JPH06100566A - Octakis@(3754/24)alkoxyphenyl)tetrapyrazinoporphyradine compounds and composition containing the same and capable of forming discotic liquid crystal phase - Google Patents

Abstract

PURPOSE:To provide a novel compound soluble in organic solvents and having a molecular aggregate-forming ability. CONSTITUTION:A compound of formula I (R is 1-30C linear alkyl, branched alkyl such as 2-ethyl-hexyl), and that of formula II (M is transition metal ion). For example, 5,6,5',6',6'',5'',5''.6'''octakis(4-dodesiloxyphenyl)tetrapyranosyl[2, 3-b: 2',3'-g: 2'',3''-1:2''',3'''-q]porphiradinado] copper (II) complex. The compound of formulas I on II is obtained from 2,3-dicyano-5,6-bis(4-n-dodesiloxyphenyl) pyrazine, etc.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a chemically stable side which is useful for the development of functional thin films, such as addition of a solvent to a tetrapyrazinoporphyrazine compound having an n-acceptor property, solubility in a solvent, and development of liquid crystallinity. The present invention relates to a compound to which a chain is added or a metal complex, and a composition containing the compound or the metal complex and capable of having a discotic liquid crystal phase.

[0002]

2. Description of the Related Art Tetrapyrazinoporphyrazine compounds are thermally and chemically stable blue dyes having a structure similar to phthalocyanine, and also as functional materials showing conductivity, photoconductivity, catalytic activity, etc. Are known.

[0003]

In general, these compounds can be synthesized relatively easily, but most of them are hardly soluble in a solvent, so that they are difficult to purify and characterize.
Even when used, it was limited to the dry method, which would complicate industrial equipment such as vacuum deposition and sputtering. Further, the tetrapyrazinoporphyrazine compound has less derivatives as compared with the phthalocyanine compound, which has been an obstacle to industrial application.

In order to solve the above-mentioned problems, the present inventors have introduced a phenyl group substituted with a long alkoxy chain as a side chain of a tetrapyrazinoporphyrazine compound, thereby making it soluble in various organic solvents. Focusing on the ability to form molecular aggregates.

[0005]

Means for Solving the Problems As a result of investigations on tetrapyrazinoporphyrazine derivatives, the present inventors have found that 5,6,5 ′, 6 ′ of the tetrapyrazinoporphyrazine ring,
Introducing a phenyl group having a long alkoxy chain represented by the following general formula (1a) or (1b) at the 4-position at the 5 '', 6 '', 5 '''and6''' positions. And a metal complex, a compound and a metal complex in which two long-chain alkoxy chains represented by the general formulas (2a) and (2b) are introduced at the 3 and 4 positions and a phenyl group is introduced, and physical properties thereof are obtained. The measurement was performed and the present invention was completed.

[0006]

[Chemical 1]

[0007]

[Chemical 2]

[0008]

[Chemical 3]

[0009]

[Chemical 4]

The outline will be described below. In the above general formulas (1a) (1b) or (2a) (2b),
R represents an alkyl chain, and the alkyl chain has 1 to 1 carbon atoms.
A straight-chain alkoxy group having 30 carbon atoms is preferable, but having 6 to 18 carbon atoms is preferable in view of solubility and liquid crystallinity.

General formula (1a) (1b) or (2a)
In (2b), it is possible to introduce a branched alkyl group into R, and a 2-ethyl-hexyl group or the like is suitable. Further, M in the general formulas (1b) and (2b) is a metal atom, and as the metal atom, copper, zinc, lead, cobalt or nickel can be used, and copper or nickel is particularly preferable.

[0012]

The general formula (1a) (2a) or (1) of the present invention
b) The compound represented by (2b) or its metal complex can be produced by the synthetic route shown in FIG. Here, DBU in the figure represents 1,8-diazabicyclo [5,4,0] undec-7-ene, and MX ₂ represents an anhydrous metal halide.

That is, with respect to the general formulas (1a) and (1b), 4,4'-didodecyloxybenzyl ( 7 ) is obtained from 4-methoxybenzaldehyde ( 3 ) which is a starting material.
The synthesis to the chemist Wenz et al.
akromolekulare Chemie RapidCommun.) Volume 6 577
The method described on page [1985] can be used.

Next, 2,3-dicyano-5,6-bis (4-dodecyloxyphenyl) pyrazine ( 8 ) is a chemical journal of chemist Kanakarajan et al. (Journal).
of Organic Chemistry) Vol. 51, p. 5241 [1986
Year] method, and finally the chemist Tomoda (Tomo
da) et al. Chemistry Letter p. 1277 [1
980] or the same method (Chemistry Letter) p. 313 [1983], the target compound octakis (alkoxyphenyl) tetrapyrazinoporphyrazine compound or metal complex can be obtained. Further, the general formulas (2a) and (2b) can also be produced by using exactly the same method as described above, although the starting material (3,4-dimethoxybenzaldehyde ( 9 )) is different.

The compound represented by the general formula (1a) (1b) or (2a) (2b) and the metal complex of the present invention are
It is a blue dye with good solubility. They show high solubility in general-purpose organic solvents such as alkane (aromatic), chlorine, and ether, and are insoluble in lower alcohols and polar solvents such as acetonitrile / dimethylsulfoxide. Purification by chromatography, molecular sieving and solid-liquid extraction methods is possible.

Further, the copper complex and nickel complex of the general formulas (1b) and (2b) exhibit discotic columnar liquid crystallinity. Furthermore, the copper complex and the nickel complex of the general formulas (1b) and (2b) were able to shift the absorption in the Q band to a longer wavelength than the general tetrapyrazinoporphyrazine compound.

[0017]

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited thereto. Example 1 [5, 6, 5 ', 6', 5 ", 6", 5 '", 6'"-
Octakis (4-dodecyloxyphenyl) tetrapyrazino [2,3-b: 2 ', 3'-g: 2 ", 3" -1:
Synthesis of 2 ″ ′, 3 ″ ′-q] porphyrazinato] copper (II) complex (1b-1).

2,3-Dicyano-5,6-bis (4-n
-Synthesis of dodecyloxyphenyl) pyrazine (8-1) .
5.06 g (82.6 mmol) of potassium cyanide and 25.00 g of 4-methoxybenzaldehyde ( 3 )
(184 mmol) in 50 ml of water / 100 ethanol
The mixture was heated under reflux in a ml mixed system to obtain 10.14 g of 4,4′-dimethoxybenzoin ( 4 ) (yield 41%).

18.90 g of crude benzoin ( 4 )
(Ca. 69.4 mmol) and copper sulfate pentahydrate 5
7.20 g (229 mmol), pyridine 110 m
A mixture of 1 and 90 ml of water was heated under reflux to obtain 10.32 g of 4,4′-dimethoxybenzyl ( 5 ) (yield 55
%). Benzyl ( 5 ) 2.62 g (9.69 mmo)
l) and 47% hydrobromic acid aqueous solution 180 ml, acetic acid 12
The 0 ml mixed liquid was heated under reflux to obtain 1.48 g of 4,4′-dihydroxybenzyl ( 6 ) (yield 77%).

Benzyl of 4,4'-dihydroxybenzyl ( 6 ) 1.30 g (5.37 mmol) of N, N-
Anhydrous potassium carbonate 1.7 in dimethylacetamide solution
1 g (12.3 mmol), n-dodecyl bromide 3.0
Add 7 g (12.3 mmol) and heat to reflux 4,4'-
4,4'- which is one of dialkoxybenzyl ( 7 )
1.98 g of didodecyloxybenzyl ( 7-1 ) was obtained (yield 88%).

Under a nitrogen stream, 0.89 g (7.77 mmo) of diaminomaleonitrile was added to 1.90 g (3.11 mmol) of 4,4'-didodecyloxybenzyl ( 7-1 ).
1) and 50 ml of acetic acid were added, and this was heated under reflux for 10 hours. The reaction product was extracted with chloroform, and the organic layer was washed with brine and then dried over anhydrous sodium sulfate.

The solvent was distilled off to obtain a crude product. Purification
Column chromatography (silica gel, benzene: n
-Hexane = 5: 1, Rf value = 0.66), and a pale yellow solid 2,3-dicyano-5,6-bis (4-n-do), which is one of the dicyanopyrazine derivatives ( 8 ). 1.66 g of desyloxyphenyl) pyrazine ( 8-1 )
Got The purification yield was 82%. The product is ¹ H-
NMR (60 MHz) spectrum is JEOL JNM-
The PMX60si high resolution NMR apparatus and infrared absorption spectrum were confirmed to be measured by JASCO A-100 type infrared spectrophotometer.

The result was as follows. Melting point ^{88 ℃ · 1 H-NMR (} CDCl 3, TMS, δ (ppm)) 7.44 (d, 4H, H a, J HH = 7.8), 6.75
(D, 4H, _Hb , _JHH = 8.4), 3.93 (t, 4
_{H, -OCH 2 -, J HH} = 6), 1.25 (m, 46
_{H, - (CH 2) 10} -), 0.87 (m, 6H, -CH
₃ ). IR (KBr, ν (cm ^-1 )) 2940, 2850, 2250, 1600, 1500.

[ 5, 6, 5 ′, 6 ′, 5 ″, 6 ″,
5 ''',6'''-Octakis (4-dodecyloxypheni
Le) tetrapyrazino [2,3-b: 2 ', 3'-g:
2 ", 3", -l: 2 '", 3'" -q] Porphyraji
Synthesis of nato] copper (II) complex (1b-1) .

Under a nitrogen stream, 2,3-dicyano-5,6-
Bis (4-n-dodecyloxyphenyl) pyrazine ( 8-
1 ) 1.20 g (1.84 mmol), 1,8-diazabicyclo [5.4.0] undenka-7-ene (DB
U) 0.42 g (2.8 mmol), anhydrous copper chloride (I
I) 62.0 mg (0.461 mmol) of 1-pentanol solution (15 ml) was heated under reflux for 48 hours. The obtained reaction product was extracted with chloroform, the organic layer was washed with water, and then dried over anhydrous sodium sulfate.

The solvent was distilled off to obtain a blackish brown crude product.
Purification is benzene and tetrahydrofuran (THF)
The desired product, 0.28 g of black-green liquid crystal, was obtained. The purification yield was 23%.

Physical Properties The final refined product is the elemental analyzer 240B manufactured by Perkin Elmer Co., Ltd. for elemental analysis and Hitachi 330 for UV-visible absorption spectrum.
Generation was confirmed using a self-recording spectrophotometer. The phase transition behavior of this compound is FP manufactured by METTLER CORPORATION as a temperature control device.
80 and FP82 equipped with a polarizing microscope (Olympus BH2), using a Rigaku Thermoflex TG-DSC differential scanning calorimeter.

The liquid crystal phase is identified by a temperature controller (Chin).
o model DB1250-BR00) equipped with a self-made hot plate provided with Rigaku Geiger flex, and powder X-ray diffraction measurement by Cu-Kα ray was performed.

The result was as follows.・ Elemental analysis (C ₁₆₈ H ₂₃₂ N ₁₆ O ₈ Cu ₁ molecular weight = 26
67.36) Calculated value (%): C-75.65, H-8.77, N-
8.40 Found (%): C-75.17, H-8.76, N-
8.16 ・ Electron spectrum (λmax (log ε), nm: i
n CHCl ₃ (concentration 1.40 × 10 ⁻⁵ mol / l) 290 (3.79), 322 (3.76), 377
(4.06), 500 (3.53), 662 (3.8
7) The phase transition temperature of this compound is shown in Table 1.

[0030]

[Table 1]

This compound exhibits a discotic tetragonal disordered (Dtet.d) liquid crystal phase at room temperature,
At 111 ° C., it transforms into an unassignable mesophase Dx. When the temperature was further increased, it was confirmed that the compound was a novel discotic liquid crystalline compound, although it decomposed at around 230 ° C.

Further, compared with the derivative (λmax = 634 nm) in which a dodecyl group was directly introduced into the porphyrazine ring, the Q band absorption was 28 nm by having a phenyl group.
Long wavelength shifted.

Example 2 [5, 6, 5 ', 6', 5 ", 6", 5 '", 6'"-
Octakis (4-dodecyloxyphenyl) tetrapyrazino [2,3-b: 2 ', 3'-g: 2 ", 3" -1:
2 "', 3"'-q] porphyrazinato] nickel (I
I) Synthesis of complex (1b-2).

[ 5, 6, 5 ′, 6 ′, 5 ″, 6 ″,
5 ''',6'''-Octakis (4-dodecyloxypheni
Le) tetrapyrazino [2,3-b: 2 ', 3'-g:
2 ", 3" -1: 2 '", 3'" -q] Porphyra zina
G] Synthesis of nickel (II) complex (1b-2) .

2,3-Dicyano-5,6 obtained in Example 1
-Bis (4-n-dodecyloxyphenyl) pyrazine ( 8
-1 ) 1.20 g (1.84 mmol) and DBU
0.42 g (2.8 mmol), anhydrous nickel bromide (I
I) 0.101 g (0.460 mmol) of 1-pentanol solution (15 ml) was heated under reflux for 48 hours. The obtained reaction product was extracted with chloroform, the organic layer was washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off to obtain a dark green crude product. Purification was carried out by reprecipitation from benzene and then tetrahydrofuran (THF) to obtain 0.17 g of a target product, a black-green liquid crystal. The purification yield was 14%.

Physical Properties By the same method as described in Example 1, the production of this compound was confirmed and the liquid crystal phase was identified. Table 1 shows the phase transition of this compound. The compound exhibits a discotic tetragonal disordered (Dtet.d) liquid crystal phase at room temperature and transitions to an unattributable mesophase Dx at 101 ° C. It was confirmed that the compound was a novel discotic liquid crystalline compound, although it decomposed at around 240 ° C. if the temperature was kept raised as it was.

Further, compared with the derivative (λmax = 627 nm) in which a dodecyl group was directly introduced into the porphyrazine ring, the Q band absorption was 26 nm by having a phenyl group.
Long wavelength shifted.

The result was as follows.・ Elemental analysis (C ₁₆₈ H ₂₃₂ N ₁₆ O ₈ Cu ₁ molecular weight = 26
62.52) Calculated value (%): C-75.79, H-8.78, N-
8.42 Found (%): C-75.46, H-8.78, N-
8.23 Electronic spectrum (λmax (log ε), nm: i
n CHCl ₃ (concentration 1.31 × 10 ⁻⁵ mol / l) 296 (3.89), 335 (3.85), 378
(3.96), 434 (3.50), 452 (3.5
9), 602 (3.53), 653 (4.2)

Example 3 [5, 6, 5 ', 6', 5 ", 6", 5 '", 6'"-
Octakis (3,4-didodecyloxyphenyl) tetrapyrazino [2,3-b: 2 ', 3'-g: 2 ", 3"-
1: 2 ''',3'''-q] porphyrazinato] copper (I
I) Synthesis of complex (2b-1).

2,3-dicyano-5,6-bis (3,4
-Didodecyloxyphenyl) pyrazine (14-1)
Success . Potassium cyanide 4.17 g (64.0 mmo
l) and 3,4-dimethoxybenzaldehyde ( 9 ) 2
5.00 g (150 mmol) is heated under reflux with a mixed system of 10 ml of water and 60 ml of ethanol to give 3,3 ′, 4,4 ′.
-Tetramethoxybenzoin ( 10 ) 12.92g was obtained (yield 52%).

Unpurified Benzoin ( 10 ) 17.13
g (ca.51.5 mmol) and copper sulfate pentahydrate 4
2.47 g (170 mmol), pyridine 90 ml,
A mixture of 68 ml of water is heated to reflux for 3, 3 ', 4, 4'
-Tetramethoxybenzyl ( 11 ) 8.17g was obtained (yield 48%). 2.50 g of benzyl ( 11 ) (7.
57 mmol) and 180 ml of 47% hydrobromic acid aqueous solution,
A mixture of 120 ml of acetic acid was heated to reflux to give 3,3 ',
4,4'-tetrahydroxybenzyl ( 12 ) was added to 1.2
1 g was obtained (yield 58%).

[0042] 3,3 ', 4,4' - tetrahydro key benzyl 5.00 g (18.2 mm in Shibenjiru (12)
ol) in N, N-dimethylacetamide solution, 1.71 g (12.3 mmol) of anhydrous potassium carbonate and 22.40 g (80.2 mmol) of n-dodecyl bromide were added, and the mixture was heated under reflux for 3, 3 ', 4, 4'. - it is one of tetra-alkoxybenzyl (13) 3,3 ', 4,4' - to give 14.08g of tetra-dodecyloxy benzyl (13-1) (82% yield).

Under nitrogen stream, 3,3 ', 4,4'-tetradodecyloxybenzyl ( 13-1 ) 4.00 g
(4.22 × 10 ⁻³ mol), 1.14 g (1.06 × 10 ⁻² mol) of diaminomaleonitrile and 100 m of acetic acid.
1 was added, and the mixture was heated under reflux for 12 hours. The reaction product was extracted with chloroform, and the organic layer was washed with water. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated and evaporated to obtain a dark brown solid of the target crude product.

Purification was carried out by column chromatography (silica gel, benzene: chloroform = 1: 1, Rf value =
0.80) and the dicyanopyrazine derivative ( 1
4) it is one of 2,3-dicyano-5,6-bis (3,4-disilazide de siloxy phenyl) pyrazine (14
1 ) 3.67 g of a bright yellow solid was obtained. Purification yield is 8
It was 5%. The product is ¹ H-NMR (60 MHz)
The spectrum was measured by a JEOL JNM-PMX60si high-resolution NMR apparatus, and the infrared absorption spectrum (IR) was measured by a JASCO A-100 type infrared spectrophotometer to confirm generation.

The result was as follows. Melting point 75 ° C. ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)) 7.02 to 6.52 (m, 6H, phenyl), 3.
_{88 (m, 8H, -CH 2} O -), 1.24 (m, 80
_{H, - (CH 2) 10} -), 0.87 (m, 12H, -C
H ₃ ). IR (KBr, ν (cm ^-1 )) 2930, 1600, 1500, 1460, 1430,
1370.

[ 5, 6, 5 ′, 6 ′, 5 ″, 6 ″,
5 ''',6'''-Octakis (3,4-didodecyloxy
Phenyl) tetrapyrazino [2,3-b: 2 ', 3'-
g: 2 ", 3" -1: 2 '", 3'"-q] Porphyra
Synthesis of [dinato] copper (II) complex (2b-1) .

Under a nitrogen stream, 2,3-dicyano-5,6-
Bis (3,4-didodecyloxyphenyl) pyrazine ( 1
4-1 ) 0.25 g (2.45 × 10 ⁻⁴ mol) of 1
Dissolved in 0 ml of 1-pentanol solution, anhydrous copper (II) chloride 8.79 × 10 ⁻³ g (6.13 × 10 ⁻⁵ ml)
And 1,8-diazapicyclo [5,4,0] undec-7
-EN (DBU) 5.59 × 10 ⁻³ g (3.68 × 1)
^0-4 mol) was added and the mixture was heated under reflux for 2 days. The obtained reaction product was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate.

Then, the solvent was distilled off to obtain a dark brown crude product (liquid crystal). Purification was carried out by reprecipitation from ethyl acetate to obtain 4.50 × 10 ^-2 g of the desired product, a black-violet liquid crystal. The purification yield was 18%.

Physical Properties In the same manner as in Example 1, the production of this compound was confirmed and the liquid crystal phase was identified. Table 1 shows the phase transition of this compound. This compound exhibits a discotic hexagonal disordered (Dhd) liquid crystal phase at room temperature.
At 5 ° C., a transition was made to a discotic rectangular disordered Drd (C2 / m) liquid crystal phase. It was confirmed that the compound was a novel discotic columnar liquid crystalline compound, although it decomposed at around 248 ° C. while giving an isotropic liquid when the temperature was further raised.

Further, compared with a derivative (λmax = 634 nm) in which a dodecyl group was directly introduced into the porphyrazine ring, by having a phenyl group, absorption in the Q band was 32 nm.
Long wavelength shifted.

The result was as follows.・ Elemental analysis (C ₂₆₄ H ₄₂₄ N ₁₆ O ₁₆ Cu ₁ molecular weight = 41
41.95) Calculated value (%): C-76.56, H-10.32, N-
5.41 Found (%): C-76.44, H-10.32, N-
5.05 ・ Electron spectrum (λmax (log ε), nm: i
n CHCl ₃ (concentration 1.09 × 10 ⁻⁵ mol / l) 276 (3.83), 347 (3.92), 377
(3.92), 536 (3.54), 602 (3.6
4), 666 (4.33)

Example 4 [5, 6, 5 ', 6', 5 ", 6", 5 '", 6'"-
Octakis (3,4-didodecyloxyphenyl) tetrapyrazino [2,3-b: 2 ', 3'-g: 2 ", 3"-
Synthesis of 1: 2 ′ ″, 3 ′ ″-q] porphyrazinato] nickel (II) complex (2b-2).

[ 5, 6, 5 ′, 6 ′, 5 ″, 6 ″,
5 ''',6'''-Octakis (3,4-didodecyloxy
Phenyl) tetrapyrazino [2,3-b: 2 ', 3'-
g: 2 ", 3" -1: 2 '", 3'"-q] Porphyra
Synthesis of [dinato] nickel (II) complex (2b-2) .

2,3-Dicyano-5,6 obtained in Example 3
-Bis (3,4-didodecyloxyphenyl) pyrazine ( 14-1 ) 1.50 g (1.47 x 10 ^-3 mol)
Was dissolved in 18 ml of 1-pentanol solution, and 8.04 × 10 ⁻² g of anhydrous nickel (II) bromide (3.68) was added to the solution.
X10 ^-4 ml), DBU 0.34 g (2.21 x 10)
^-3 mol) was added and the mixture was heated under reflux for 50 hours. The obtained reaction product was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate. Then, the solvent was distilled off to obtain a dark brown crude product (liquid crystal) of the desired product. Purification
Reprecipitation from ethyl acetate was carried out to give the target compound of 0.
16 g of black-green liquid crystal was obtained. The purification yield was 16%.

Measurement of physical properties By the same method as described in Example 1, the production of this compound was confirmed and the liquid crystal phase was identified. Table 1 shows the phase transition of this compound. This compound exhibits a Dhd liquid crystal phase at room temperature,
At 27 ° C., it was transformed into a Drd (C2 / m) liquid crystal phase. It was confirmed that the compound was a novel discotic columnar liquid crystalline compound, although it decomposed at around 236 ° C. while giving an isotropic liquid when the temperature was further raised.

Compared with the derivative (λmax = 627 nm) in which a dodecyl group was directly introduced into the porphyrazine ring, the Q band absorption was 30 nm by having a phenyl group.
Long wavelength shifted.

The results were as follows.・ Elemental analysis (C ₂₆₄ H ₄₂₄ N ₁₆ O ₁₆ Cu ₁ molecular weight = 41
37.11) Calculated value (%): C-76.65, N-10.33, H-
5.42 Found (%): C-76.51, N-10.30, H-
5.11 ・ Electron spectrum (λmax (log ε), nm: i
n CHCl ₃ (concentration 1.14 × 10 ⁻⁵ mol / l) 314 (3.89), 331 (3.88), 390
(3.83), 514 (3.49), 594 (3.5
3), 657 (4.22)

[0058]

As described above, the octakis (alkoxyphenyl) tetrapyrazinoporphyrazine compound obtained by the present invention is a blue-colored and highly soluble dye having absorption on the longer wavelength side than general tetrapyrazinoporphyrazine compounds. Is. These have high solubility in general-purpose organic solvents and can be purified by recrystallization, column chromatography, molecular sieving and solid-liquid extraction methods, facilitating characterization.

Further, in the monoalkoxy substitution product, discotic tetragonal disordered (Dtet, d)
The liquid crystal phase is, for dialkoxy substitution, discotic hexagonal disordered (Dhd) liquid crystal phase or discotic rectangular disordered (Drd)
(C2 / m)) A discotic columnar liquid crystallinity such as a liquid crystal phase is exhibited.

The compound of the present invention is a compound having a conjugated system wider than usual tetrapyrazinoporphyrazines and can be used in a wet method which makes industrial equipment simple. Therefore, it can be used for display materials, recording materials, photoelectric conversion and the like. There is an excellent effect that can be expected to be developed as a molecular device utilizing functionality.

[Brief description of drawings]

FIG. 1 is a synthetic route diagram of the present invention.

[Explanation of symbols]

1a, 1b General formula of octakis (4-alkoxyphenyl) tetrapyrazinoporphyrazine compound or metal complex 2a, 2b General formula of octakis (3,4-alkoxyphenyl) tetrapyrazinoporphyrazine compound or metal complex 34-methoxy Benzaldehyde 44,4'-dimethoxybenzoin 54,4'-dimethoxybenzyl 64,4'-dihydroxybenzyl 74,4'-dialkoxybenzyl 8 dicyanopyrazine derivative 93,4-dimethoxybenzaldehyde 103,3 '4,4'-Tetramethoxybenzoin 11 3,3 ', 4,4'-Tetramethoxybenzyl 123 3,3', 4,4'-Tetrahydroxybenzyl 13 3,3 ', 4,4'-Tetraalkoxy Benzyl 14 dicyanopyrazine derivative

Claims (4)

[Claims] 1. A tetrapyrazinoporphyrazine compound (1a) or a metal complex (1b) represented by the following general formula (1a) or (1b). [Chemical 1] [Chemical 2] (In the formula, R represents a linear alkyl chain having 1 to 30 carbon atoms or a branched alkyl chain such as a 2-ethyl-hexyl group, and M represents a transition metal ion). 2. A composition capable of adopting a discotic liquid crystal phase, comprising at least one kind of the compound according to claim 1. 3. A tetrapyrazinoporphyrazine compound (2a) or a metal complex (2b) represented by the following general formula (2a) or (2b). [Chemical 3] [Chemical 4] (In the formula, R represents a linear alkyl chain having 1 to 30 carbon atoms or a branched alkyl chain such as a 2-ethyl-hexyl group, and M represents a transition metal ion). 4. A composition capable of having a discotic liquid crystal phase, comprising at least one kind of the compound of claim 3.