Specific polycyclic compounds, a material for an organic electroluminescence device comprising said specific polycyclic compound, an organic electroluminescence device comprising said specific polycyclic compound, an electronic equipment comprising said organic electroluminescence device, a process for preparing said polycyclic compounds, and the use of said polycyclic compounds in an organic electroluminescence. (Formula I) (I)

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Provided is a compound of Chemical Formula 1:

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wherein n is 0 or 1, when n is 0, at least one of R1 to R10 is a group of Chemical Formula A, and when n is 1, at least one of R1 to R12 is a group of Chemical Formula A:

##STR00002##

wherein L1 is a direct bond, or a substituted or unsubstituted arylene or heteroarylene group; l1 is an integer of 1 to 5; m is an integer of 1 to 3; when l1 is 2 or greater, the two or more L1s are the same as or different from each other, and an organic light emitting device including the same.

Provided is a compound of Chemical Formula 1:

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wherein n is 0 or 1, when n is 0, at least one of R1 to R10 is a group of Chemical Formula A, and when n is 1, at least one of R1 to R12 is a group of Chemical Formula A:

##STR00002##

wherein L1 is a direct bond, or a substituted or unsubstituted arylene or heteroarylene group; l1 is an integer of 1 to 5; m is an integer of 1 to 3; when l1 is 2 or greater, the two or more L1s are the same as or different from each other, and an organic light emitting device including the same.

A method for producing a purified phthalonitrile is described. The method involves reacting ammonia, oxygen, and xylene in the presence of a catalyst to obtain a product gas containing a phthalonitrile and a cyanobenzamide and then contacting the reaction product gas with an organic solvent to obtain a collection liquid. The collection liquid is distilled by a high boiling point fraction-separating column to obtain a gas that contains the phthalonitrile and the organic solvent from the column top, and to obtain a bottom liquid that contains a cyanobenzamide from the column bottom. The bottom liquid has a phthalonitrile content of 90% by mass or less. The bottom liquid is subjected to combustion, while being kept in a liquid state, and the purified phthalonitrile is obtained by removing the organic solvent from the gas that has been obtained from the column top.

A method for producing a purified phthalonitrile is described. The method involves reacting ammonia, oxygen, and xylene in the presence of a catalyst to obtain a product gas containing a phthalonitrile and a cyanobenzamide and then contacting the reaction product gas with an organic solvent to obtain a collection liquid. The collection liquid is distilled by a high boiling point fraction-separating column to obtain a gas that contains the phthalonitrile and the organic solvent from the column top, and to obtain a bottom liquid that contains a cyanobenzamide from the column bottom. The bottom liquid has a phthalonitrile content of 90% by mass or less. The bottom liquid is subjected to combustion, while being kept in a liquid state, and the purified phthalonitrile is obtained by removing the organic solvent from the gas that has been obtained from the column top.

A compound has, in a molecule, a cyclic structure represented by a formula (1) below; and at least one cyclic structure selected from the group consisting of a cyclic structure represented by a formula (10) below and a cyclic structure represented by a formula (11) below. In the formula (1): R.sub.1 to R.sub.16 are each independently a hydrogen atom, an alkyl group or the like; and R.sub.X and R.sub.Y are each independently an alkyl group.

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The present invention relates to a process for preparation of an electrically doped semiconducting material comprising a [3]-radialene p-dopant or for preparation of an electronic device containing a layer comprising a [3]-radialene p-dopant, the process comprising the steps: (i) loading an evaporation source with the [3]-radialene p-dopant; and (ii) evaporating the [3]-radialene p-dopant at an elevated temperature and at a reduced pressure, wherein the [3]-radialene p-dopant is selected from compounds having a structure according to formula (I) wherein A.sup.1 and A.sup.2 are independently aryl- or heteroaryl-substituted cyanomethylidene groups, the aryl and/or heteroaryl is selected independently in A.sup.1 and A.sup.2 from 4-cyano-2,3,5,6-tetrafluorphenyl,2,3,5,6-tetrafluorpyridine-4-yl, 4-trifluormethyl-2,3,5,6-tetrafluorphenyl, 2,4-bis(trifluormethyl)-3,5,6-trifluorphenyl, 2,5-bis(trifluormethyl)-3,4,6-trifluorphenyl, 2,4,6-tris(trifluormethyl)-1,3-diazine-5-yl, 3,4-dicyano-2,5,6-trifluorphenyl, 2-cyano-3,5,6-trifluorpyridine-4-yl, 2-trifluormethyl-3,5,6-trifluorpyridine-4-yl, 2,5,6-trifluor-1,3-diazine-4-yl and 3-trifluormethyl-4-cyano-2,5,6-trifluophenyl), and at least one aryl or heteroaryl is 2,3,5,6-tetrafluorpirydine-4-yl, 2,4-bis(trifluormethyl)-3,5,6-trifluorphenyl, 2,5-bis(trifluormethyl)-3,4,6-trifluorphenyl, 2,4,6-tris(trifluormethyl)-1,3-diazine-5-yl, 3,4-dicyano-2,5,6-trifluorphenyl, 2-cyano-3,5,6-trifluorpyridine-4-yl, 2-trifluormethyl-3,5,6-trifluorphenyl, provided that the heteroaryl in both A.sup.1 and A.sup.2 cannot be 2,3,5,6-tetrafluorpyridine-4-yl at the same time, respective [3]-radialene compounds, and semiconducting materials and layer, and electronic devices comprising said compounds.

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The present invention relates to a process for preparation of an electrically doped semiconducting material comprising a [3]-radialene p-dopant or for preparation of an electronic device containing a layer comprising a [3]-radialene p-dopant, the process comprising the steps: (i) loading an evaporation source with the [3]-radialene p-dopant; and (ii) evaporating the [3]-radialene p-dopant at an elevated temperature and at a reduced pressure, wherein the [3]-radialene p-dopant is selected from compounds having a structure according to formula (I) wherein A.sup.1 and A.sup.2 are independently aryl- or heteroaryl-substituted cyanomethylidene groups, the aryl and/or heteroaryl is selected independently in A.sup.1 and A.sup.2 from 4-cyano-2,3,5,6-tetrafluorphenyl,2,3,5,6-tetrafluorpyridine-4-yl, 4-trifluormethyl-2,3,5,6-tetrafluorphenyl, 2,4-bis(trifluormethyl)-3,5,6-trifluorphenyl, 2,5-bis(trifluormethyl)-3,4,6-trifluorphenyl, 2,4,6-tris(trifluormethyl)-1,3-diazine-5-yl, 3,4-dicyano-2,5,6-trifluorphenyl, 2-cyano-3,5,6-trifluorpyridine-4-yl, 2-trifluormethyl-3,5,6-trifluorpyridine-4-yl, 2,5,6-trifluor-1,3-diazine-4-yl and 3-trifluormethyl-4-cyano-2,5,6-trifluophenyl), and at least one aryl or heteroaryl is 2,3,5,6-tetrafluorpirydine-4-yl, 2,4-bis(trifluormethyl)-3,5,6-trifluorphenyl, 2,5-bis(trifluormethyl)-3,4,6-trifluorphenyl, 2,4,6-tris(trifluormethyl)-1,3-diazine-5-yl, 3,4-dicyano-2,5,6-trifluorphenyl, 2-cyano-3,5,6-trifluorpyridine-4-yl, 2-trifluormethyl-3,5,6-trifluorphenyl, provided that the heteroaryl in both A.sup.1 and A.sup.2 cannot be 2,3,5,6-tetrafluorpyridine-4-yl at the same time, respective [3]-radialene compounds, and semiconducting materials and layer, and electronic devices comprising said compounds.

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A photoelectric conversion element, including a first electrode, a second electrode, and at least one organic layer being present between the first electrode and the second electrode, in which the organic layer contains at least two kinds of compounds having the same skeletons and different substituents in combination.

The present invention relates to novel light-emitting materials. These materials comprise a non-aromatic spiro polycyclic group. This new side chain could reduce the stacking of the light-emitting materials and result in high PLQY.