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1. (WO2008091088) COMPOSÉ DE CRISTAUX LIQUIDES DISCOTIQUE, COMPOSITION DE CRISTAUX LIQUIDES COMPRENANT UN TEL COMPOSÉ ET FILM OPTIQUE OBTENU AU MOYEN D'UNE TELLE COMPOSITION DE CRISTAUX LIQUIDES
Note: Texte fondé sur des processus automatiques de reconnaissance optique de caractères. Seule la version PDF a une valeur juridique

Description
DISCOTIC LIQUID CRYSTAL COMPOUND, LIQUID
CRYSTAL COMPOSITION COMPRISING THE SAME AND OPTICAL FILM USING THE SAME LIQUID CRYSTAL COMPOSITION
Technical Field
[1] The present invention relates to a discotic liquid crystal compound, a liquid crystal composition comprising the same, and an optical film using the same liquid crystal composition.
Background Art
[2] Recently, as markets on watches, notebook PCs, cellular phones, televisions and monitors have been tremendously extended, the demand for displays of low weight and low power consumption has been greatly increased. A liquid crystal display
(LCD), which is light and thin and requires low power consumption, has been widely applied to such products.
[3] However, an LCD has a disadvantage of viewing angle dependency. In other words, an LCD shows variations in color or light/darkness depending on viewing directions or angles. Also, as a size of such an LCD increase, a viewing angle decreases. As
compared to a conventional CRT (cathode ray tube) device having a viewing angle of about 180° a TFT-LCD with no viewing angle compensation shows a viewing angle of merely about ±50°.
[4] In order to solve the above described problems, various methods have been used, such methods induing a multi-domain method in which pixels are divided in liquid crystal cells to control liquid crystal alignment, a method of controlling voltage, and a method of utilizing an optical compensation film.
[5] The above-mentioned viewing angle dependency of an LCD is caused by the
incident light having a tilt angle to an LCD panel, which shows a birefringence effect different from that of the vertical incident light. In order to compensate for this, a
method of using an optical compensation film has been widely used, in which retardation films having opposite birefringence indexes to a panel are attached onto both surfaces of the panel. Also, as the size of a display panel has increased, a high-quality liquid crystal compensation film has been needed.
[6] A retardation film is obtained by coating an aligned transparent support with liquid crystal, and aligning the liquid crystal along a predetermined direction to the direction of an aligning layer, followed by curing. After aligning, the liquid crystal has a
direction opposite to the direction of liquid crystal cells upon application of voltage, so that light leakage in a black state can be minimized. When such retardation films are combined with a liquid crystal panel so that light is allowed to penetrate through the panel, it is possible to compensate for a light phase difference caused by a difference of light paths because paths of the incident light are similar to each other in all
directions. In addition, it is also possible to perform compensation of a difference in birefringence indexes in upper/lower/left/right directions by optimizing the magnitude of birefringence of each film, an angle formed between films, a rubbing direction and an angle to a polarizer.
[7] Therefore, there is a need for a new liquid crystal compound used for manufacturing a viewing angle compensation film having high-quality characteristics of improving a contrast ratio, and minimizing color variations in a black state depending on viewing angles.
Disclosure of Invention
Technical Problem
[8] Therefore, the present invention has been made in view of the above-mentioned problems, and the present invention provides a new discotic liquid crystal compound used for manufacturing a viewing angle compensation film having characteristics of improving a contrast ratio, and minimizing color variations in a black state depending on viewing angles.
[9] Also, the present invention provides a liquid crystal composition comprising such a compound, and an optical film using the same.
Technical Solution
[10] In accordance with an aspect of the present invention, there is provided a new
discotic liquid crystal compound, a liquid crystal composition comprising the same, an optical film using the same liquid crystal composition, and a liquid crystal display including the optical film.
[11] A new discotic liquid crystal compound according to the present invention is represented by Formula 1 :
[12] [Formula 1]

[14] wherein G represents H,
o
v , or / \ ;
[15] V represents -H, -CH3, -CH2CH3, -F, -Cl, -Br, or -CF3;
[16] X represents -O-, -NH-, C1 ~ C12 alkylene, or a single bond;
[17] A represents C1 ~ C12 alkylene, C2- C12alkenylene, -(CH2CH2O)n-, -(CH2CHCH3O)n-, or -(CHCH3CH2O)n-, and n represents an integer between 1 and 5;
[18] W represents -H, -CH3, -CH2CH3, or -C6H5;
[19] Y represents -O-, -NR-, C1-C18 alkylene, -CH=CH-, -C≡C-, -(CH2)OC(=O)O(CH2)P-,

-(CH2)OOC(=O)(CH2)P-, -(CH2)OC(=O)(CH2)P-, -(CH2)OC(=O)NR(CH2)P-, -(CH2)O
NRC(=O)(CH2)P-, a single bond, -SiH 2-, -SiMe2-, -SiEt2-, -CH2SiH2-, -CH2SiMe2-, -CH

2SiEt2-, -SiH2CH2-, -SiMe2CH2-, or -SiEt2CH2-;
[20] each of o and p independently represents an integer between 0 and 2;
[21] R represents H, C1-C20 alkyl, C2-C20 alkenyl, or C2-C20 alkynyl;



[23] each of Q1 - Q4 independently represents -H, -F, -Cl, -Br, -I, -CN, -OH, -CF3, -CH3, - CH2CH3, -OCH3, -OCH2CH3, or -C(=0)CH3;



[25] Z1 represents C or N; Z2 represents C, N, O, or S;
[26] b represents an integer between 0 and 2; and
[27] c represents an integer between 1 and 6.
Brief Description of the Drawings
[28] The foregoing and other objects, features and advantages of the present invention will become more apparent from the following detailed description when taken in conjunction with the accompanying drawing in which:
[29] FIG. 1 is a photograph taken by a polarizing microscope in a black state when a compensation film manufactured according to Example 3 of the present invention is used. Best Mode for Carrying Out the Invention
[30] A compound represented by Formula 1 of the present invention is a polymerizable liquid crystal compound.

[31] Specifically, in a dscotic liquid crystal compound according to the present invention, a polymerizable group as a substituent is introduced to a disc-shaped core. However, when a polymerizable group is directly attached to a disc-shaped core, it is difficult to maintain an alignment state in polymerization. Therefore, a linking group is introduced between the disc-shaped core and the polymerizable group.
[32] In Formula 1, ring D or ring D-(Y -ring B)c represents a ring-shaped core, G
represents a polymerizable group, and Si-A-X represents a linking group.
[33] The compound represented by Formula 1, which is a discotic liquid crystal
compound, has high stacking ability, and accordingly, can be used for a TN mode
compensation film or O-plate (splay) type compensation film.
[34] Also, in the compound represented by Formula 1, Si is introduced, thereby
improving the processibility of a liquid crystal compound.
[35] The compound represented by Formula 1 of the present invention is easily mixed with various liquid crystal materials, and has high solubility even at low temperatures. Also, the compound represented by Formula 1 is physically and chemically stable and is stable against heat and light, under the application conditions of conventional liquid crystal displays, and forms a liquid crystal mesophase at a preferred range of temperatures. Therefore, the compound represented by Formula 1 may be very useful for forming a liquid crystal composition. In aάϊtion, contrary to a conventional liquid
crystal composition which is deposited as a crystal at room temperature, there is no deposition in a liquid crystal composition comprising the compound represented by
Formula 1 of the present invention, even when the composition is stored at room temperature for longer than a week.
[36] Therefore, the compound represented by Formula 1 is a liquid crystal compound applicable to an optical film which improves a wide viewing angle of various liquid
crystal displays.
[37] In Formula 1, C2-Ci2 alkenylene as A is selected from the group induing - CH=CH-, -CH=CCH3-, -CH2CH=CH-, -CH=CHCH2CH2-, -CH2CH=CHCH2-, -CH2
CH2CH=CH-, -CH=CHCH2CH2CH2-, -CH2CH=CHCH2CH2-, -CH2CH2CH=CHCH2-, and -CH2CH2CH2CH=CH-.
[38] Hereinafter, a method of preparing the compound represented by Formula 1 will be explained, but the scope of the present invention is not limited thereto.
[39] The compound represented by Formula 1 may be prepared by Reaction Scheme 1.
[40] [Reaction Scheme 1]

esterification


[42] Also, the compound represented by Formula 1 may be prepared by Reaction Scheme

2.
[43] [Reaction Scheme 2]

+ < D )— HCOOH l

Formula 5
esterification



[45] In Reaction Schemes 1 and 2, G, X, W, ring B, ring D, b, and c are the same as
defined in Formula 1, and n represents an integer between 1 and 10.
[46] The discotic liquid crystal compound according to the present invention may be
obtained through esterification of the compounds represented by Formulas 2 and 3 in Reaction Scheme 1. Also, the discotic liquid crystal compound according to the
present invention may be obtained through esterification of the compounds represented by Formulas 4 and 5 in Reaction Scheme 2. As a reagent in the esterification,
DCC(dicyclohexylcarbodiimide),
EDC(l-ethyl-3-(3-dimethylamino)propyl)carbodiimide), SOCl 2, COCl2, or
MsCl(mesyl chloride), etc. may be used, and other conventional reagents known in the art also may be used.
[47] Herein, the compound represented by Formula 2 in Reaction Scheme 1 may be
prepared by Reaction Scheme 3, and the compound represented by Formula 4 in
Reaction Scheme 2 may be prepared by Reaction Scheme 4
[48] [Reaction Scheme 3]



[50] [Reaction Scheme 4] Deprotection



[52] In Reaction Schemes 3 and 4, L represents a leaving group, and non-limiting
examples of the leaving group include, but are not limited to, halide, mesylate(-OSO 2 CH3), tosylate(-OSO2C6H5-/>-CH3), etc. Also, each of P1 and P2 independently
represents a protecting group such as THP(tetrahydropyranyl),
TBS(t-butyldimethylsilyl), etc., but other conventional protecting groups known in the art also may be included. G, X, W, ring B, and b are the same as defined in Formula 1, and n represents an integer between 1 and 10.
[53] In lithiation using Ii in Reaction Schemes 3 and 4, instead of Ii, other reagents (for, example BuIi), which are appropriate for the lithiation, may also be used without any particular limitation. Also, in the step of deprotection, conventional reagents known in the art may be used.
[54] Also, silicon derivative, which is added as a reactant in the second steps of Reaction Schemes 3 and 4, may be prepared by Reaction Scheme 5.
[55] [Reaction Scheme 5]


[57] In Reaction Scheme 5, if X is -O-, or -NH-, P is P 1 or P2, and also, if X is C1 ~ C12 alkylene or a single bond, P is L. Herein, P \ P2, and L are the same as defined in
Reaction Schemes 3 and 4
[58] A method for preparing the compound represented by Formula 1 also includes other methods performed via a reaction path similar to Reaction Schemes 1~5.
[59] The present invention provides a liquid crystal composition comprising the
compound represented by Formula 1.
[60] The compound represented by Formula 1 is included in the liquid crystal composition in an amount of 0.1~99.9 wt%, preferably of l~80 wt%, based on the total weight of the composition.
[61] In addition to the above liquid crystal compound represented by Formula 1, the
liquid crystal composition according to the present invention may include other
various compounds, which can be mixed without disturbing liquid crystal properties.

Examples of such compounds include a polymerizable liquid crystal compound, a
polymerizable non-liquid crystal compound, and a polymer, which are currently used in a conventional liquid crystal composition, and may be used at various ratios as
desired. It is preferable that each of the polymerizable compounds has a polymerizable group, such as a vinyl group, a vinyloxy group, an acrylic group, or a methacrylic
group.
[62] The liquid crystal composition according to the present invention may include a
photoreaction initiator as required, and herein, the photoreaction initiator may include conventional initiators known in the art without any particular limitation. Non-limiting examples of the photoreaction initiator include benzoyl ether, benzoyl isobutyl ether, benzoyl isopropyl ether, benzophenone, acetophenone, 4-benzoyl-4'-methyl diphenyl sulfide, benzyl methyl ketal, dimethylamino methyl benzoate,
3,3'-dimethyl-4-methoxybenzophenone, methyl benzoylformate,
2-methyl- 1 -(4-methylthio)phenyl)-2-morpholinopropane- 1 -one,
2-benzyl-2-dimethylamino- 1 -(4-morpholinophenyl)-butane- 1 -one,
1 -hydroxy cyclohexyl phenyl ketone, Irgacure based, etc. Also, the photoreaction
initiator may be added in an amount of 0.001 to 20 parts by weight, preferably 0.01 to
10 parts by weight, based on 100 parts by weight of a polymerizable liquid crystal compound.
[63] Also, the liquid crystal composition according to the present invention may include an organic solvent as required. The inclusion of the organic solvent facilitates the application (coating) of the liquid crystal composition on a substrate such as a film.
[64] Herein, as the organic solvent, conventional organic solvents known in the art may be used without any particular limitation. Non-limiting examples of the organic solvent include: hydrocarbons such as cyclohexane, cyclopentane, benzene, toluene, xylene, butylbenzene, etc.; ketones such as acetone, methyl ethyl ketone, methyl isobutyl
ketone, cyclohexanone, etc.; esters such as ethyl acetate, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, gamma-butyrolactone, etc.; amides such as 2-pyrrolidone, N-methyl-2-pyrrolidone, dimethyl formamide, di- methylacetamide, etc.; halogens such as chloroform, dichloromethane, carbon tetrachloride, dichloroethane, tetrachloroethane, tetrachloroethylene, chlorobenzene, etc.;
alcohols such as t-butyl alcohol, diacetone alcohol, glycerin, monoacetin, ethylene glycol, triethylene glycol, hexylene glycol, ethylene glycol monomethyl ether, etc.;
phenols such as phenol, parachlorophenol, etc.; and ethers such as methoxybenzene, l,2<£methoxybenzene, Methylene glycol dimethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, dethylene glycol dimethyl ether, diethylene glycol diethyl ether, di- propylene glycol dimethyl ether, dipropylene glycol diethyl ether, etc. Also, such an organic solvent can be independently used, or can be used by mixing at least two of these materials, and herein, the usage amount is not limited.
[65] Also, the liquid crystal composition according to the present invention may include a surfactant as required. A surfactant allows a liquid crystal composition to be easily applied on a substrate. As the surfactant, conventional surfactants known in the art may be used without any particular limitation, and the additional amount varies
according to the kind of surfactant, the composition ratio of components of a liquid crystal composition, the kind of solvent, and the kind of substrate.
[66] Also, the liquid crystal composition according to the present invention may include a chiral dopant or a leveling agent that prevents distortion of a spiral structure of liquid crystal or reverse distortion of liquid crystal, etc. as an additional additive.
[67] The liquid crystal composition according to the present invention may be prepared in a conventional manner. Typically, in the preparation, various components are
dissolved at room temperature or high temperature.
[68] The present invention provides an optical film using the liquid crystal composition according to the present invention.
[69] The optical film according to the present invention is manufactured by forming an optically anisotropic layer, that is, a liquid crystal film, on a substrate. Herein, a liquid crystal alignment state in the liquid crystal film can be adjusted by appropriately
selecting a polymerizable liquid crystal compound forming a liquid crystal composition, and other compounds.
[70] Non-limiting examples of the optical film according to the present invention include an A-plate type compensation film, a B-plate type compensation film, a (+)C-plate type compensation film, a (-)C-plate type compensation film, or an O-plate(splay) type compensation film, etc.
[71] In the optical film of the present invention, the substrate may be used without any particular limitation, so long as the liquid crystal film can be formed on its surface.
Examples of such the substrate include a polymer film, a metal, or a glass, etc.
[72] Non-limiting examples of the polymer film include polyimide, polyamide imide, polyamide, polyetherimide, polyetheretherketone, polyetherketone, polyketone sulfide, polyethersulfone, cycloolefin polymer, polysulfone, polyphenylene sulfide, poly- phenylene oxide, polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyacetal, polycarbonate, polyacrylate, acrylic resin, polyvinyl alcohol, polypropylene, cellulose, triacetyl cellulose, epoxy resin, phenol resin, etc., and herein the examples may be a uniaxially oriented film or a biaxially oriented film. Also the polymer film may be used after surface treatment such as hydrophilic treatment or hydrophobic treatment, and may be a laminated film. Also, non-limiting examples of the metal include aluminum, iron, copper, etc., which have slit-shaped surface grooves;
and non-limiting examples of the glass include alkali glass, boric glass, print glass, etc., which have slit-shaped surfaces through etching.
[73] Also, the substrate may have an alignment layer thereon. Non-limiting examples of a material for the alignment layer include polyimide, polyamide, polyacrylate, polyvinyl alcohol, etc.
[74] Some of the substrate materials can be directly used due to sufficient capability of aligning a liquid crystal compound. However, in order to enhance alignment
capability, the substrate materials may be subjected to separate treatment, such as rubbing, stretching, polarization irradiation, or skew ray irradiation, before being used as the substrate.
[75] Herein, the rubbing can be directly performed on a substrate, or can be performed on an alignment layer previously formed on a substrate.
[76] The optical film according to the present invention may be fabricated by common methods well known in the art. As an example, the optical film of the present invention may be fabricated by coating the inventive liquid crystal composition on a substrate, drying the coated liquid crystal composition to thereby aligning the liquid crystal compound, and then curing the aligned liquid crystal compound while maintaining the alignment form of the liquid crystal compound to thereby fix the alignment form.
[77] The coating of a liquid crystal composition on a substrate may be performed in a conventional manner. Non-limiting examples of such a coating include spin coating, roll coating, printing, dipsdrawing coating, curtain coating, die coating, dip coating, etc.
[78] The drying process may be performed in a conventional manner, and herein, a liquid crystal compound is aligned during the drying process or is aligned by additionally heating after the drying process. The conditions of drying vary according to a boiling point of an organic solvent used for a liquid crystal composition, and materials for a substrate and an alignment layer, without any particular limitation. Also, it is possible to dry by heating, or to gradually dry at room or low temperature.
[79] The curing process may be performed by irradiating rays and/or heat-treating on a coated liquid crystal composition. In the process, polymerization is carried out by a polymerizable group of a polymerizable compound, and a liquid crystal compound with a fixed alignment is attached on a substrate, thereby forming a liquid crystal film with an optically anisotropic layer. The wavelengths of the rays used for the curing process may include, but are not limited to, electron beams, ultraviolet rays, visible rays, infrared rays, etc. Also, the heat-treating is generally performed at 10~200°C from 3 seconds to 30 minutes, but the conditions of the heat-treating are not limited to this.
[80] Also, the optical film according to the present invention may be manufactured by coating a liquid crystal composition on a peelable film, drying the composition,
forming a liquid crystal film through a curing process, and transferring the formed liquid crystal film to a substrate by using a gluing agent or adhesives.
[81] The optical film according to the present invention may be used as an optical compensation film or a polarizer using the optical compensation film, and may be provided in a liquid crystal display.
[82] Reference will now be made in detail to the preferred embodiments of the present invention. However, the following examples are illustrative only, and the scope of the present invention is not limited thereto.
[83] [Example 1]



[85] 1.0 equivalent of a compound 7 was dissolved in a dry THF solvent and a CH2Cl2 solvent, and 1 equivalent of MsCl and 1.1 equivalents of N,N-diisopropylethyl amine were added at O0C, and then, acid chloride was prepared through stirring for 30
minutes. Next, 1.1 equivalents of JV,./V-diisopropylethylamine, 0.3 equivalents of
DMAP, and 0.1 equivalents of 2,3,6,7, 10,11-hexahydroxytriphenylene were added to acid chloride at O0C. Then, after stirring at room temperature under a nitrogen atmosphere for about 20 hours, the mixture was worked up with water and ether and separated via silica gel column chromatography to obtain a compound 8 at a yield of about 80%. 1HNMR (400MHz, CDCl3): δ 0.29 (s, 36H), 0.66-0.78 (m, 12H),
1.55-1.78 (m, 12H), 1.80-1.93 (m, 12H), 413 (t, 12H), 5.82 (d, 6H), 6.12 (dύ, 6H),
6.40 (d, 6H), 7.15 (d, 12H), 7.89 (d, 12H), 8.37 (s, 6H).
[86] [Example 2]



[88] 1.0 equivalent of a compound 9 was dissolved in a dry THF solvent and a CH2Cl2 solvent, and 1 equivalent of MsCl and 1.1 equivalents of JV,./V-diisopropylethyl amine were added at O0C, and then, acid chloride was prepared through stirring for 30
minutes. Next, 1.1 equivalents of JV,./V-diisopropylethylamine, 0.3 equivalents of
DMAP, and 0.1 equivalents of 2,3,6,7, 10,1 l-hexahjdroxytriphenylene were added to acid chloride at O0C. Then, after stirring at room temperature under a nitrogen atmosphere for about 20 hours, the mixture was worked up with water and ether and separated via silica gel column chromatography to obtain a compound 10 at a yield of about 82%. 1HNMR (400MHz, CDCl3): δ 0.30 (s, 36H), 0.67-0.80 (m, 12H),
1.59-1.83 (m, 12H), 414 (t, 12H), 5.83 (d, 6H), 6.12 (dd, 6H), 6.41 (d, 6H), 7.15 (d,
12H), 7.89 (4 12H), 8.43 (s, 6H).
[89] [Example 3: Manufacture of a liquid crystal composition and a compensation film] [90] First, 9.28g of the liquid crystal compound 8 according to Example 1 was dissolved in 30g of methyl ethyl ketone. Next, 600mg of Irgacure 907
(2-Methyl-4'-(methylthio)-2-morpholinophenone), 40mg of FC-4430 as alignment promoter, and 80mg of BYK-300 as leveler were added thereto, and the reaction
mixture was sufficiently shaken. After complete dissolution, particles were removed using a particle filter, thereby preparing coating liquid (a liquid crystal composition).
Then, a rubbing process was performed on a glass with a PVA alignment layer, and the prepared coating liquid was spin-coated on the glass at 2000 rpm for 20 seconds. The coated product was dried in an oven at 15O0C for 1 minute, and UV rays
(200W~80W/m) were irradiated thereto to provide a compensation film.
[91] [Example 4: Manufacture of a liquid crystal composition and a compensation film]

[92] A compensation film was manufactured in the same manner as described in Example

3, except that the liquid crystal compound 10 according to Example 2 was used instead of the liquid crystal compound 8 according to Example 1.
[93] [Comparative Example 1: Manufacture of a liquid crystal composition and a compensation film]
[94] A compensation film was manufactured in the same manner as described in Example

3, except that a conventional discotic liquid crystal compound
(2,3,6,7,10,1 l-Hexakis(4-(4-acryloxybutane-l-oxy)benzenecarbonyloxy)triphenylene) (Fuji) was used instead of the liquid crystal compound 8 according to Example 1.
[95] [Determination of physical properties of a compensation films]
[96] For each of the compensation films according to Examples 3 and 4, its thickness, refractive index, retardation, and viewing angle, etc. were measured.
[97] Specifically, the thickness was measured by using a micro-gauge, and the birefringence index was measured at a center wavelength of 550nm by using an Abbe re- fractometer. Also, the value of wavelength dispersion with a ratio of 450nm/650nm was obtained by measuring UV dispersion by an Axo scan apparatus, and the viewing angles in upper/lower/left/right directions were measured by attaching each of the
compensation films to a TN liquid crystal display. The results are shown in Table 1.
[98] Table 1
[Table 1]
[Table ]


[99] As can be seen from Table 1, the compensation films obtained by using the dscotic liquid crystal compound according to the present invention have wider viewing angles than a conventional film.
[100] FIG. 1 is a photograph taken by a polarizing microscope in a black state when a compensation film according to Example 3 is used.
[101] In general, a compensation film is used to prevent light leakage in a black state.
Since the degree of black color in the black state is important in contrast and a viewing angle, it can be said that the purer the black color, the better the compensation film.
Therefore, with reference to the pure black state photograph taken by a polarizing microscope shown in FIG. 1, the surface quality and the alignment state of the film
according to Example 3 are determined, and accordingly, it is determined that the film has an excellent alignment state, and thus is suitable for an optical compensation film. Industrial Applicability
[102] As can be seen from the foregoing, a high-quality viewing angle compensation film, which improves a contrast ratio measured at a tilt angle when compared to a contrast ratio measured from the front surface, and minimizes color variations in a black state depending on viewing angles, can be fabricated by using the liquid crystal composition comprising the discotic liquid crystal compound according to the present invention.
[103] Although several exemplary embodiments of the present invention have been
described for illustrative purposes, those skilled in the art will appreciate that various modifications, aάϊtions and substitutions are possible, without departing from the
scope and spirit of the invention as disclosed in the accompanying claims.