Hydrogen barrier agent, hydrogen barrier film forming composition, hydrogen barrier film, method for producing hydrogen barrier film, and electronic element

Patent metadata

Field	Value
Publication number	US-11142629-B2
Application number	US-201916362344-A
Country	US
Kind code	B2
Filing date	Mar 22, 2019
Priority date	Mar 28, 2018
Publication date	Oct 12, 2021
Grant date	Oct 12, 2021

Abstract

A hydrogen barrier agent capable of imparting hydrogen barrier performance to various materials; a hydrogen barrier film forming composition including the hydrogen barrier agent; a hydrogen barrier film including the hydrogen barrier agent; a method for producing a hydrogen barrier film, which uses the composition; and an electronic element provided with the hydrogen barrier film. A salt compound having a specific structure including an imidazolyl group is used as the hydrogen barrier agent. The composition is prepared by blending the hydrogen barrier agent into the base material component. The hydrogen barrier film is formed using the hydrogen barrier film forming composition.

First claim

What is claimed is:

1. A hydrogen barrier agent comprising a compound represented by the following formula (1):

wherein X m+ represents an m-valent counter cation,
the counter cation is an acyclic or cyclic nitrogen-containing aliphatic cation, a nitrogen-containing aromatic cation, or a metal cation,
the acyclic or cyclic nitrogen-containing aliphatic cation comprises a cation represented by any one of the following formulas (2) to (4) and (14) to (16):

wherein R 11 to R 14 each independently represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, or an optionally substituted heterocyclic group,
at least one selected from R 11 to R 14 is an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, or an optionally substituted heterocyclic group, and at least two selected from R 11 to R 14 may link together to form a ring,
(R 21 ) 2 N + ═C(NR 22 2 ) 2   (3)

wherein R 21 each independently represents a hydrogen atom, an alkyl group, or a cycloalkyl group, R 22 each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a —C(═NR 23 )—NR 23 2 , wherein three R 23 each independently represents a hydrogen atom, an alkyl group, or a cycloalkyl group, or ═C(—NR 24 2 ) 2 , wherein four R 24 each independently represents a hydrogen atom or an organic group,

wherein R 31 each independently represents a hydrogen atom or an organic group, and s represents an integer of 2 or more and 6 or less,

R H each independently represents a hydrogen atom or an alkyl group, R 53 and R 55 each independently represents an alkyl group or a cycloalkyl group, R 54 represents an alkylene group, a cycloalkylene group, or a divalent group obtained by linking thereof, R 56 represents an alkylene group, R 53 to R 56 each independently may be substituted with a halogen atom, a cyano group, or a nitro group, at least two R 53 may be bonded to each other to form a ring, R 53 and R 54 may be bonded to each other to form a ring, and two R 55 may be bonded to each other to form a ring,
the nitrogen-containing aromatic cation comprises a cation represented by any one of the following formulas (5) and (7) to (13):

wherein R H each independently represents a hydrogen atom or an alkyl group, R 41 , R 45 , R 46 , R 47 , R 48 , R 50 , R 51 , and R 52 each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group, a cycloalkyl group, an alkenyl group, or an alkynyl group, R 42 and R 49 each independently represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, or an alkynyl group, R 41 to R 52 each independently may be substituted with a halogen atom, a cyano group, or a nitro group,
R 41 and R 42 may be bonded to each other to form a ring, at least two R 41 may be bonded to each other to form a ring, at least two R 45 may be bonded to each other to form a ring, at least two R 46 may be bonded to each other to form a ring, at least two R 47 may be bonded to each other to form a ring, R 48 and R 49 may be bonded to each other to form a ring, at least two R 48 may be bonded to each other to form a ring, at least two R 50 may be bonded to each other to form a ring, at least two R 51 may be bonded to each other to form a ring, and at least two R 52 may be bonded to each other to form a ring,
wherein the metal cation is a cation of a metal atom selected from the group consisting of alkali earth metal elements, hafnium, metal elements belonging to Group 14 excluding carbon and silicon, metal elements belonging to Group 15 excluding nitrogen, phosphorus, and arsenic, metal elements belonging to Group 16 excluding oxygen, sulfur, selenium, and tellurium, and semimetal elements, and a cation of an atomic group comprising any one of the above metal atoms,
and R 1 represents an optionally substituted aromatic group, R 2 represents an optionally substituted alkylene group, R 3 represents a halogen atom, a hydroxyl group, a mercapto group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a sulfonate group, a phosphino group, a phosphinyl group, a phosphonate group, or an organic group, m is an integer of 1 or more, n is an integer of 0 or more and 3 or less, and R 2 may be bonded to R 1 to form a cyclic structure.

2. A hydrogen barrier film forming composition, comprising a base material component (A), and the hydrogen barrier agent (B) according to claim 1 .

3. The hydrogen barrier film forming composition according to claim 2 , wherein the base material component (A) includes an alkali-soluble resin (A1) a photopolymerizable compound (A2), and a photopolymerization initiator (C).

4. A hydrogen barrier film comprising the hydrogen barrier agent (B) according to claim 1 .

5. A hydrogen barrier film comprising a cured product of the hydrogen barrier film forming composition according to claim 3 .

6. A method for producing a hydrogen barrier film, the method comprising:
forming a coating film by applying the hydrogen barrier film forming composition according to claim 3 on a substrate; and
exposing the coating film.

7. An electronic element comprising a passivation film and the hydrogen barrier film according to claim 4 .

8. The electronic element according to claim 7 , further comprising a thin film transistor (TFT).

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Hikida Jiro
• Someya Kazuya
• Misumi Koichi
• Shiota Dai

Classifications

• H10D30/67

  Thin-film transistors [TFT] {(Stacked nanowire, nanosheet or nanoribbon FETs H10D30/501)} · CPC title

• C07D219/02

  with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C07D487/08

  Bridged systems · CPC title

• G03F7/16

  Coating processes; Apparatus therefor (applying coatings to base materials in general B05; applying photosensitive compositions to base for photographic purposes G03C1/74) · CPC title

• C07F9/6506

  having the nitrogen atoms in positions 1 and 3 · CPC title