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KR-20260062450-A - Compound for organic photovoltaic device and photovoltaic device, image sensor and electronic device including it

KR20260062450AKR 20260062450 AKR20260062450 AKR 20260062450AKR-20260062450-A

Abstract

The present invention discloses a compound for organic photovoltaic devices according to Formula 1, and an organic photovoltaic device, image sensor, and electronic device comprising the same. The compound represented by Formula 1 is a material with high sensitivity and high heat resistance, and when applied to an organic photovoltaic device, it can significantly improve the efficiency and stability of the device.

Inventors

  • 한승훈
  • 이송민
  • 최창은
  • 이형동
  • 윤기환

Assignees

  • 덕산네오룩스 주식회사

Dates

Publication Date
20260507
Application Date
20241029

Claims (8)

  1. Compounds represented by Chemical Formula 1: <Chemical Formula 1> <Chemical Formula A-1><Chemical Formula A-2> In the above chemical formula 1, A is the chemical formula A-1, and X and Y are independently O, S, Se, or Te, and Ar is selected from the group consisting of a C6 – C60 aryl group; a fluorenyl group; a C2 – C60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, Se, and Te; and N(R a )(R b ). L1 and L2 are independently selected from the group consisting of single bonds; C6 – C60 arylene groups; fluorenylene groups; C2 – C60 heterocyclic groups comprising at least one heteroatom among O, N, S, Si, Se, and Te; C3 – C60 aliphatic groups; and fused groups of C3 – C60 aliphatic groups and C6 – C60 aromatic groups, and The B ring has the chemical formula A-2, where x is an integer from 0 to 3, and V 1 and V 2 are independently O, S, Se, Te, N(R') or C(R')(R"), and when x is 2 or 3, multiple V 2 are the same or different from each other, and W 1 is CR' or N, provided that when x is 0, W 1 is N, and R1 , R', and R" are independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; C6 – C60 aryl group; fluorenyl group; C2 – C60 heterocyclic group containing at least one heteroatom among O, N, S, Si, and Se; C3 – C60 aliphatic group; fused group of a C3 – C60 aliphatic ring and a C6 – C60 aromatic ring; C1 – C30 alkyl group; C2 – C30 alkenyl group; C2 – C30 alkynyl group; C1 – C30 alkoxy group; C6 – C30 aryloxy group; and L'-N( Ra )( Rb ), and adjacent R1s can bond to each other to form a ring, and R' and R" can combine with each other to form a ring, a is an integer from 0 to 4, and The above R a and R b are independently selected from the group consisting of a C 6 -C 30 aryl group; a fluorenyl group; a C 2 -C 30 heterocyclic group comprising at least one heteroatom among O, N, S, Si, Se, and Te; and a C 3 -C 30 aliphatic group, and The above L' is selected from the group consisting of a single bond; a C6 – C60 arylene group; a fluorenylene group; a C2 – C60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, Se, and Te; a C3 – C60 aliphatic group; and a fused group of a C3 – C60 aliphatic ring and a C6 – C60 aromatic ring, and The above aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic cyclic group, fused cyclic group, alkyl group, alkenyl group, alkyneyl group, alkoxy group, aryloxy group, a ring formed by the bonding of adjacent R1s together, and a ring formed by the bonding of R' and R" together are each deuterium; halogen; cyano group; silane group substituted or unsubstituted with a C1 - C20 alkyl group or a C6 - C20 aryl group; phosphine oxide substituted or unsubstituted with a C1 - C20 alkyl group or a C6 - C20 aryl group; C1 - C20 alkoxy group; C6 -C30 aryloxy group; C1 - C20 alkyl group; C2 - C20 alkenyl group; C2 - C20 of It can be substituted with one or more substituents selected from the group consisting of an alkyne group; a C6-C30 aryl group; a fluorene group; a C2-C60 heterocyclic group containing at least one heteroatom among O, N , S, Si, Se and Te; a C3 - C30 aliphatic group; a fused group of a C3-C30 aliphatic ring and a C6 - C30 aromatic ring; and combinations thereof, and adjacent substituents can bond to each other to form a ring, and the hydrogen of the substituents can be replaced with deuterium.
  2. In Article 1, The above chemical formula A-1 is a compound represented by one of the following chemical formulas A-1-1 to A-1-4: <Chemical Formula A-1-1><Chemical Formula A-1-2> <Chemical Formula A-1-3><Chemical Formula A-1-4> In the above formulas A-1-1 to A-1-4, V1 , V2 , W1 , R1 , and a are as defined in claim 1, and V3 and V4 are as defined in V2 .
  3. In Article 1, The compound represented by the above chemical formula 1 is one of the following compounds: .
  4. In Article 1, The above compound is a compound having a maximum absorption wavelength of 650 nm or more and 1300 nm or less in the thin film state.
  5. An organic photovoltaic device comprising a first electrode, a second electrode, and an active layer between the first electrode and the second electrode, wherein An organic photovoltaic device characterized in that the active layer comprises the compound of claim 1.
  6. In Paragraph 5, An organic photovoltaic device characterized in that the active layer comprises a p-type semiconductor compound and an n-type semiconductor compound, and the p-type semiconductor compound is the compound of claim 1.
  7. An image sensor comprising the organic photovoltaic element of claim 5.
  8. An electronic device comprising the image sensor of claim 7.

Description

Compound for organic photovoltaic device and photovoltaic device, image sensor and electronic device including it The present invention relates to a compound for an organic photovoltaic device and an organic photovoltaic device, image sensor, and electronic device comprising the same. Photovoltaic devices are components capable of converting light into electrical signals using the photoelectric effect, and they can be applied to image sensors. Therefore, the development of photovoltaic devices has been continuously ongoing to develop image sensors. As technology development progresses, the resolution of image sensors increases, and consequently, the size of pixels is also becoming smaller. However, as the pixel size decreases, the absorption area shrinks, which can lead to a decrease in sensitivity, and research on optoelectronic devices is actively underway to overcome this. Recently, there has been a shift from silicon materials or polymer materials produced using inkjet technology, which are primarily used as optoelectronic devices, to organic materials produced using vacuum deposition. Organic materials possess high absorption coefficients and can be designed to selectively absorb light in specific wavelength ranges depending on their molecular structure. In other words, since organic materials can selectively detect light in desired color ranges by absorbing it, they can simultaneously replace existing optoelectronic devices and color filters. Therefore, organic materials must be capable of providing high sensitivity. Furthermore, there is a need for organic optoelectronic devices that exhibit high efficiency even in high-temperature processes such as vacuum deposition. To address this, it is necessary to develop organic materials with excellent heat resistance. Therefore, research is currently needed to develop high-sensitivity and high-heat-resistant materials to realize superior organic optoelectronic devices. FIGS. 1 and FIGS. 2 are drawings showing a stacked structure of an organic photovoltaic device according to an embodiment of the present invention. Figure 3 shows the IR spectrum of comparative compound A. Figure 4 shows the IR spectrum of compound P52 of the present invention. As used in this specification, the terms "aryl group," "arylene group," and "aromatic ring" refer to hydrocarbon aromatic rings, each having 6 to 60 carbon atoms unless otherwise noted, but are not limited thereto. In the present invention, an aryl group or an arylene group includes a single ring, a polycyclic ring, and a condensed ring, etc. As used in this specification, the term "fluorenyl group" refers to a substituted or unsubstituted fluorenyl group, and the term "fluorenylene group" refers to a substituted or unsubstituted fluorenylene group. The fluorenyl group or fluorenylene group used in the present invention includes a spiro compound formed by R and R' being bonded to each other in the following structure, and also includes a compound in which adjacent R" are bonded to each other to form a ring. "Substituted fluorenyl group" and "substituted fluorenylene group" mean that at least one of R, R', and R" in the following structure is a substituent other than hydrogen, and in the chemical formula below, R" may be 1 to 8. In this specification, regardless of the valence, the fluorenyl group, fluorenylene group, etc. may be described as a fluoren group or fluoren. The term "spyro compound" as used in this specification refers to a compound having a "spyro linkage," where a spyro linkage is a connection formed by two rings sharing only one atom. In this case, the atom shared between the two rings is called a "spyro atom," and depending on the number of spyro atoms contained in a compound, they are respectively called "monospyro-," "diespyro-," and "trispyro-" compounds. The term “heterocyclic group” as used in this specification includes not only aromatic heterocyclic groups such as “heteroaryl groups” or “heteroarylene groups” but also non-aromatic heterocyclic groups, and unless otherwise noted, means a ring having 2 to 60 carbon atoms containing one or more heteroatoms, but is not limited thereto. Unless otherwise noted, the term “heteroatom” as used in this specification refers to an element other than carbon, such as N, O, S, P, Si, Se, Te, etc., and may include a heterocyclic group such as SO₂ , P=O, etc., as in the following compounds, instead of carbon forming the ring. In addition, heterocyclic rings include monocyclic, polycyclic, or condensed rings containing heteroatoms, and in the case of condensed rings, if at least one of the condensed rings is a ring containing a heteroatom, it is defined as a heterocyclic ring. For example, heterocyclic rings such as furan, dihydrofuran, thiophene, pyrrole, pyridine, etc., and aromatic rings such as benzene, naphthalene, phenanthrene, etc., or aliphatic rings such as cyclopentane, cyclohexane, etc., are condensed to form a condensed ring, and in the case of a spiro