US 11,081,651 B2Granted

Organic semiconductor element, organic semiconductor composition, method of manufacturing organic semiconductor film, organic semiconductor film, and compound and polymer using the same

AssigneesFUJIFILM Corporation, The University of Tokyo

InventorsKenji Shirokane, Eiji Fukuzaki, Yukio Tani, Fumiko Tamakuni, Yoshihisa Usami, Tetsuya Watanabe, Toshihiro Okamoto, Junichi Takeya

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Abstract

An organic semiconductor element in which an organic semiconductor layer contains a compound of Formula (1), a compound of Formula (2), and/or a compound of Formula (3) or contains a polymer having a structure of any one of formed by Formulae (8) to (10): in which X1 represents a nitrogen atom or CRa, and rings A to B each represent a specific nitrogen-containing ring; Y1 represents an oxygen atom, a sulfur atom, CRb2, or NRc; V1 represents NRd, an oxygen atom, a sulfur atom, or a selenium atom; Ra to Rd each represent a hydrogen atom or a substituent; R1 represents a specific substituent, and p is an integer of 0 to 2; n represents 1 or 2; and * represents a bonding site.

Claims18

Dependent claims

An organic semiconductor element, comprising:

an organic semiconductor layer containing a compound represented by Formula (1), a compound represented by Formula (2), and/or a compound represented by Formula (3), or containing a polymer having at least one structural unit represented by any one of Formulae (8) to (10),
in each formula, X1 represents a nitrogen atom or CRa, rings A and B each are a 5-membered or 6-membered aromatic heterocyclic ring having a nitrogen atom as a ring-constituting atom or a fused ring including a 5-membered or 6-membered aromatic heterocyclic ring having a nitrogen atom as a ring-constituting atom,
Y1 represents an oxygen atom, a sulfur atom, CRb2, or NRc,
V1 represents NRd, an oxygen atom, a sulfur atom, or a selenium atom,
Ra, Rb, Rc, and Rd each represent a hydrogen atom or a substituent,
R1 represents a halogen atom or a group represented by Formula (W), and p is an integer of 0 to 2,
n represents 1 or 2,
* represents a bonding site,
*-L-T Formula (W)
in Formula (W), L is a single bond, or a divalent group represented by any one of Formulae (L-1) to (L-25), or a divalent group formed by bonding two or more divalent groups represented by any of (L-1) to (L-25),
T represents a hydrogen atom, a halogen atom, or a cyano group,
* represents a bonding site,
in Formulae (L-1) to (L-25), the wavy line portion represents a bonding site to a ring structure represented by Formula (1) to (3), and (8) to (10), or a bonding site to * of a divalent group represented by any one of Formulae (L-1) to (L-25),
* represents a bonding site to T, or a bonding site to a wavy line portion of a divalent group represented by any one of Formulae (L-1) to (L-25),
in Formulae (L-1), (L-2), (L-6), and (L-13) to (L-24), RA represents a hydrogen atom or a substituent,
in Formula (L-13), m is an integer of 1 to 4, m in Formulae (L-14) and (L-15) is an integer of 1 to 3, and m in Formulae (L-16) to (L-20) is 1 or 2, and m in Formula (L-22) is an integer of 1 to 6,
in Formulae (L-20) and (L-24), RN represents a hydrogen atom or a substituent, and
in Formula (L-25), Rsi represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group.

15 more elements

An organic semiconductor composition comprising:

a compound represented by Formula (1), a compound represented by Formula (2), and/or a compound represented by Formula (3), or a polymer having at least one structural unit represented by any one of Formulae (8) to (10);
and
a solvent,
in each formula, X1 represents a nitrogen atom or CRa, rings A and B each are a 5-membered or 6-membered aromatic heterocyclic ring having a nitrogen atom as a ring-constituting atom or a fused ring including a 5-membered or 6-membered aromatic heterocyclic ring having a nitrogen atom as a ring-constituting atom,
Y1 represents an oxygen atom, a sulfur atom, CRb2, or NRc,
V1 represents NRd, an oxygen atom, a sulfur atom, or a selenium atom,
Ra, Rb, Rc, and Rd each represent a hydrogen atom or a substituent,
R1 represents a halogen atom or a group represented by Formula (W), and p is an integer of 0 to 2,
n represents 1 or 2,
* represents a bonding site,
*-L-T Formula (W)
in Formula (W), L is a single bond, or a divalent group represented by any one of Formulae (L-1) to (L-25), or a divalent group formed by bonding two or more divalent groups represented by any of (L-1) to (L-25),
T represents a hydrogen atom, a halogen atom, or a cyano group,
* represents a bonding site,
in Formulae (L-1) to (L-25), the wavy line portion represents a bonding site to a ring structure represented by Formula (1) to (3), and (8) to (10), or a bonding site to * of a divalent group represented by any one of Formulae (L-1) to (L-25),
* represents a bonding site to T, or a bonding site to a wavy line portion of a divalent group represented by any one of Formulae (L-1) to (L-25),
in Formulae (L-1), (L-2), (L-6), and (L-13) to (L-24), RA represents a hydrogen atom or a substituent,
in Formula (L-13), m is an integer of 1 to 4, m in Formulae (L-14) and (L-15) is an integer of 1 to 3, and m in Formulae (L-16) to (L-20) is 1 or 2, and m in Formula (L-22) is an integer of 1 to 6,
in Formulae (L-20) and (L-24), RN represents a hydrogen atom or a substituent, and
in Formula (L-25), Rsi represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group.

17 more elements

An organic semiconductor film comprising:

a compound represented by Formula (1), a compound represented by Formula (2), and/or a compound represented by Formula (3), or a polymer having at least one structural unit represented by any one of Formulae (8) to (10),
in each formula, X1 represents a nitrogen atom or CRa, rings A and B each are a 5-membered or 6-membered aromatic heterocyclic ring having a nitrogen atom as a ring-constituting atom or a fused ring including a 5-membered or 6-membered aromatic heterocyclic ring having a nitrogen atom as a ring-constituting atom,
Y1 represents an oxygen atom, a sulfur atom, CRb2, or NRc,
V1 represents NRd, an oxygen atom, a sulfur atom, or a selenium atom,
Ra, Rb, Rc, and Rd each represent a hydrogen atom or a substituent,
R1 represents a halogen atom or a group represented by Formula (W), and p is an integer of 0 to 2,
n represents 1 or 2,
* represents a bonding site,
*-L-T Formula (W)
in Formula (W), L is a single bond, or a divalent group represented by any one of Formulae (L-1) to (L-25), or a divalent group formed by bonding two or more divalent groups represented by any of (L-1) to (L-25),
T represents a hydrogen atom, a halogen atom, or a cyano group,
* represents a bonding site,
in Formulae (L-1) to (L-25), the wavy line portion represents a bonding site to a ring structure represented by Formula (1) to (3), and (8) to (10), or a bonding site to * of a divalent group represented by any one of Formulae (L-1) to (L-25),
* represents a bonding site to T, or a bonding site to a wavy line portion of a divalent group represented by any one of Formulae (L-1) to (L-25),
in Formulae (L-1), (L-2), (L-6), and (L-13) to (L-24), RA represents a hydrogen atom or a substituent,
in Formula (L-13), m is an integer of 1 to 4, m in Formulae (L-14) and (L-15) is an integer of 1 to 3, and m in Formulae (L-16) to (L-20) is 1 or 2, and m in Formula (L-22) is an integer of 1 to 6,
in Formulae (L-20) and (L-24), RN represents a hydrogen atom or a substituent, and
in Formula (L-25), Rsi represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group.

15 more elements

A compound represented by any one of Formulae (1) to (3) or a polymer having at least one structural unit represented by any one of Formulae (8) to (10),

in each formula, X1 represents a nitrogen atom or CRa, rings A and B each are a 5-membered or 6-membered aromatic heterocyclic ring having a nitrogen atom as a ring-constituting atom or a fused ring including a 5-membered or 6-membered aromatic heterocyclic ring having a nitrogen atom as a ring-constituting atom,
Y1 represents an oxygen atom, a sulfur atom, CRb2, or NRc,
V1 represents NRd, an oxygen atom, a sulfur atom, or a selenium atom,
Ra, Rb, Rc, and Rd each represent a hydrogen atom or a substituent,
R1 represents a halogen atom or a group represented by Formula (W), and p is an integer of 0 to 2,
n represents 1 or 2,
* represents a bonding site,
*-L-T Formula (W)
in Formula (W), L is a single bond, or a divalent group represented by any one of Formulae (L-1) to (L-25), or a divalent group formed by bonding two or more divalent groups represented by any of (L-1) to (L-25),
T represents a hydrogen atom, a halogen atom, or a cyano group,
* represents a bonding site,
in Formulae (L-1) to (L-25), the wavy line portion represents a bonding site to a ring structure represented by Formula (1) to (3), and (8) to (10), or a bonding site to * of a divalent group represented by any one of Formulae (L-1) to (L-25),
* represents a bonding site to T, or a bonding site to a wavy line portion of a divalent group represented by any one of Formulae (L-1) to (L-25),
in Formulae (L-1), (L-2), (L-6), and (L-13) to (L-24), RA represents a hydrogen atom or a substituent,
in Formula (L-13), m is an integer of 1 to 4, m in Formulae (L-14) and (L-15) is an integer of 1 to 3, and m in Formulae (L-16) to (L-20) is 1 or 2, and m in Formula (L-22) is an integer of 1 to 6,
in Formulae (L-20) and (L-24), RN represents a hydrogen atom or a substituent, and
in Formula (L-25), Rsi represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group.

14 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/588,574Filed 30 Sep 2019 · continuation
Priority: JP JP2017-07181831 Mar 2017
Published: US 2020/0028092 A123 Jan 2020
Granted: 3 Aug 2021
Term ends: Not estimatedThe source records don’t support an estimate.

Classification36 codes

C07D 517/22
Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero…
B05D 5/12
Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures: to obtain a…
C07D 495/16
In which the condensed system contains three hetero rings: peri-condensed systems
C07D 495/22
Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms: in which the…