JPH03123763A - Infrared absorbing compounds and optical recording media using them - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

Detailed Description of the Invention [Field of Industrial Application] The present invention relates to an infrared absorbing compound and an optical recording medium using the same. This invention relates to an external absorption compound and an optical recording medium using the same.

[Prior Art] Generally, optical discs and optical carts have optically detectable small (
For example, about 1 pm), the pits can be in the form of spirals or circular and linear tracks to store high density information. To write information on such optical discs and optical carts, a focused laser is scanned over the surface of the laser-sensitive layer, and only the surface irradiated with this laser beam forms pits, and the bits are arranged in a spiral or circular shape. It is formed in the form of a straight track. The laser-sensitive layer can absorb laser energy and form optically detectable pits. For example, in heat mode recording, the laser-sensitive layer absorbs thermal energy and creates small depressions at that location by evaporation or melting. (bit) can be formed. In another heat mode recording method, absorption of irradiated laser energy can form bits with optically detectable density differences at the locations.

For example, by using an organic dye thin film as a recording layer with high reflectance, the optical contrast of recording bits can be set high.

As organic dye thin films, polymethine dyes, azulene dyes, cyanine dyes,
When pyrylium pigments are used, metallic luster (reflectance lO
A light-absorbing/reflecting film exhibiting a light absorbing/reflecting film of 50%) is obtained, and an optical recording medium capable of laser recording and reflective reading is obtained. In particular, use of a semiconductor laser with an oscillation wavelength of 600 ns and 900 ns as a laser light source has the advantage that the device can be made smaller and lower in cost. However, organic dye thin films.

In general, there has been a problem in that recording/reproducing characteristics and storage stability deteriorate due to material change resistance when exposed to heat and light.

[Problem 8 to be solved by the invention] The present invention has been made in view of the above-mentioned prior art, and its purpose is to provide a material that has a large absorption region in the infrared region and is soluble. The object of the present invention is to provide a good infrared absorbing compound.

Another object of the present invention is to provide an optical recording medium in which the novel infrared absorbing compound of the present invention is used in an optical recording medium that has significantly increased durability and tip stability during repeated reproduction. .

[Means for Solving the Problems] and [Operation] That is, the present invention provides an infrared absorbing compound represented by the following general formula CI] or general formula [II], and an infrared absorbing compound represented by the general formula [I] and/or the general formula An optical recording medium characterized by having an organic dye thin film containing an infrared absorbing compound represented by [11].

(In the formula, R, to R, represent a hydrogen atom, a halogen group, or a monovalent organic residue. R, to R8 may be different or the same. Also, R, and R2, R3 and R,
, a combination of R8 and R6 and R7 and R, forming a 5-membered ring.

A 6-membered ring or a 7-membered ring may be formed.

A represents C [or CC], B represents [(or C], the aromatic ring may be substituted with a lower alkyl group, a lower alkoxy group, a halogen group or a hydroxyl group) (e represents an anion, ) In the above general formula [I] and general formula [111], R
3-R6 represents a hydrogen atom, a halogen group, or a monovalent organic residue. Examples of halogen groups include fluorine, chlorine,
Examples of monovalent organic residues such as bromine and iodine include 1. Examples of alkyl groups include methyl group, ethyl group,
n-propyl group.

1so-propyl group, n-butyl group, 5ec-butyl group, 1so-butyl group, t-butyl group, n-amyl group, t-amyl group, n-hexyl group, n-octyl group, t
-octyl group, and other alkyl groups, such as substituted alkyl groups, such as 2-hydroxyethyl group, 3-hydroxypropyl group, 4-hydroxybutyl group, 2-acetoxyethyl group, carboxymethyl group,
2-carboxyethyl group, 3-carboxypropyl group,
Examples of alkenyl groups such as methoxyethyl group, ethoxyethyl group, and methoxypropyl group include vinyl group, propenyl group, butenyl group, and pentenyl group.

Examples of aralkyl groups such as hecanyl group, heptenyl group, and octenyl group include benzyl group.

p-chlorobenzyl group, p-methylbenzyl group.

2-phenylmethyl group, 2-phenylpropyl group, 3-
Examples of the alkynyl group include a phenylpropyl group, an α-naphthylmethyl group, and a β-naphthylethyl group, such as a propargyl group and a butynyl group.

These include pentynyl group and hexynyl group.

R3-R6 may be different or the same.

Also, R, and R,, R3 and R4, R5, R6, and R7
and R8, a substituted or unsubstituted 5-membered ring, 6
A 5-membered ring or a 7-membered ring may be formed; the 5-membered ring is a pyrrolidine ring, and the 6-membered ring is a piperidine ring.

Examples of the morpholine ring, tetrahydropyridine ring, and 7-membered ring include a cyclohexylamine ring. These rings may be the same or different.

> (e is chloride ion, bromide ion, iodine ion, perchlorate ion, nitrate ion, benzenesulfonate ion, P-toluenesulfonate ion, methyl sulfate ion, ethyl sulfate ion, propyl sulfate ion, tetrafluoroborate ion, tetraphenylborate ion, hexafluoroline salt ion, benzenesulfinate ion, acetate ion, trifluoroacetate ion, propionacetate ion, benzoate ion, oxalic acid salt ion, succinate ion, malonate ion, oleate ion, stearate ion,
Citrate ion, -hydrogen diphosphate ion, dihydrogen-
Phosphate ion, pentachlorostannate ion, chlorosulfonate ion, fluorosulfonate ion, trifluoromethanesulfonate ion, hexafluoroarsenate ion, hexafluoroantimonate ion,
Represents anions such as molybdate, tungstate, titanate, and zirconate.

The method for producing an infrared absorbing compound of the present invention is described in US Pat. No. 3,251,881, US Pat. No. 1,575,871, US Pat.
For example, it can be produced by the following process.

■2N−■−N12+ 41+No2−−→CIItN
%N-■-N(-◎→11.]2 After the amino compound obtained by the above Ullmann reaction and reduction reaction is substituted by selective substitution, for example, by alkylation, alkenylation, aralkylation, or alkynylation, The final product can be obtained by an oxidation reaction.

When R1 and Ra are asymmetric, it is necessary to perform this alkylation in multiple stages, and from the viewpoint of cost, it is preferable that Ro and Ra are the same.

Next, specific examples of the infrared absorbing compound represented by the general formula [I] or the general formula [nl according to the present invention will be given. For simplicity, A is 1 and ×0 is CI! At 04°, I
'1. , R2, R3, R, are ethyl groups, R'i+R6
+R,, When R,1 is a methyl group.

Cl13. CL (:ll:l, Cll:+).

Mata, B Ka () Ql: Te, 2x0 Ka2 Bre Te, RI
When a 5-membered ring is formed by the combination of R2, RY and R4, R5 and R6, and R7 and R8, Cσ Br, CH2G + 12CI (2Cilt CH
2CH*CHzCHtCH, CH2CH2C112C1
It is expressed as 12G 112 C82C112.

In addition, in the present invention, R1-R8 are RI+R*,
Rs+ R4+ Ran Ran R? and R6 are shown.

Compound No., A [IJ-(11) CHmi[I]-(I1)σ Circle-(13)σ [I 1-(14)σ River-(15) Cc ) x R, 112 CIl:l+0.3n-CIl(zs,n-C+zll
zsCjl! 04C2+1. cH=cl-12,C,1
LCH=CI+.

(J!0. (:H,O(:11., C2H4CH
.

SbFg C2H,0C)1. , C21LOfl:
Island NO30C2Hs, 0C211s SbFa C112CH2C11, (:11□R:
1R4 n-C+2Hts+n-C+211zsCJ, Cll=
CH,,C2H4CH-C:H.

(:H2QC:H,3,C1,0(:113C2H,O
C)+3. C21140CH3n-C3Ht, n-C3
Ht CH2Cl2. C112CH2 R2H.

n-ClJ2s+n-ClJ12% C21L(:H-CIl, ,C2H4C)l-C)I
.

C bird OC1,, CH20CH Yu (21140C1++, C2) IJ(:H30CzHs
, OC+dls CI2C1l, (:82C11°R?R8 1-(:12H26,1l-C12112sCzl14
C) l-CL, C2H4CH=C1kCH20CH3,
CH□O(:fl+ C2H40CH:+, CJ40CH3 n-C3Hy, n-(:311y CH2CII□Cl2C112 [I]-(la) [I]-(I1) σ r C1) 0°CH, C1120C)l, C1l .

03 C1l□CH□CH□C1l□CH2 C) I2C820CIl□CI4□ (:H2Cl1□CI(□CI(*CH2CH□CH*
0CHaCHt C11tel(2(:HzCH2C11gCH2CH2
0(:11□CI+□ CH, fl:H, C112CII2fl:+12 Compound No-A [1]-(29)σCβ04 [I 1-(30) CcASF6 R,R.

C, H4CR, C6114CII CJi, +1:1lls R, It.

C, 114Cj7. C6H, CJ CJIs, CJs R.S.R.

C, l amount 4Cj', CaHnC1' C2H5, C211s R’yRa C, 04C1', C6H4Cβ Czlls, Cjls [Il-('12) [I]-(33) [I]-(:l14 [I] - (35) C [ σ σ σ BF.

B" C.R.O.

SbF.

n-C, H,, n-CJ.

CJ4CR-C21LCR C)l-C(CH3) CII□C((:11.)2C
I12Cj), CJi n-C11lt, n-C3H7 C, H, CR, C21+4C1I CH Tomi C (C113) C112C (CIl:1) 2C1
12CR,CR n-C5+1t,n-C:+l1t CJ4CR9CzH<CjI C11-C(CI-13)CH2C(CHi3)tcl
l□C2H,,C,1Is CH*CI! zCI12(1:1la CaH4(:j', (:J4C1 (:1IIIC(CI(3)Cll□(:(C113)
2C112CJs, CJs compound￥＠No.

[I’]-(1) [I’]-(2) [I’1-(3) [I’]-(5) [1']-(6) [f'1-(7) [I’]-(8) [I’1-(9) C.J. 0 construction 0 construction C1’O.

CRO4 SbF.

R+R* CIh, C1(3 CtH5, CJs OC*HS, OC*H5 C.J. C.J. CC [ C.J. C.J. C.R.O.

SbF6 CRO4 SbF.

n-CJ, , n-(:Jy iso-C3Ht+1so-C3Hy OC,H,,OC,)I.

C11□CH=CII*, CIl□CH-C)12G2
1LCII-CHi, Cl2CII-(:HzR,R
4 C113, CHi CJs, CJs OCJs, 0C2Hs CHi3 H*CHCJs n-et al.) l? I n-C3Ht iso-C3Ht, 1so-C, fl.

OC,119,OC,l19 CI1gCI=CI2. C) ltcH-(:ll*C,
H, CH-CIll, C2H, C11-CH.

"9 8R41 CH3, CH3 C211seCJq OC*Hs, 0C2H! 1 C)1. , CH3 n-C,3Ht+n-C5Ht iso-C3H7,1so-C311tOC41 place 9,
0C4H9 CIl, Cl1-C)12, Cl2CII-C112
G21LCII-C1l*, C21LCII”Cl1
tn-C,H,,n-C,Il.

R,R.

CHi3. CH3 C211s, CJ5 0C2HS, 0C2H.

C1,, Cl5 n-C311t, n-C31+7 iso-C:Jlt, 1so-GullyO(:4
119,0C4119 CH2(:H-CIl,,CH,(:ll-C112C
,114CH-C112,C,114CII-CI12
n-c411s, n-CJIs 482- Compound No.

R, R2 Compound no.

R,R.

[11]-(3) 〔Ku bFa OCH:1. OCH:1 R, 11° n-CJ, , n-C:lH.

C, H, C12, C, H4CR C2t15. CJs R,R.

n-(:3+1y　,n-C,117 C6H4C4), C,H4C1' C211s, Cjls R? R6 n-CJ,, n-CJy C6n, cp, c6u4ciI C211,, C2+1S R,R.

(::+lly, n-CJt Hs, CtHs OCR+, QC)+3 C,H,,n-C,H.

Q-C:lH? l　1so-CzT.

,,CH Yu KoH,,0C3H.

zcll-C)12. Cll2Cll=C1122CI
+=(:11., CH2Cll-CH2C14112
9+n-C141129 R13R.

n-c:11? , n-C1Ht C2Hs, CtHs OCHi, 0Cfl+ n-C, Il,, n-C4) 19 iso-CIHy, 1so-C311yCH,, CH
3 0CyuH,,OC:ll+7 CI(telI=ctlz, CIl□C8-C112
CI1. Cl1=CI+, ,CI(□C11=11
゜n-Ct<H29+11-(+J12sJa n-C1+1., n-C,H.

C,)1. , C21+.

0(l(3,QC)!3 n-C4H9,n-CJIs iso-C=Hy, 1so-Cl1=CI+3.CI
+.

OC*Ht, 0C3H? CH, C11-CIl□, CI+2 (:ll=CH□C
82 CIl=CH,, CIl□CH=CI.

n-C141129+n-Cl41129484- Compound no.

B [11j-(11) α bFg R,R.

C, +14 (:ll-C11□, C, ILCll-CI
I23R4 Ca)14cH-CH*, CJ<Cll”CH□sRg Cal<Ct(=CHa, CJ(4C1l-(:112
R? R6 C2■4CI+=CIIz, C6H4Br-111(z
[11]-(13) [II]-(14) [II]-(15) [111-(16) [ku[kuα α [II]-(18) [11]-(19) [teα 5b)r.

cI! o.

03 Cβ04 OC2H5,0CzHs CF3. C.F.

C211,0C113,(:31(60C113G2+
LOG, 11. , C21140C211°C11be)
) So: + 0Csll lt, 0CsHt tI
CJIJr, Cs1lJrOCzHs, 0C
JIs CF, , CF.

C+H60CIIz, C+1I60(:HzCtlln
OC2f(a, Czl140CjlsOCsH1t,
0Csll+ + CaHJr, Ca11. Br 0CJ (5,OG2+1s CF,,CF3 C,+160CH3,C,)160cl13CzlLO
Ctlls, CJLOCz)Isiso-C:+To
, 1so-CJyOCaH+ l, 0CaHII C6114Br, C6H4Br 0CJsIOCJs CFff, CF:1 C+1I60CHi, C:+HsOCII+C2114
0G21+5, C21140C211Siso-(:
J? , 1so-C311yOC511t s , 0C
sf(+ 1CaHJr, C5HJr Compound No, B [old-(20) @ cI!o4 [111-(21) Cc, Cf,.

tRt CH, -C, HS, CH2-C6HS (:F1a(:miCH,CH2C=CHRJ< CH*-CaHs, Cll□-G, )I.

C1l□CmiCl,CJ(□CmiCH R,5Ra CH2-Ca) Is, CH2-CaH,.

(:1I2CmiCH,C)1. (:mi(JlR,R.

CH2-C61(,, CIl□-Cr, HsCH2CmiCH, Cll2CmiC11 CH2CH, Cl1C1, CH.

C112C112C112C112C112[■]-(
24) [rI]-(25) α Br SbF.

CH2CH20CHzCHt CHiCI(tcHac)lx(:HtelltCIl
□CH,0C11,C11゜Cl2CI'1zCH2CH*CHaCH2(J12C
1120CH,CH2 Cl1□C1,CH,CIl□co2cutCH*C8
20CH2CI2 CH, CIl□C) I2G412Ct12CII2CI
ICII□C112CI+ 11, I+ 485- Compound No.

[n'1-(1) [II’1-(2) [II’1-(3) [11’1-(4) [11’1-(5) [■’]-(6) [11’1-(7) [II’1-(8) [n'1-(9) [11'1-(10) O.C. C.I. C.I. to C to C C [( to C C [[ CCJ:.

C.I. CJI04 CJI04 SbF.

5F6 Cf.

r CI! O.

CJI04 SbF6 ■ Jt n-CJIy, n-C3lIt CJ(S, CJS OCH:+, OCHi n-CJlg, n-C411g in-C41l, 1so-CIlltC113, C
H.

OC:dly, OCJt CHzCIl-Ctlg, C) IzCI-CHzCI
l2(:II=CI+,,C1(2CltoCH□n-C
14H2s+n-CIJlis R3R.

n-C3Hy, n-CJt C2 juice! +C2)! ! 0CHz, 0CH3 n-(:J(,,n-CJI.

1so-CJy+ 1so-CJt CH3, CJI3 0CsHt, 0C3Ht (:HzCH=CHi, Cl2C)I-C)ItC1l
□Cl1=CHt, C)It(:H=CIIzn-
CIJIzs+n-C+Jzs 5Ra n-CJt on-CJy CJs, CJs OCH3,0CH3 n-C4■s, n-C,l(.

1so-C311y, 1so-C3HyCH3,C
H3 0C3H,,OC! +1°CHzCH-CH*, CHzCIl-C)Isctt
, cu=cu□, CH2Cl1=CIlin-C441
1*s, n-n-C141l2? Ra n-C3Ht, n-C3Ht C*H! 3. CtHs OC11□0C)I.

n-CnHs, n-CJIs iso-C, H, 1so-C31+.

CJI3. CJI3 OC31, OCJy C11gC11=CII*, CIItCH-C)12C
)1. CI (Snow (J12.Cl2CII-C) ltn-
C14H2s+n-(+Jlts Compound No.

R,R.

R2H.

CHi-CaHs, CHt-CsllsCH, Cmic
tt, ctt2c=c.

CH2Cll2CH, CHiCH1 CH2GHzOCH*C1l□ CIl□CH*CHtCHtCHtCII*5Rs C1la-Ca)Is, CHi-CJIsCIIaC=
CH,CH2C=C)l CH*CHtCtlaCH*CH2 CH2CIItOCH*CI+1 CH,C1,C1,C)12CIIC)ItR? R.

Cut-C6115, (:H2-C,ll5CH*C=
Cl1. CHiC=CII CHzC+1gCH*Cl1tCH2 CII□C120Ctl*CHt C+1. CII□CHzCIIaCIaCI12 Compound No.

B 11, R2 J4 5R6 R? R6 CI(20cl13.CH20CH3 0C11□0CH3 C, H, Cl1-CH□, C, H, CH-CI(.

CI+20CH3, CI□OCR.

0C1l*, QC)l:+C,H,CH-CH,,C,116C)I-CI2CH
20CII+, (JIzOCHzn-C2Ht,n
-C3Ht CJ6C11-CH□C,ll6CII=C112n-
C,,)It, n-C=Ht C1(=C(C)1z)CIIzC(Cl13)zcl
l□n-C:+lly, n-C311t OH-C(CH3)CH2C((:Il+)tcHzn
-ClHt, n-CJy CII=C(C)I3) CII□C(CH:+) zc
H* The aminium salt compound or diimonium salt compound exemplified above has a maximum absorption wavelength of 900 nm or more, and has a large absorption peak with an extinction coefficient ranging from several tens of thousands to about 1000 yen.

In addition to being used as materials for optical recording media, such infrared absorbing compounds are used in heat insulating films, sunglasses, and the like.

Further, the infrared absorbing compound of the present invention can be used by being included in an organic dye thin film of an optical recording medium.

As the near-infrared absorbing dye that forms an organic dye thin film that is used in combination with these infrared absorbing compounds as an optical recording medium, commonly known dyes are used, such as cyanine dyes, merocyanine dyes, Croconium pigment, squalium pigment.

These include azulenium pigments, polymethine pigments, naphthoquinone pigments, pyrylium pigments, and phthalocyanine pigments.

The amount of the infrared absorbing compound consisting of the aminium salt compound of the general formula [I] and/or the diimmonium salt compound of the general formula [R1] added to these dyes is 1% to the recording layer based on the total solid content. ~60% by weight, preferably 5
~40% by weight, more preferably 10-30% by weight is suitable.

In addition to these compounds, a binder may be contained in the recording layer consisting of an organic dye thin film. Examples of the binder include nitrocellulose, cellulose phosphate, cellulose sulfate, cellulose acetate, cellulose propionate,
Cellulose acetate, cellulose myristate, cellulose parimitate, cellulose acetate/propionate, acetic acid/cellulose
Cellulose esters such as cellulose acetate, cellulose ethers such as methylcellulose, ethylcellulose, propylcellulose, butylcellulose, vinyl resins such as polystyrene, polyvinyl chloride, polyvinyl acetate, polyvinyl butyral, polyvinyl acetal, polyvinyl alcohol, polyvinylpyrrolidone, Copolymer resins such as styrene-butadiene copolymer, styrene-acrylonitrile copolymer, styrene-butadiene-acrylic nitrile cobosomer monovinyl chloride-vinyl acetate copolymer, polymethyl methacrylate, polymethyl acrylate, polybutyl acrylate, polyacrylic acid, Acrylic resins such as polymethacrylic acid, polyacrylamide, and polyacrylonitrile, polyesters such as polyethylene terephthalate, poly(4,4'
-Isofuropylidene diphenylene-1,4-cyclohexylene dimethylene carbonate), poly(ethylenedioxy-3,3'-phenylene thiocarbonate),
Poly(4,4'-isopropylidene diphenylene carbonate coated terephthalate), poly(4,4'-isopropylidene diphenylene carbonate), poly(4,4'-isopropylidene diphenylene carbonate),
Polyarylate resins such as 4'-5ec-butylidene diphenylene carbonate), poly(4,4'-isopropylidene diphenylene carbonate-protoxyethylene), polyamides, polyimides, epoxy resins, phenolic resins ,polyethylene,
Polyolefins such as polypropylene and chlorinated polyethylene can be used.

Further, the recording layer may contain surfactants, antistatic agents, stabilizers, dispersible flame retardants, lubricants, plasticizers, and the like.

Further, an undercoat layer may be provided between the recording layer and the substrate, and a protective layer may be provided on the recording layer.

As an undercoat layer, it can be used to impart solvent resistance, improve reflectance, or improve repeat playback.

The protective layer is used for protection from scratches, dust, dirt, etc., and for environmental stability of the recording layer.

The materials used for these are mainly inorganic compounds, metals, or organic polymer compounds. As an inorganic compound, 1, for example, 5in2. MgF2. Sin, Tj02
＋ZnO, TiN, SiN, etc.; Examples of metals include Zn.

Cu, Ni, Aj), Cr, Ge, Se,
Cd, etc., and organic polymer compounds such as ionomer resins, polyamide resins, vinyl resins, natural polymers, epoxy resins, and silane coupling agents can be used.

As the substrate, plastics such as polyester, polycarbonate, acrylic resin, polyolefin resin, phenol resin, epoxy resin, polyamide, polyimide, glass, or metals can be used.

Organic solvents that can be used during coating should be in a dispersed state or
Or, depending on the dissolved state, alcohols such as methanol, ethanol, isopropanol, and diacetone alcohol, ketones such as acetone, methyl ethyl lactone, and cyclohexanone, N, N-
Amides such as dimethylformamide and N,N-dimethylacetamide, sulfoxides such as dimethyl sulfoxide, ethers such as tetrahydrofuran, dioxane, and ethylene glycol methyl ether, esters such as methyl acetate, ethyl acetate, and butyl acetate, chloroform, Aliphatic halogenated hydrocarbons such as methylene chloride, dichloroethylene, carbon tetrachloride, trichlorethylene, and benzene.

Aromatics such as toluene, xylene, monochlorobenzene and dichlorobenzene, or aliphatic hydrocarbons such as n-hexane and cyclohexanoligroin can be used.

Coating methods include dip coating method, spray coating method, spinner coating method, beat coating method,
Wire bar coating method.

This can be carried out using a coating method such as a blade coating method, a roller coating method, or a curtain coating method.

The thickness of the recording layer formed using such a solvent is 50
An appropriate range is A to 100 μm, preferably 200 A to 1 μm.

[Example] Next, examples of the present invention will be described.

Synthesis Example 0 - 0.1 mol of phenylenediamine, 0.44 mol of p-nitrochlorobenzene, 0.23 mol of charcoal-free potassium, and 2 parts (by weight) of copper powder were refluxed under stirring in 130 parts of dimethylformamide for 4 days. went. After the reaction, the reaction mixture was passed through the mouth, and the raw material was thoroughly washed with dimethylformamide, water, and acetone, and then dried.

Reddish brown tetrakis(p-nitrophenyl)-2,3-
26 parts of phenylenediamine were obtained.

Add 25 parts of the compound obtained above into an autoclave together with 2 parts of 95 parts of dimethylformamide palladium-carbon hydrogenation catalyst, and apply hydrogen gas at 5.0 g/cm2 to stop hydrogen absorption at 90°C to 100"C. Stir until

After the reaction, the reaction solution was passed through the mouth, washed with dimethylformamide, and then poured into 340 parts of ice water. After stirring for a while, the precipitate was taken out. Recrystallize with ethanol dimethylformamide mixed solvent to obtain tetrakis (
p-aminophenyl)-2,3-phenylenediamine 1
I got 0 copies. Purity was measured by high performance liquid chromatography and found to be 97.7%.

Synthesis of compound No. [I]-(5) Above amino compound 3
The mixture was heated and stirred with 18 parts of dimethylformamide, 0.7 parts of anhydrous sodium bicarbonate, and 3.9 parts of n-propyl bromide at 100°C to 1:1O"C. After reacting for 36 hours, the reaction solution was poured into 100 parts of ice water. and extracted with ethyl acetate. After drying, it was purified with a silica gel column. The amount obtained was 3.1 parts. The N of the amino group was determined by infrared absorption analysis.
It was confirmed that absorption due to il stretching vibration disappeared.

0.9 parts of this compound was dispersed in 20 parts of acetone, and the equimolar amount of silver perchlorate was added while stirring. After reacting at room temperature for 1 hour, the precipitated silver was separated out, diluted with oral isopropyl ether and allowed to stand, and the precipitated crystals were taken out. The amount obtained was 0.8 parts.

Compound No. synthesized in this way, [I] −(
5) has an absorption maximum wavelength of 998 nm and an extinction coefficient of 31,00
It was a compound with a large absorption region in the infrared region of zero.

Compound No. Synthetic compound No. of n-(1),
21 parts of tetrakis(p-dipropylaminophenyl)-2,3-phenylenediamine used in the synthesis of [I]-(5) was dispersed in 20 parts of acetone, and 2 times the mole of perchloric acid was added under stirring. Added silver.

After reacting at room temperature for 1 hour, the precipitated silver was separated and diluted with oral isopropyl ether.

0.6 parts of precipitated crystals were taken out.

In the example explained above, the anion is perchloric acid, but if other anions are used, the desired compound can be easily obtained by using the corresponding silver salt.For example, Ag5bF, .

8gBF,, 8gso,, AgN0i, A
Silver salts such as g5O3C, H, CI, 1, Ag5O3CF3 can be used. In addition, it can also be obtained by electrolytic oxidation.

Synthesis Example 2 The O-phenylenediamine used in Synthesis Example 1 was
．． The reaction was carried out in the same manner as in Synthesis Example 1 except that cordiaminonaphthalene was used, and tetrakis(p-aminophenyl)
22 parts of -2,:l-diaminonaphthalene were obtained.

Synthesis of Compound No., [I']-(25) 4 parts of the amino compound obtained in Synthesis Example 2 were mixed at 100° with 25 parts of dimethylformamide, 1.2 parts of anhydrous sodium bicarbonate, and 4.2 parts of 2-methoxyethyl bromide. The mixture was heated and stirred at a temperature of 130°C to 130°C. After reacting for 36 hours, the reaction solution was poured into ice water and extracted with ethyl acetate. After drying, it was purified using a silica gel column. The amount obtained was 3.8 copies. The disappearance of absorption due to the Ni1 stretching vibration of the amino group was confirmed by infrared absorption analysis.

One part of this compound was dispersed in 20 parts of acetone, and the same mole of antimony hexafluoride was added under stirring. At room temperature 1
After reacting for a period of time, the precipitated silver was separated every day, diluted with oral isopropyl ether and allowed to stand, and the precipitated crystals were taken out. The amount obtained was 1.0 part. Also, the maximum absorption wavelength is 1
It was 054n■.

Compound No. Synthesis compound N of [U']-(23)
o, 0.5 part of the pyrroline compound obtained during the synthesis of [I'l-(25) was dispersed in 11 parts of acetone, and while stirring, 2 times the mole of silver perchlorate was added at room temperature for 1 hour. After the stirred reaction, the precipitated silver salt was separated, and the acetone was thoroughly washed with acetone. The acetone was distilled off from the solution, washed with water, and then dried under reduced pressure.

The yield was 0.4 part, and it was an infrared absorbing compound with a maximum peak at 11061n.

Next, examples will be described in which the infrared absorbing compounds represented by the general formulas [I] and [1] are used as optical recording materials.

Example 1 A 501L pregroove was provided on a polymethyl methacrylate (hereinafter referred to as PMMA) substrate with a diameter of 130 mm and a thickness of 1.2 L, and a polymethine dye (TR-820 manufactured by Nippon Kayaku Co., Ltd.) was placed on it. ) and the infrared absorbing compound N
o, [I]-(5) at a weight ratio of 80:20 to 1.2-
A solution dissolved in dichloroethane was applied by spin coating.
A recording layer of 00 A was provided. Spacers of 0.3 mm were sandwiched between the inner and outer sides of the medium thus obtained, and the medium was bonded to another PMMA substrate using an ultraviolet curable resin adhesive to obtain an optical recording medium having an air sandwich structure.

This was rotated at 1800 rpm, and using a semiconductor laser with a wavelength of 8300 cm, the recording power was 6 mW from the substrate side.
The 0th order was written at a recording frequency of 2 MHz, reproduced at a read power of 0.8 mW, and the C/N ratio was measured by spectrum analysis. Subsequently, the C/N ratio was measured after 10,000 readings and reproductions were performed.

Furthermore, l KW/m was added to the optical recording medium prepared under the above conditions.
A light resistance stability test was conducted by irradiating the sample with xenon lamp light of No. 2 for 100 hours, and the reflectance and C/N ratio were measured. The results are shown in Table-1.

Table 1 Example 2 On the same substrate as in Example 1, by the same method as in Example 1,
l-guaiazulenyl-5-(6'-t-butylazulenyl)-2,4-pentadienol perchlorate and the infrared absorbing compound No.

[11] A recording layer was formed using liquids of (8) in a weight ratio of 90:10.

The same test as in Example 1 was conducted using the optical recording medium thus obtained. The results are shown in Table-2.

Table 2 Actual Table 3 27,1555223,352 Examples 3 to 7 Optical recording media having the compositions shown in Table 3 were prepared in the same manner as in Example 1, and the same tests as in Example 1 were conducted. Table 4 shows the results.
Shown below.

1,5-Diguaiazulenyl-2,4-pentadienol perchlorate I'-1285: ts (p-diethylaminophenyl)-(p-methoxyphenyl)methylene-1-cyclopent-2-diru-3-( p-dimethylaminophenyl)-(p-ethoxyphenyl)carbonium perchlorate -34 90:10 1.5-bis(diethylaminophenyl)-1,5-diphenyl-2,4-pentadienol perchlorate -14 75 225 1.1'-dimethoxyethyl- :l, :1,3',3'-tetramethyl-2,2'-indotricarbocyanine perchlorate n'-2680: 20 7NK-1414 (Japanese photosensitive dye type ) -470:30 Comparative Examples 1 to 3 Optical recording media were prepared in the same manner as in Examples 1.2 and 5 except that the infrared absorbing compound used in Examples 1.2 and 5 was removed, evaluated. The results are shown in Table 4.

Table-4 27,1 25,9 25,3 35,1 32,0 22,7 22,0 22,1 29,6 21,8 26,0 7 1 13,2 4 27,4 6 1 14,0 5 26, 2 3 7 12, 8 1 Examples 8 to 11 A pregroove was formed on an OLED size 0.4 mm thick polycarbonate (hereinafter abbreviated as rPcJ) substrate by a heat press method, and the following coating was placed on it. A liquid obtained by mixing the organic dye and infrared absorbing compound shown in -5 in diacetone alcohol was coated by a bar code method, and then dried to obtain a recording layer of 850A. Furthermore, an optical recording medium having a close contact structure was prepared by laminating a 0.3 mm thick Olet-sized PC board on top of the film through an ethylene-acetate dry film by a hot roll method.

The optical recording medium of each example prepared in this manner was mounted on a stage driven in the X-Y direction, and a semiconductor laser with an oscillation wavelength of 830 nm was used to deposit the organic thin film recording layer from the PC substrate side with a thickness of 0.4 cm. , information was written in the Y-axis direction with a recording power of 4.0 mW and a recording pulse of 80 μsec, and was reproduced with a read power of 0.4 mW, and the C intensity, B→signal intensity of the recording part) was measured.

Furthermore, the same optical recording medium produced under the above conditions was used in Example 1.
A light resistance stability test was conducted under the same conditions as above, and the reflectance and contrast ratio were then measured. The results are shown in Table-6.

Actual Table-5 Example 8 1R-820 (Nippon Kayaku) ■-15 80: 20 Nyl)methylene-1-cyclopent-2-2-3-(p-dimethylaminophenyl)-(p-ethoxyphenyl)carbonium・Perchlorate 10 1,5-bis(dipropylaminophenyl)-1,5-diphenyl-2,4-pentagenol Perchlorate 1-2 90: 10 Phenyl)-2,4-pentagenol iodite Example 12 In Example 8, the infrared absorbing compound was 1-10 and 1-29 was 1
An optical recording medium was prepared and evaluated in the same manner as in Example 8, except that the ratio of :1 was used. The results are shown in Table-6.

Comparative Example 5.6 Optical recording media were prepared and evaluated in the same manner as in Examples 8 and 10, except that the infrared absorbing compound was removed in Example 8 and IO. The results are shown in Table-6.

Table 6 After initial light resistance test Example 8 14.6 Example 9 15.3 Example 10 15.6 Example 11 15.0 Example 12 14.4 Comparative example 5 14.8 Comparative example 6 15.9 0.63 12.4 0.64 1 piece, I O,6612,9 0,6113,4 0,6212,3 0,7010,8 0,6710,6 0,59 0,60 0,60 0,58 0,58 0,48 0,46 [Effect of the invention] As explained above, the infrared absorbing compound represented by the general formula [I] of the present invention has a large absorption region in the infrared region,
By breaking the linearity, solubility was also improved.

Furthermore, when the infrared absorbing compound is contained in an organic dye thin film and used as an optical recording medium, it has become possible to obtain an optical recording medium with significantly increased durability and light resistance stability during repeated reproduction. .

Claims (2)

[Claims] (1) An infrared absorbing compound represented by the following general formula [I] or general formula [II]. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [I] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [II] (In the formula, R_1 to R_8 represent a hydrogen atom, a halogen group, or a monovalent organic residue. R_1 ~R_8 may be different or the same. Also, R_1 and R_2
, R_3 and R_4, R_5 and R_6 and R_7 and R_
A combination of 8 may form a 5-membered ring, a 6-membered ring, or a 7-membered ring. A has ▲mathematical formulas, chemical formulas, tables, etc.▼ or ▲mathematical formulas,
There are chemical formulas, tables, etc. ▼, B indicates ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, and the aromatic ring is a lower alkyl group, a lower alkoxy group, a halogen group, or a hydroxyl group. may be replaced by X^■ indicates an anion. ) (2) An optical recording medium comprising an organic dye thin film containing an infrared absorbing compound represented by the general formula [I] and/or the general formula [II] according to claim 1.