, 5A, and 6B enable improved performance in optical transmission-based communications.

[0575] While the inventive concept has been described in conjunction with exemplary embodiments now considered practical, it will be understood that the inventive concept is not limited to such exemplary embodiments. Rather, the scope of the inventive concept is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

[0576] <Explanation of Symbols>

[0577] 100: Optical modulator; 2: Mach-Zehnder interferometer

[0578] 3: Input section 4: Branch section

[0579] 5: First branch waveguide; 6: Second branch waveguide

[0580] 7: Combination section 8: Output section

[0581] 14: First electrode; 30: Second electrode

[0582] 20: Active layer

Claims

1. A compound, represented by chemical formula 1: [Chemical Formula 1] in, In chemical formula 1, Ar 1 Ar 2 And Ar 3 Each of these groups is independently a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, or any combination thereof. X 1 For single bonds, -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-(CR f R g ) n1 -、-CR ff R gg -、-C(R m )=C(R n - or -C(R) p ) = N-, where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each of these elements is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy. R bb R cc R dd R ee R ff and R gg Each is independently (CH2) x Alternatively, heteroatoms such as O, N, S, Se, or Te may be present, where (CH2) x x is a positive integer, and R is a positive integer. bb and R cc The pair, R dd and R ee The pair, or R ff and R gg The pairs connect to each other to form the first ring structure, and In -(CR f R g ) n1 In this context, n1 is either 1 or 2. L represents a single bond, -O-, -S-, -Se-, -Te-, or -NR. a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-(CR f R g ) n1 -、-CR ff R gg -、-C(R m )=C(R n )-、-C(R mm )=C(R nn - or -C(R) p ) = N-, where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each of these elements is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy. R bb R cc R dd R ee R ff R gg R mm and R nn Each is independently (CH2) y Alternatively, heteroatoms such as O, N, S, Se, or Te may be present, where (CH2) y In this context, y is a positive integer, and R is a positive integer. bb and R cc The pair, R dd and R ee The pair, R ff and R gg The pair, or R mm and R nn The pairs connect to each other to form a second ring structure, and In -(CR f R g ) n1 In this context, n1 is either 1 or 2. Where L is -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1 -、-C(R m )=C(R n - or -C(R) p When )=N-, L is optionally connected to Ar. 1 Or Ar 2 To form a third ring structure, Cy can be, independently, a substituted or unsubstituted C6- to C10 arylene, a substituted or unsubstituted C3- to C10 heteroarylene, a substituted or unsubstituted C3- to C10 cycloalkyl, a substituted or unsubstituted C3- to C10 cycloalkenyl, a substituted or unsubstituted C3- to C10 heterocyclic alkyl, a substituted or unsubstituted C3- to C10 heterocyclic alkenyl, or any combination thereof. EWG is: CR a R b , where R a and R b Each group is independently a cyano or cyano-containing group; substituted or unsubstituted groups having a group selected from C=O, C=S, C=Se, C=Te, and CR. a R b At least one functional group of a C6 to C30 hydrocarbon ring group, wherein R a and R b Each group is independently a cyano or cyano-containing group; substituted or unsubstituted groups having a group selected from C=O, C=S, C=Se, C=Te, and CR. a R b At least one functional group of a C2 to C30 heterocyclic group, wherein R a and R b Each group is independently a cyano group or a cyano-containing group; or any combination thereof. R 1 To R 4 Each of the following is independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, substituted or unsubstituted C2 to C30 acyl, halogen, cyano (-CN), cyano-containing group, nitro, pentafluorosulfuryl (-SF5), hydroxyl, amino, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphate or its salt, -SiR a R b R c , or any combination thereof, where R a R b and R c Each is independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group. x is an integer from 0 to 5. y is an integer from 1 to 5. z is an integer from 0 to 5, and n is an integer from 1 to 5.

2. The compound according to claim 1, wherein... Compounds represented by chemical formula 1 are represented by chemical formula 2: [Chemical Formula 2] in, In chemical formula 2, EDG represents the electron donor portion, as indicated by chemical formula 2A: [Chemical Formula 2A] Among them, in chemical formula 2 and chemical formula 2A, X 1 L, Cy, Ar 3 R 1 To R 4 EWG, x, y, z, and n are the same as in chemical formula 1. Y 1 To Y 7 Each is independently N or CR k , where R k It is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C1 to C10 alkoxy, or adjacent R k They are connected to each other to form substituted or unsubstituted C6 to C30 aromatic groups, substituted or unsubstituted C3 to C30 heteroaromatic groups, or fused rings thereof, and * indicates the connection point with chemical formula 2.

3. The compound according to claim 2, wherein, In chemical formula 2, Y 4 For N or CR k , where R k It is a halogen, cyano, C1 to C10 haloalkyl, C1 to C10 cyanoalkyl, or amino group, or Y 7 For N or CR k , where R k It is a halogen, cyano, C1 to C10 haloalkyl, C1 to C10 cyanoalkyl, or amino group, and X 1 is -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1 -、-C(R m )=C(R n - or -C(R) p )=N-, where R a1 R a2 R b R c R d R e R f R g R m R n and R p Each is independently a halogen, a C1 to C20 haloalkyl, or a C1 to C20 cyanoalkyl, and wherein -(CR f R g ) n1 In the -, n1 is either 1 or 2.

4. The compound according to claim 2, wherein... In chemical formula 2, EDG is represented by any one of the multiple parts represented by chemical formula 2AA: [Chemical formula 2AA] in, In the chemical formula 2AA, X 1 L, Y 1 To Y 7 And Ar 3 Same as in chemical formula 2A, X 11 With X in chemical formula 1 1 Same, and * indicates the adjacent (C(R)) of chemical formula 2. 1 )=C(R 2 ))x or (Cy) y Connection points of functional groups.

5. The compound according to claim 1, wherein... In chemical formula 1, the first ring structure and the second ring structure are each independently a spirocyclic structure or a fused ring structure.

6. The compound according to claim 5, wherein the spirocyclic structure is one of the plurality of parts represented by group 1: [Group 1] in, In group 1, X a and X b Each of the following can be independently represented as -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, -NR a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、or-GeR dd R ee -, where R a1 R a2 R b R c R d and R e Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy, and R bb R cc R dd and R ee Each is independently (CH2) z Alternatively, heteroatoms such as O, N, S, Se, or Te may be present, where (CH2) z In this context, z is a positive integer, and R is a positive integer. bb and R cc The pair or R dd and R ee They connect to each other to form a fourth ring structure. L a -O-, -S-, -Se-, -Te-, -NR a1 -、-BR a2 -、-SiR b R c -、-GeR d R e -、-(CR f R g ) n1 -、-C(R p ) = N- or single bond, where R a1 R a2 R b R c R d R e R f R g and R p Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy, and wherein -(CR f R g ) n1 In the -, n1 is either 1 or 2. One or more hydrogen atoms in each ring are optionally replaced by at least one substituent selected from: deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, and substituted or unsubstituted C6 to C20 aryloxy. CH in the aromatic rings present in parts (3), (4), (5), (6) and (7) are optionally replaced by N.

7. The compound according to claim 1, wherein... In chemical formula 1, Ar 3 For any one of the multiple parts represented by group 2: [Group 2] in, In group 2, X 21 and X 23 Each of these can be independently represented as a single bond, -O-, -S-, -Se-, -Te-, -S(=O)-, -S(=O)2-, or -NR. a1 -、-BR a2 -、-SiR b R c -、-SiR bb R cc -、-GeR d R e -、-GeR dd R ee -、-CR f R g - or -CR ff R gg -, where R a1 R a2 R b R c R d R e R f and R g Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C6 to C20 aryloxy, and R bb R cc R dd R ee R ff and R gg Each is independently (CH2) w Alternatively, heteroatoms such as O, N, S, Se, or Te may be present, where (CH2) w In this context, w is a positive integer, and R is a positive integer. bb and R cc The pair, R dd and R ee The pair, or R ff and R gg They connect to each other to form a fifth ring structure. R 21 The following are groups: hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, substituted or unsubstituted C2 to C30 acyl, halogen, cyano (-CN), cyano-containing groups, nitro, pentafluorosulfuryl (-SF5), hydroxyl, amino, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphate or its salt, -SiR. a R b R c , or any combination thereof, where R a R b and R c Each is independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group. Y 21 To Y 28 Each is independently N or CR k , where R k It is hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C1 to C10 alkoxy, or adjacent R k Optionally linked together to form substituted or unsubstituted C6 to C30 aromatic groups, substituted or unsubstituted C3 to C30 heteroaromatic groups, or fused rings thereof, provided that, in group 2, the Y in part (4) 21 To Y 24 Y in any one of the parts (5) 25 To Y 28 Y in any one of the parts (6) 25 To Y 28 Y in any one or part of (7) 25 To Y 28 Any one of them is adjacent to chemical formula 1 (C(R) 1 )=C(R 2 )) x Or (Cy) y Groups linked by groups, *=* represents the presence of X in chemical formula 1. 1 The ring-fused portion, and -* indicates the (C(R) adjacent to chemical formula 1. 1 )=C(R 2 )) x Or (Cy) y Connection points of functional groups.

8. The compound according to claim 1, wherein... In chemical formula 1, Cy is each independently any one of the multiple parts represented by group 3: [Group 3] in, In group 3, Z 11 Z 12 and Z 13 Each of these can be independently represented as O, S, Se, Te, S(=O), S(=O)2, NR a or SiR b R c , where R a R b and R c Each of these elements is independently hydrogen, C1 to C10 alkyl, C1 to C10 haloalkyl, -SiH3, C1 to C10 alkylsilyl, -NH2, C1 to C10 alkylamino, C6 to C12 aryl, C3 to C12 heteroaryl, halogen, cyano, or any combination thereof. Z 20 and Z 21 Each can be independently represented as O, S, Se, or Te. R b and R c Each exists independently or connects to form a sixth ring structure, and * indicates the connection point with chemical formula 1.

9. The compound according to claim 1, wherein... In chemical formula 1, EWG is a cyclic group represented by chemical formula 3: [Chemical Formula 3] in, In chemical formula 3, EWG' is a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C3 to C30 heteroaryl, or a substituted or unsubstituted C3 to C30 heterocyclic alkenyl. Z is O, S, Se, Te, or CR a R b , where R a and R b Each is independently a cyano group or a cyano-containing group, and * indicates the connection point with chemical formula 1.

10. The compound according to claim 1, wherein... In Formula 1, EWG represents any of the cyclic groups from Formula 3A to Formula 3G: [Chemical Formula 3A] in, In chemical formula 3A, Z 1 For O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group. Z 2 For O, S, Se, Te, or CR a R b , where R a and R b Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group. Z 3 For N or CR c , where R c It is hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group. R 11 R 12 R 13 R 14 and R 15 The same or different and independently comprising hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), cyano-containing groups, or any combination thereof, wherein R 12 and R 13 and R 14 and R 15 They exist independently or are connected to each other to form dense aromatic rings. n is 0 or 1, and * indicates the connection point with chemical formula 1. [Chemical Formula 3B] In the chemical formula 3B, Z 1 For O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group. Z 2 For O, S, Se, Te, or CR a R b , where R a and R b Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group. Z 3 For O, S, Se, Te, or C(R) a (CN), where R a It is hydrogen, cyano (-CN), or C1 to C10 alkyl. R 11 and R 12 Each of the following is independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), or any combination thereof, and * indicates the connection point with chemical formula 1. [Chemical formula 3C] In the chemical formula 3C, Z 1 For O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group. Z 2 For O, S, Se, Te, or CR a R b , where R a and R b Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group. R 11 R 12 and R 13 The same or different and each independently being hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), or any combination thereof, and * indicates the connection point with chemical formula 1. [Chemical Formula 3D] In chemical formula 3D, Z 1 For O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group. Z 2 For O, S, Se, Te, or CR a R b , where R a and R b Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group. Z 3 For N or CR c , where R c It is hydrogen or a substituted or unsubstituted C1 to C10 alkyl group. G 1 For O, S, Se, Te, SiR x R y , or GeR z R w , where R x R y R z and R w They may be the same or different and are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, or substituted or unsubstituted C6 to C20 aryl. R 11 R 12 and R 13 The same or different and each independently being hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano, cyano-containing group, or any combination thereof, wherein R 12 and R 13 They exist independently or are connected to each other to form dense aromatic rings. n is 0 or 1, and * indicates the connection point with chemical formula 1. [Chemical formula 3E] In the chemical formula 3E, Z 1 For O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group. Z 2 For O, S, Se, Te, or CR a R b , where R a and R b Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group. Z 3 For N or CR c , where R c It is hydrogen or a substituted or unsubstituted C1 to C10 alkyl group. G 2 For O, S, Se, Te, SiR x R y , or GeR z R w , where R x R y R z and R w They may be the same or different and are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, or substituted or unsubstituted C6 to C20 aryl. R 11 R 12 and R 13 The same or different and each independently being hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano, cyano-containing groups, or any combination thereof. n is 0 or 1, and * indicates the connection point with chemical formula 1. [Chemical formula 3F] In the chemical formula 3F, Z 1 For O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group. Z 2 For O, S, Se, Te, or CR a R b , where R a and R b Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group. R 11 It can be hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), cyano-containing groups, or any combination thereof. G 3 For O, S, Se, Te, SiR x R y , or GeR z R w , where R x R y R z and R w They are the same or different and are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, or substituted or unsubstituted C6 to C20 aryl, and * indicates the connection point with chemical formula 1. [Chemical formula 3G] In the chemical formula 3G, Z 1 For O, S, Se, Te, or CR a R b , where R a and R b Each group is independently a cyano group or a cyano-containing group. R 11 To R 13 It can be hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C4 to C30 heteroaryl, halogen, cyano (-CN), cyano-containing groups, or any combination thereof. G 3 For O, S, Se, Te, SiR x R y , or GeR z R w , where R x R y R z and R w They are the same or different and are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, or substituted or unsubstituted C6 to C20 aryl, and * indicates the connection point with chemical formula 1.

11. The compound according to claim 1, wherein... The compound has a hyperpolarizability of less than or equal to -170.

12. The compound according to claim 1, wherein... The compound has a dipole moment greater than or equal to 15 Debye.

13. The compound according to claim 1, wherein... The compound has a glass transition temperature of less than or equal to 150°C.

14. Nonlinear optically active organic materials, including compounds according to any one of claims 1 to 13.

15. An optical modulator comprising the compound according to any one of claims 1 to 13.

16. The optical modulator of claim 15, comprising: The first and second electrodes facing each other; as well as The active layer between the first electrode and the second electrode The active layer comprises a compound according to any one of claims 1 to 13.

17. The optical modulator of claim 16, wherein... The optical modulator further includes a charge blocking layer between the first electrode and the active layer.

18. The optical modulator according to claim 16, wherein The active layer further comprises a matrix polymer, a photoconductive polymer, a photosensitizer, or any combination thereof.

19. Optical equipment, including: Input section; Branch section; waveguide; Combined parts; and Output section, The waveguide includes an optical modulator according to any one of claims 15 to 18.

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