TW200305629A - Luminescent compound emitting yellow light, process for producing the same, luminescent element emitting yellow light, and luminescent element emitting white light - Google Patents

Abstract

The objectives of this invention are to provide a luminescent compound emitting yellow light that is a novel single compound capable of emitting yellow light, a process for easily producing the luminescent compound and a luminescent element comprising the single luminescent compound. Another objective of this invention is to provide a luminescent element capable of emitting white light by combining the luminescent compound emitting yellow light with a luminescent compound emitting blue light. The luminescent compound emitting yellow light is represented by the following formula (I): wherein Ar is a specific substituted phenyl or substituted naphthyl, and two Ar's may be the same or different; R1 is hydrogen atom or an alkyl group having 1-5 carbon atoms, and two R1's may be the same or different; and R1a is hydrogen atom or an alkyl group having 1-5 carbon atoms, and two R1a's may be the same or different.

Description

200305629 Screen fiber [Technical Field of the Invention] The present invention relates to a yellow light-emitting compound, a manufacturing method thereof, a yellow light-emitting element, and a white light-emitting element; more specifically, it relates to a novel substance that belongs to a single compound and emits yellow light. Yellow light-emitting compound, which can easily produce such a novel yellow light-emitting compound. By combining a single yellow light-emitting element containing the above-mentioned yellow light-emitting compound with the above-mentioned yellow light-emitting compound and blue light-emitting compound, white light can be emitted white. element. [Prior art] Conventionally, various organic compounds have been proposed in terms of organic electric field light emitting elements (also referred to as "organic motor light emitting elements" or "organic EL elements"). However, organic compounds that emit yellow light, have high luminous luminance, and are stable in both heat and light are currently underdeveloped. The purpose of the present invention is to provide an organic yellow light-emitting compound with high luminous luminance, and / or yellow light emission in the X coordinate of 0.40 to 0.55 and Y coordinate of 0.40 to 0.55 in CIE chromaticity, and stable heat and light, A method for producing the same and a light emitting device that emits yellow or white light using the organic yellow compound. [Summary of the Invention] In order to solve the above-mentioned problem, the yellow light-emitting compound of the present invention is represented by the following formula (1): 312 / Invention Specification (Supplement) / 92-05 / 92104343 7 200305629

(Wherein Ar is a substituent represented by any one of formulae (2), (4), and (5) in Formula (1), the two Ars may be the same or mutually different. R1 means hydrogen Atoms, alkyl groups of 1 to 5 carbons, two R1 may be the same or different from each other. Rla refers to a hydrogen atom, alkyl groups of 1 to 5 carbons, and two & 13 may be the same or mutually Different.) R3 R4

(Among them, R2 refers to a single bond or methylene. R3 refers to a hydrogen atom, a radical having 1 to 5 carbon atoms, a radical oxygen, a residual acid group, or -CFs-O-CF2 formed together with R4.) R4 refers to a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, a carboxylic acid ester group, a fluorine atom, a cyano group, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms, and R3-CF ^ O-CF2 ·, or • CF2-0-CF2- formed together with r5. R5 means a hydrogen atom, an alkyl group having a carbon number of i to 5, an alkoxy group, a carboxylate group, a cyano group, a fluorine atom, A fluorine-containing lower alkyl group having 1 to 5 carbon atoms, and -CF2-0-CF2- formed together with R4, or a group represented by formula (3). When R6 is a hydrogen atom, R 'is a hydrogen atom and a carbon number 1-5 lower fluorine-containing alkyl groups, 1 to 5 carbon alkyl groups, alkoxy groups, or carboxylic acid ester groups; and when R5 is a hydrogen removing atom 312 / Invention Specification (Supplement) / 92-05 / 92104343 8 200305629 is a hydrogen atom. R7 is a hydrogen atom when R6 is a hydrogen atom, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group. Or carboxylate; and when R6 is a group other than a hydrogen atom, it is a hydrogen atom.)

(Wherein R8 refers to a hydrogen atom or -CF2-0-CF2- formed together with R9. R9 refers to a fluorine atom, a cyano group, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms, and a group formed with the above R8 -CF2-0-CF2- or formed together with R1G-CF2-0-CFr. R1C) means a hydrogen atom, a cyano group, a fluorine atom, a fluorine-containing lower alkyl group having a carbon number of i to 5, or the same as R9 -CF2-〇-CF2- co-formed. R11 is a hydrogen atom when R1 () is a hydrogen atom, or a fluorine-containing lower alkyl group having 1 to 5 carbon atoms; and when R1 is a group other than a hydrogen atom, it is a hydrogen atom. )

(Wherein R12 is a fluorine atom, a cyano-containing lower alkyl group having 1 to 5 carbon atoms. K is an integer of 1 to 4, and m is an integer of 1 to 3. R12, which is the total number of m and k, may be Same or different from each other.) 312 / Explanation of invention (Supplement) / 92-05 / 92104343 9 200305629

R 12 rn 〇12 (where R12 is a fluorine atom, a cyano group, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms, k is an integer of 1 to 4, and m is an integer of 1 to 3. The total number of ㈤ and k R may be the same or different from each other.) A preferred aspect of the present invention is a yellow light-emitting compound represented by formula (8).

(Wherein, the formula (8) is the same as that of Rla. R13 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, a carboxylic acid ester group, a fluorine atom, or 1 to 5 carbon atoms. Fluoro-lower alkyl. This R13 may be bonded to a benzene nucleus, and multiple R13 may be the same or different from each other.) Other methods for solving the above problems are the yellow light-emitting compounds shown in (1) above. The production method is characterized by reacting 1,4-dihydroxy-2,5-bis (ethoxyloxycarbonyl) benzene represented by formula (6) with an aromatic amine compound represented by formula (7), The obtained dehydrated product is further dehydrogenated. 312 / Invention Specification (Supplement) / 92-05 / 92104343 10 200305629

II 〇 (wherein R in the formula (6) means that the fluorine atoms R1 may be the same or different from each other.) Alkyl groups having 1 to 5 carbon atoms

Rla A r —NH. · (7) (wherein Ar and RIa in formula (7) are as shown in item 1 of the patent application scope.) Another method for solving the above problems is a yellow light-emitting element, which is characterized by A light-emitting layer containing a yellow light-emitting compound represented by the above formula (1) or formula (8) is provided between a pair of electrodes. Another method for solving the above problems is a white light-emitting element, which is characterized in that a light-emitting layer containing a yellow light-emitting compound and a blue light-emitting compound represented by the above formula (1) or formula (8) is provided between a pair of electrodes.

312 / Description of the Invention (Supplement) / 92-〇5 / 921〇4343 11 200305629 Among them, 'Ar is represented by the formula (1): (Substituents represented by any of formulae (2), (4), and (5)') One Ar may be the same or different. It means a hydrogen atom, an alkyl group having 1 to 5 carbon atoms (preferably a carbon number of 1 to 3 carbon atoms), and two Ri may be the same or different from each other. R is a hydrogen atom and an alkyl group having 1 to 5 carbon atoms (preferably 1 to 3 carbon atoms). The two Rla may be the same or different.

Where 'in the formula (2), R2 means a single bond or a methylene group. R3 means a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, a carboxylic acid ester group, or -CF ^ O-CF2- formed together with r4. R4 means a hydrogen atom, an alkyl group having a carbon number of ^ 5, an alkoxy group, a carboxylic acid ester group, a fluorine atom, a cyano group, and a fluorine-containing lower alkyl group having a number of to 5; and -CF2- 0-CF2 ·, or -CF ^ O-CF2 · formed together with R5. R5 means a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, a carboxylic acid ester group, a cyano group, a fluorine atom, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms, and -CF2 formed together with the above R4 -0_CF2 ... or a group represented by formula (3). R6 is a hydrogen atom when R5 is a hydrogen atom, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, or a carboxylic acid ester group; and when R5 is hydrogen A radical other than an atom is a hydrogen atom. R7 is when R6 is a hydrogen atom, it is a hydrogen atom, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms, an alkyl group having a carbon number, an oxygen group, or a carboxylate group; and when R6 is other than a hydrogen atom When it is a base, it is a hydrogen atom. 312 / Instruction of the Invention (Supplement) / 92-05 / 92104343 12 200305629 When at least one of the above R3 to R7 is an alkyl group having 1 to 5 carbon atoms, the alkyl group may be, for example, methyl, ethyl , Propyl, butyl, and pentyl. A preferred alkyl group is a lower alkyl group having 1 to 3 carbon atoms. When at least one of R3 to R7 is an alkoxy group, examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group. A preferred alkoxy group is a lower alkoxy group having 1 to 3 carbon atoms. When at least one of the R3 to R7 is a carboxylic acid ester group, the carboxylic acid ester group may be, for example, a carboxylic acid methyl group, an ethyl carboxylic acid group, a propyl carboxylic acid group, or a butyl carboxylic acid group. And amyl carboxylate.

R11 wherein R8 is a hydrogen atom or is formed together with R9. R9 means a fluorine atom, a cyano group, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms, -CF2-0-CF2 · formed together with the above-mentioned R8, or -CF 2 · 0 · CF 2-formed together with the R1G . R 1 G means a hydrogen atom, a cyano group, a fluorine atom, a carbon number] to 5 or a fluorine-containing lower alkyl group, or -CF2-0-CF2- formed together with the aforementioned R9. R11 is a hydrogen atom when R1G is a hydrogen atom, or a fluorine-containing lower alkyl group having 1 to 5 carbon atoms; and R1 is a hydrogen atom when it is a group other than a hydrogen atom. The fluorine-containing lower alkyl group having 1 to 5 carbon atoms shown by the above R4, R5, R9, and R1G, in terms of fluorine-containing methyl groups, such as: trifluoromethyl, difluoromethyl, and monofluoromethyl; in fluorine-containing ethyl The basic aspects are: pentafluoroethyl; the fluorine-containing propyl is: 6312 / Explanation of the Invention (Supplement) / 92-05 / 92104343 13 200305629 fluoropropyl; the outer ones are: fluorine-containing pentyl and the like. Among them, a preferred fluorine-containing lower alkyl group is a fluorine-containing methyl group. In the aspect of Ar in the above formula (1), when R2 is a single bond or a methylene group, preferred combinations of R3, R4, R5, and R6 are shown in Table 1. Table 1

Combination example P- R4 Rd R ° 1 1Η 1 cf3 1Η —CF 3 2 1Η 1 F 1 cf3 _ H 3 1Η 1 cf3 1 F 1 H 4 1Η CF 3 1 CN 1 H 5 1Η 1 CN One cf3 -H 6 One Η One F One CN One H 7 One Η One CN One F One H 8 One Η One F One cf3 One H One 9 One CF2 — 〇- -CF2 — One Η One H — 10 One Η One CF 2 — _ -CF 2 — -H 11 one formula (3) -H, -CF3, -CN, one H or -Η 12 one F one F t cf3 one H __ 13 one cf3 one one E CF3 -H In addition to the preferred examples shown in Table 1 above, the preferred examples of Ar can be exemplified by: 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorobenzene Fluorinated phenyl-dioxymethylphenyl 4-trifluoromethylphenyl, such as 3,4-difluorophenyl, and 3,5-difluorophenyl, and 3,5-bis (trifluoromethyl) Trifluoromethylphenyl such as phenyl; and fluorinated trifluoromethylphenyl such as 4-fluoro · 3 · trifluoromethylphenyl and fluorotrifluoromethylphenyl. One of Ar is shown in formula (4)

R m

R 12 k • ⑷ 312 / Invention Specification (Supplement) / 92-05 / 92104343 14 200305629 where 'R12 means a fluorine atom, a cyano group, and a fluorine-containing lower alkyl group having a carbon number of i to 5. k is an integer of 1 to 4, and m is an integer of 1 to 3. The total number of R 1 2 may be the same or different from each other.

One of Ar is represented by the formula (5).

Om where R12 is a fluorine atom, a cyano group, or a fluorine-containing lower alkyl group having 1 to 5 carbon atoms. k is an integer of 1 to 4, and m is an integer of 1 to 3. The total number of R12 of ❿ and] ^ may be the same or different from each other. Since the naphthyl group represented by the formula (4) or the formula (5) has an electron-adsorbing group such as a fluorine atom, a cyano group, a fluorine-containing lower alkyl group having a carbon number of 1 to 5, and the like, yellow light emission is easily generated. The fluorine-containing lower alkyl group having 1 to 5 carbon atoms bonded to the naphthyl group is a fluorine-containing lower alkyl group having 1 to 5 carbon atoms as shown in formula (2). Among the fluorine-containing lower alkyl groups having 1 to 5 carbon atoms bonded to a naphthyl group, a trifluoromethyl group is particularly preferable. In the naphthyl group represented by formula (4), the relevant 1-naphthyl group is as follows: a trifluoromethyl group (trifluoromethyl) bonded at the 2-, 3-, 4-, 5-, 6-, 7-, or 8-position Radical) -1-Zekiyl; fluorine atom is bonded at the 2-, 3-, 4-, 5-, 6-, 7-, or 8-position fluorine-1 · naphthyl group; two trifluoromethyl groups are bonded to 2-digit and 3-digit, 2-digit and 4-digit, 2-digit and 5-digit, 2-digit and 6-digit, 2-digit and 7-digit, 2-digit and 312 / Invention (Supplement) / 92-05 / 92104343 15 200305629 8 Bits, 3 and 4 bits, 3 and 5 bits, 3 and 6 bits, 3 and 7 bits, 3 and 8 bits, 4 and 5 bits, 4 and 6 bits, 4 and 7 bits, 4- and 8-, 5- and 6-, 5- and 7-, 5- and 8-, 6- and 7-, 6- and 8-, or 7- and 8-bis (trifluoromethyl) -1-naphthyl; two fluorine atoms are bonded at the 2 and 3 positions, 2 and 4 positions, 2 and 5 positions, 2 and 6 positions, 2 and 7 positions, 2 and 8 positions, 3 Bits and 4, Bits 3 and 5, Bits 3 and 6, Bits 3 and 7, Bits 3 and 8, Bits 4 and 5, Bits 4 and 6, Bits 4 and 7, Bits 4 and 7 Difluoro-1-naphthalene at 8, 5, and 6, 5 and 7, 5 and 8, 6 and 7, 6 and 8, or 7 and 8 ; Three trifluoromethyl bonds at (2, 3, and 4), (2, 3, and 5), (2, 3, and 6), (2, 3, and 6) 7-digit), (2-digit, 3-digit, and 8-digit), (2-digit, 4-digit, and 5-digit), (2-digit, 4-digit, and 6-digit), (2-digit, 4-digit, and 7-digit), (2 (4, 8 and 8), (2, 5 and 6), (2, 5 and 7), (2, 5 and 8), (2, 6 and 7) Bits), (2 bits, 5 bits, and 8 bits), (3 bits, 4 bits, and 5 bits), (3 bits, 4 bits, and 6 bits), (3 bits, 4 bits, and 7 bits), (3 bits , 4 and 8), (3, 5 and 6), (3, 5 and 7), (3, 5 and 8), (3, 6 and 7) ), (3, 6 and 8), (4, 7 and 8), (4, 5 and 6), (4, 5 and 7), (4, 5 and 8), (4, 6 and 7), (4, 6 and 8), (4, 7 and 8), (5, 6 and 7) , (5, 6 and 8), (5, 7 and 8), and tris (trifluoromethyl) -1 · naphthyl on (6, 7 and 8); Three fluorine atoms are bonded at (2-, 3-, and 4-position), (2-, 3-, and 5-position), (2-, 3-, and 6-position), 312 / Invention Specification (Supplement) / 92 -05/92104343 16 200305629 (2, 3 and 7), (2, 3 and 8), (2), (2, 4 and 6), (2, 4) And 7 digits and 8 digits), (2, 5 and 6 digits), (2, 5 and 5 digits and 8 digits), (2, 6 and 7 digits), (2, 5 (3, 4 and 5 digits), (3, 4 and 6 digits), (3, 4 and 8 digits), (3, 4 and 8 digits), (3, 5 and 6 digits and 7 bits), (3 bits, 5 bits, and 8 bits), (3 bits, 6 bits, 6 bits and 8 bits), (4 bits, 7 bits, and 8 bits), (4 bits, '(4 bits, 5 and 7), (4, 5 and 8), (4), (4, 6 and 8), (4, 7 and 8 and 7), ( 5-, 6-, and 8-positions), (5-, 7-, and (6-, 7-, and 8-positions) trifluoro-1 -naphthyl; and: heptafluoro-1-naphthyl, and the like. In the naphthyl group represented by formula (5), for example, a trifluoromethyl group at the 3-, 4-, 5-, 6-, 7-, or 8-position (a trifluoromethyl fluoride atom is bonded at the 1-position, Fluoro-2-naphthyl at positions 3, 4, 5, and 6; two trifluoromethyl groups are bonded at positions 1 and 3, positions 1 and 5, positions 1 and 6, and positions 1 and 7 Bits, 1 and 4 bits, 3 and 5 bits, 3 and 6 bits, 3 and 8 bits, 4 and 5 bits, 4 and 6 bits, 4 and 7 bits, 5 and 6 bits, 5- and 7-, 5- and 8-, 6-, | and 8-, or 7- and 8-position bis (trifluoromethyl) -2_naphthalene㈢ Sub-bonds at 1-, 3-, and 1-position And 4 digits, 1 and 5 digits, 1 and 7 digits, 1 and 8 digits, 3 and 4 digits, 3 312 / Invention Specification (Supplement) / 92-05 / 92104343, 4 and 5) , (2 digits, 4 and 7 digits), (2 digits and 4 digits), (2 digits and 7 digits), (3 digits, 5 and 7 digits), (35 digits and 6 digits), digits, 6 digits And 7), (5-, 6- and 8-positions), 2,3,4,5,6,7,8- are bonded to 1-, 2-) naphthyl;, 7- or 8-position 1st and 4th and 8th, 37th, 3rd and 4th and 8th, 7th and 6th; two fluorine in situ, 1st and 6th and 5th, 3 17 2003056 29th and 6th, 3rd and 7th, 3rd and 8th, 4th and 5th, 4th and 6th, 4th and 7th, 4th and 8th, 5th and 6th, and 5th With 7-, 5- and 8-, 6- and 7-, 6- and 8-, or 7- and 8-position difluoro-2 -naphthyl; three trifluoromethyl groups are bonded to (1-, 3 and 4), (1, 3 and 5), (1, 3 and 6), (1, 3 and 7), (1, 3 and 8) , (1, 4 and 5), (1, 4 and 6), (1, 4 and 7), (1, 4 and 8), (1, 5 Bits and 6 digits), (1, 5 and 7 digits), (1, .5 and 8 digits), (1, 6 and 7 digits), (1, 5 and 8 digits) , (3, 4 and 5), (3, 4 and 6), (3, 4 and 7), (3, 4 and 8), (3, 5 Bits and 6 digits), (3, 5 and 7 digits), (3, 5 and 8 digits), (3, 6 and 7 digits), (3, 6 and 8 digits), (4, 7 and 8), (4, 5 and 6), (4, 5 and 7), (4, 5 and 8), (4, 6 and 6) With 7 digits), ( (4, 6 and 8), (4, 7 and 8), (5, 6 and 7), (5, 6 and 8), (5, 7 and 8) (Position 8), and tris (trifluoromethyl) -2 · naphthyl on (positions 6, 7, and 8); three fluorine atoms are bonded to (position 1, 3, and 4), (1 (3, 5 and 6), (1, 3 and 6), (1, 3 and 7), (1, 3 and 8), (1, 4 and 5) Bits), (1, 4 and 6 bits), (1, 4 and 7 bits), (1, 4 and 8 bits), (1, 5 and 6 bits), (1 bit , 5 and 7), (1, 5 and 8), (1, 6 and 7), (1, 5 and 8), (3, 4 and 5) ), (3, 4 and 6), (3, 4 and 7), (3, 4 and 8), (3, 5 and 6), (3, 5 and 7 312 / Invention Specification (Supplement) / 92-05 / 92104343 18 200305629), (3, 5 and 8), (3, 6 and 7), (3, 6 Bits and 8 bits), (4 bits, 7 bits and 8 bits), (4 bits, 5 bits and 6 bits), (4 bits, 5 bits and 7 bits), (4 bits , 5 and 8), (4, 6 and 7), (4, 6 and 8), (4, 7 and 8), (5, 6 and 7) ), (5, 6 and 8), (5, 7 and 8), and (6, 7 and 8) trifluoro-2-naphthyl; and 1, 3, 4,5,6,7,8-Heptafluoro-2 · Cai Ji and so on. Moreover, a preferred yellow light-emitting compound can be represented by formula (8).

3 R

3 8 1 R wherein R1 and R] a in formula (8) are as described above. R13 means a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, a carboxylic acid ester group, a fluorine atom, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms (preferably 1 to 3 carbon atoms). This R13 may be bonded to a benzene nucleus in plural, preferably in meta and para positions. The plurality of R 13 bonded to the benzene nucleus may be the same or different from each other. The preferred yellow light-emitting compound can be represented by formula (8 a) m ° ι? 13

312 / Invention Specification (Supplement) / 92-05 / 92104343 200305629 The yellow light-emitting compound of the present invention having the structure represented by formula (1) can be considered as an unshared electron pair (lone pair) electron with a nitrogen atom in the amine group The so-called intramolecular charge movement of the 7Γ electrons moving in the carboxyl group causes resonance stabilization and generates a person who emits dark light. In addition, if an aromatic ring represented by Ar is bonded to a fluorine or a fluorine-containing alkyl group (preferably a fluorine-containing alkyl group), the electron attraction of the carboxyl group to the fluorine or fluorine-containing alkyl group may be considered. The interaction between the attractiveness of the electrons increases the luminous brightness of the yellow luminescent compound. The yellow light-emitting compound represented by Formula (1) can be produced as follows. That is, according to the reaction formula shown in formula (9), 1,4-dihydroxy-2,5-bis (ethoxyloxycarbonyl) benzene shown in formula (6) and the formula shown in formula (7) The aromatic amine compound is reacted, and the dehydration product represented by the formula (8) is synthesized, and then the obtained dehydration product is dehydrogenated to obtain a yellow light-emitting compound represented by the formula (1).

II

HO (6)

ii I (8) 1,4-Diacryl-2,5-di (ethoxyloxy end group) represented by the above formula (6) 312 / Description of the Invention (Supplement) / 92-05 / 92104343 20 200305629 Benzene and the aromatic amine compound represented by the formula (7) can be easily reacted by heating in a solvent. Examples of the solvent include acetic anhydride, acetic acid, acid anhydrides having a carbon number of 5 or less, aromatic solvents such as benzene and toluene, dioxolane, lower alcohols having a carbon number of 1 to 3, and mixed solvents thereof. The reaction temperature is usually 20 to 100 ° C. The reaction time is usually 2 to 24 hours. When the reaction is completed, a dehydration product represented by the formula (8) can be obtained by performing a purification operation and a separation operation in accordance with an ordinary method. The dehydrogenation reaction of the dehydrated product is performed in a solvent such as a polar aromatic solvent such as dichlorobenzene or nitrobenzene. As the dehydrogenating agent, for example, sulfuric acid, p-toluenesulfonic acid and the like can be used. The dehydrogenation reaction is completed by heating to, for example, 50 to 350 ° C, and for example, to 1 to 24 hours. With respect to the produced solution obtained after the dehydrogenation reaction, if a purification operation and a separation operation are performed in accordance with an ordinary method, a yellow light-emitting compound represented by the target formula (1) can be obtained. The yellow light-emitting compound of the present invention is obtained by using 1,4-dihydroxy-2,5-bis (ethoxyloxycarbonyl) benzene represented by formula (6) and an aromatic compound represented by formula (7) The amine compound can be easily manufactured by performing a dehydration reaction and a dehydrogenation reaction. Therefore, the manufacturing method of the yellow light emitting compound is an industrial manufacturing method ^ The yellow light emitting compound of the present invention is used in a light emitting device. This light-emitting element has a structure including an anode, a light-emitting layer containing a yellow light-emitting compound, and a cathode formed on the surface of the light-emitting layer. This light-emitting element is only required to have a light-emitting layer containing the above-mentioned yellow light-emitting compound between the anode and the cathode, and various structures can be adopted. 312 / Invention Specification (Supplement) / 92-05 / 92HM343 21 200305629 The yellow light-emitting element using the yellow light-emitting compound of the present invention will be described with reference to the drawings. Fig. 1 is an explanatory view showing a cross-sectional structure of a yellow light-emitting element having a single-layer organic EL element. As shown in Fig. 1, the yellow light-emitting element A is formed on a substrate 1 on which a transparent electrode 2 has been formed, and a light-emitting material-containing light-emitting layer 3 and an electrode layer 4 are sequentially laminated. This yellow light-emitting element A is a planar light-emitting lighting device if the substrate is flat and is expanded to form a planar shape. If the substrate 1 in FIG. 1 is formed into a cylindrical shape, the entire shape is formed into a tubular shape. In this case, a tubular light-emitting device capable of emitting yellow light like a fluorescent lamp is formed. In addition, the tubular light-emitting lighting device may be a straight tube or a ring such as a fluorescent lamp commonly known as a ring fluorescent lamp. As long as the substrate 1 has a transparent electrode 2 formed on the surface, a known substrate can be used. The substrate 1 may be, for example, a glass substrate, a plastic sheet, a ceramic, a metal plate on which an insulating coating layer is formed on the surface, and the like, which is subjected to insulating processing on the surface. When the substrate 1 is opaque, the yellow light-emitting element is a single-sided lighting device that can illuminate yellow light on the back side of the substrate 1. In addition, when the substrate 1 is transparent, it can be used as a double-sided lighting device that irradiates yellow light from the substrate 1 side of the yellow light-emitting element and its back side. The transparent electrode 2 only needs to have a large work function and is transparent, and has an anode function by applying a voltage, and an electric hole can be implanted into the light-emitting layer 3, and various materials can be used. Specifically, the transparent electrode 2 can be made of ITO, Iri203, Sn02, ZnO, CdO, etc., and inorganic transparent conductive materials of these compounds, and conductive polymer materials such as polyaniline. (Supplements) / 92-05 / 92104343 22 200305629, etc. The transparent electrode 2 is formed on the substrate 1 by a chemical vapor deposition method, a spray pyrolysis method, a vacuum evaporation method, an electron beam evaporation method, a sputtering method, an ion beam sputtering method, and an ion plating method. , Ion assisted distillation (i ο nassist), or other methods can be formed. In addition, when the substrate is formed using an opaque member, the electrode formed on the substrate need not be a transparent electrode. The light-emitting layer 3 is a layer containing the specific yellow light-emitting compound of the present invention. The light-emitting layer 3 is a vapor-deposited film formed by dispersing a specific yellow light-emitting compound of the present invention in a polymer, or by depositing the yellow light-emitting compound on the transparent electrode 2. Examples of the polymer in the polymer film include polyvinyl carbazole, poly (3-endanethiophene), polyfluorene imine containing acrylamide, polymanganese, polyphenylene vinylene, and poly-α-formyl. Styrene, ethylene carbazole / α-methylstyrene copolymer, and the like. Among these, polyvinylcarbazole is preferred. The content of the yellow luminescent compound in the polymer film is usually 0.01 to 2% by weight, and preferably 0.05 to 0.5% by weight. The thickness of the polymer film is usually 30 to 500 nm, and preferably 100 to 300 nm. If the thickness of the polymer film is too thin, the amount of luminous light will be insufficient. If the thickness of the polymer film is too thick, the driving voltage will be too high, so it is best not to use it. In addition, it is not set to be a planar body, a tubular body, a curved body, The flexibility required at the time of a ring body. When the light-emitting layer 3 is a vapor-deposited film, although the thickness of the vapor-deposited film varies depending on the layer structure and the like in the light-emitting layer, it is generally 312 / Invention Specification (Supplement) / 92-05 / 92104343 23 200305629 0 · 1 to 100 nm. When the thickness of the vapor-deposited film is too small, or when it is too large, the above-mentioned problems occur. The electrode layer 4 is made of a material having a small work function, and can be formed using a metal monomer or a metal alloy such as Mg Ag, aluminum alloy, metal calcium, and the like. The preferred electrode layer 4 is an alloy electrode of aluminum and a small amount of lithium. This electrode layer 4 is formed on the surface of the substrate 1 containing the light-emitting layer 3, for example, and can be easily formed by a vapor deposition technique. Regardless of whether the light-emitting layer is formed by a coating method or a vapor deposition method, it is also preferable to interpose a buffer layer between the electrode layer and the light-emitting layer. Examples of the material capable of forming the buffer layer include alkali metal compounds such as lithium fluoride, alkaline earth metal compounds such as magnesium fluoride, oxides such as alumina, and 4,4'-carbazole biphenyl (Cz-TPD). In addition, the material of the buffer layer formed between the anode such as ITO and the organic layer may be, for example: m-MTDATA (4,4,4 " -tris (3-methylphenylphenylamine) triphenylamine ), Phthalocyanine, polyaniline, polythiophene derivatives, inorganic oxides (such as: molybdenum oxide, ruthenium oxide, vanadium oxide), lithium fluoride, etc. These buffer layers can reduce the driving voltage of the organic EL element belonging to the yellow light-emitting element by appropriately selecting the material thereof, can improve the quantum efficiency of light emission, and can achieve the effect of improving the luminous brightness. In this way, the yellow light-emitting element shown in FIG. 1 containing a fluorescent compound capable of emitting yellow light in the light-emitting layer will emit yellow light when a current is applied to the transparent electrode 2 and the electrode layer 4. If the light-emitting system applies an electric field between the transparent electrode 2 and the electrode layer 4, when an electron is implanted from one side of the electrode layer 4, a positive hole is implanted from the transparent electrode 2, and the electrons are recombined in the light-emitting layer 3. In the positive hole, when the energy level 312 / Invention Specification (Supplement) / 92-05 / 92104343 24 200305629 is returned from the conduction band to the valence electron band, energy will be released in the form of light. The yellow light-emitting element A shown in FIG. 1 can be mounted on a wall surface or a ceiling if the overall shape is set to a large-area planar shape, thereby forming a large-area wall-surface yellow light-emitting element or a large-area ceiling yellow light-emitting element. element. That is, the yellow light-emitting element can be used as a surface light source for replacing a point light source such as a conventional fluorescent lamp or an electric light bulb. In particular, the yellow light-emitting element can be used as a surface light source to illuminate or illuminate the wall, ceiling, or floor of a house, office, or vehicle. In addition, the yellow light-emitting element A can also be used for backlights such as a display screen of a computer, a display screen of a mobile phone, and a digital display screen of a money register. In addition, the yellow light-emitting element A can be used as a variety of light sources such as direct lighting and indirect lighting. It can also emit light at night to show recognizable advertising devices, road marking devices, and light-emitting notice boards. Light sources such as brake lights for vehicles. At the same time, since the yellow light-emitting element A has a yellow light-emitting compound containing a specific chemical structure in the light-emitting layer, the light-emitting life is long. Therefore, by using this yellow light-emitting element A, a long-life light source can be formed. Furthermore, a tubular light-emitting body can be formed by laminating the yellow light-emitting element A and a cylindrical substrate 1 and laminating transparent electrodes 2, a light-emitting layer 3, and an electrode layer 4 on the inner surface side of the substrate 1 in this order. Because this yellow light-emitting element A does not use mercury, it can replace the conventional fluorescent lamp using mercury and form a light source with good environmental protection. Next, a second example of the yellow light-emitting element of the present invention is shown. FIG. 2 is a cross-sectional explanatory view of a yellow light-emitting element belonging to 312 / Invention (Supplement) / 92-05 / 92104343 25 200305629 on a multilayer organic EL element. As shown in FIG. 2 ', this yellow light-emitting element b has a transparent electrode 2, a hole transporting layer 5, a light-emitting layer 3a, 3b, an electron transporting layer 6, and an electrode layer 4 layered on the surface of the substrate 1 in this order. The substrate 1, the transparent electrode 2, and the electrode layer 4 are the same as the yellow light-emitting element A shown in FIG. The light-emitting layer of the yellow light-emitting element b shown in FIG. 2 is composed of a light-emitting layer 3a and a light-emitting layer 3b. In the present invention, the light-emitting layer 3a is a vapor-deposited film of a yellow light-emitting compound. The light emitting layer 3b is a layer containing DPVBi which is a main pigment. The hole-transporting substance contained in the hole-transporting layer 5 may be, for example, a triphenylamine-based compound (eg, N, N '· diphenyl-N, N'-bis (m-tolyl) -diphenyl) Aniline (TPD), a-NPD, etc.), actinide compounds, stilbene compounds, complex ring compounds, 7Γ electron star burst positive hole transport materials, etc. The electron-transporting substance contained in the electron-transporting layer 6 is the above-mentioned electron-transporting substance, and examples thereof include 2- (4-fourth butylbenzene) -5- (4-biphenyl) -1,3 2,4-bis (1-naphthyl) -1,3,4-oxadiazole, and 2,5-bis (5, -third-butane) -2 '·; oxazolyl) thiophene and the like. In addition, the electron-transporting substance is preferably a metal complex system material such as aluminum quinolinol complex (Alq3), benzoquinolinol beryllium complex (Bebq2), and the like. The yellow light-emitting element B-based electron transport layer 6 shown in FIG. 2 contains Alq3. The thickness of each layer is the same as that of a multi-layer organic EL device known in the prior art. The yellow light-emitting element B shown in FIG. 2 generates the same function as the yellow light-emitting element shown in FIG. 1 312 / Invention (Supplement) / 92-05 / 92104343 26 200305629 and emits light. Therefore, the yellow light-emitting element B shown in FIG. 2 has the same application as the yellow light-emitting element A shown in FIG. FIG. 3 shows a third example of the yellow light-emitting element of the present invention. Fig. 3 is a cross-sectional explanatory view of a yellow light-emitting element of a multilayer organic EL element. The yellow light-emitting element C shown in FIG. 3 is formed on the surface of the substrate 1, and a transparent electrode 2, a hole transporting layer 5, a light-emitting layer 3, an electron transporting layer 8 and an electrode layer 4 are sequentially laminated. The yellow light-emitting element C shown in FIG. 3 is similar to the yellow light-emitting element B described above. FIG. 4 shows another example of a yellow light-emitting element. The yellow light-emitting element D shown in FIG. 4 has a substrate 1, a transparent electrode 2, a hole transporting layer 5, a light-emitting layer 3, and an electrode layer 4 stacked in this order. In addition to the yellow light-emitting element shown in FIGS. 1 to 4 described above, for example, a hole-transporting substance is laminated between an anode belonging to a transparent electrode formed on a substrate and a cathode belonging to an electrode layer. Hole-transporting layer and an electron-transporting light-emitting layer containing the yellow light-emitting compound of the present invention, and a double-layer organic low-molecular light-emitting element (for example, a hole-transporting layer is laminated between an anode and a cathode). , The yellow light-emitting compound of the present invention as a guest pigment, and a two-layer type pigment-doped light-emitting element containing a light-emitting layer for a main pigment; a layer is laminated between the anode and the cathode A double-layer organic light-emitting element (for example: Between the anode and the cathode, a hole-transporting layer, a secondary pigment, and a layer containing the yellow 312 of the present invention / Invention Specification (Supplement) / 92-05 / 92104343 27 200305629 are laminated. An electron-transporting light-emitting layer, and a double-layer pigment-doped organic light-emitting element); and a hole-transporting layer, a light-emitting layer containing the yellow light-emitting compound of the present invention, and electrons are stacked between the anode and the cathode Transport layer, and constitute a three-layer organic light emitting element. The electron-transporting light-emitting layer of this light-emitting element is usually composed of 50 to 80% of polyvinyl carbazole (PVK), 5 to 40% of an electron-transporting light-emitting agent, and the yellow light-emitting compound of the present invention. 0.01 to 20% by weight can produce white light emission with high luminance. The light-emitting layer preferably contains rubrene as a sensitizer, and particularly preferably rubrene and Alq3. The yellow light-emitting element using the yellow light-emitting compound of the present invention can be used, for example, as a general DC-driven organic EL element, and also as a pulse-driven organic EL element and an AC-driven organic EL element. Furthermore, in the above-mentioned yellow light-emitting element, a white light-emitting element can be formed by replacing the yellow light-emitting compound with the yellow light-emitting compound and the blue light-emitting compound of the present invention. If the light-emitting layer of the light-emitting element of the present invention does not contain the above-mentioned yellow light-emitting compound as a light-emitting substance, the light-emitting layer will emit yellow light. If the light-emitting layer contains a yellow light-emitting compound represented by the formula (1) and a blue light-emitting compound, the light-emitting layer will emit white light. Examples of the blue light-emitting compound include a diphenylvinylbiphenol-based blue light-emitting compound and a stilbene-based blue light-emitting compound. Preferred examples of the diphenylvinylbiphenol-based blue light-emitting compound include D P V B i and the like represented by the general formula (10). 312 / Invention Specification (Supplement) / 92-05 / 92104343 28 200305629

•• (ι〇) When the light-emitting element of the present invention emits white light, the blending ratio between the yellow light-emitting compound and the blue light-emitting compound in the light-emitting layer is usually set to a weight ratio of 5 to 200: 1 0 to 1 00: 5 0 to 20,000, preferably 10 to 100: 50 to 500: 100 to 10,000 ° Light emitting elements that emit yellow light and light emitting elements that emit white light can be used as lighting devices such as fluorescent lamps and display devices Wait. (Example) (Example 1) 1. Dehydration reaction In a 1,000 ml three-neck round bottom flask, 10 g of 4- (trifluoromethyl) aniline and dimethyl-1,4-cyclohexanedi 6.4 g of ketone-2,5-dicarboxylic acid ester, 120 m of ethanol and 120 ml of acetic acid. The contents of this flask were heated to 8 ° C in a silicon bath and stirred at this temperature for 8 hours for reaction. Then, the contents were cooled and filtered with a nutsche, and then the obtained The solid was washed with ethyl acetate and methanol. The washed solid was dried to obtain a yellow powder. The IR and NMR charts of this powder are shown in Figure 5 and Figure 6, respectively. From this IR chart and The NMR chart confirmed that 312 / Invention (Supplement) / 92-05 / 92104343 29 200305629 This yellow powder had a structure represented by formula (11).

2. Dehydrogenation reaction: Put 0.3 g of the yellow powder obtained by the above dehydration reaction into a 500 ml three-necked round bottom flask, and then add 200 ml of 0-dichlorobenzene and 0.02 g of concentrated sulfuric acid. The contents were heated to 150 ° C. with a silicon bath, and the contents were stirred at this temperature for 5 hours to perform a reaction. Then, the contents in the flask were cooled, and the contents were then concentrated using an evaporator. The concentrate was washed with methanol to obtain a yellow solid. Sublimation This yellow solid was refined. The IR and NMR charts of the refined yellow solids are shown in Figures 7 and 8, respectively. From these results, it was confirmed that this yellow solid has a structure represented by the formula (12).

3. Light-emitting element 312 / Invention specification (Supplement) / 92-05 / 92104343 30 200305629 < Light-emitting characteristics 1 > An ITO substrate (50x50mm, manufactured by Sanyo Vacuum Industry Co., Ltd.) was performed in acetone. After 10 minutes of ultrasonic cleaning, 2-propanol was used for 10 minutes of ultrasonic cleaning, and then nitrogen was blown in to dry. After that, the surface of the ITO substrate was cleaned by UV irradiation for 5 minutes using a light surface processor (manufactured by Sun Special Light Source Co., Ltd., with a wavelength of 254 nm). The cleaned ITO substrate was installed in a vacuum evaporation device (made by Daya Vacuum Technology Co., Ltd., UDS-M2-46 type), and a-was laminated under a reduced pressure of 4xl (T6torr or less) The NPD layer was 44 nm, and the layer formed by doping the yellow light-emitting compound (formula (12)) 2.6% into Alq3 was 41 nm. Finally, an aluminum alloy electrode (Al: Li = 99: 1 weight) was vapor-deposited. Ratio, high-purity chemical research institute (product)) thickness of 150 nm, to obtain a yellow light-emitting device with a laminated structure shown in Fig. 1. In addition, the above-mentioned yellow light-emitting compound vapor-deposited layer and the DPVBi layer form the light emission in Fig. 1. Layer 3. Regarding this yellow light-emitting element, the brightness and chromaticity were measured with the gradual increase in voltage of BM-7 Fast manufactured by Debcom (stock). As a result, the brightness was obtained at a voltage of 14 V and a current of 46.4 mA. The result was 73,900 Cd / m2, the chromaticity X was 0.41, and the chromaticity Y was 0.57. ≪ Luminescence characteristic 2> In a 5 ml simple flask, 70 mg of polyvinylcarbazole and 2,5-bis (1-naphthalene) were weighed. 29.7 mg of -1,3,4-oxadiazole (BND) and 0.3 mg of yellow powder represented by the above formula (12), and dichloroethane was added to prepare 5 ml of a luminescent compound solution. This yellow luminescent compound-containing solution was subjected to an ultrasonic cleaner 312 / Invention Manual (Supplementary Note) for 20 minutes by using an ultrasonic cleaner (manufactured by Aisinudi Co., Ltd., US-2). ) / 92-05 / 92104343 31 200305629, and it is sufficiently uniform. The ITO substrate (50 χ 50 mm, ITO transparent electrode thickness 200 μm, Sanrong Vacuum Industry Co., Ltd.) was subjected to ultrasonography for 10 minutes in acetone. After sonic cleaning, 2-propanol was used for 10 minutes of ultrasonic cleaning, and then nitrogen was blown in to dry it. Then, the above-mentioned optical surface processor (wavelength 254nm) was used for 5 minutes of UV irradiation to Using a spin coater (1H-D7, manufactured by Migasa Co., Ltd.), the solution containing the above-mentioned yellow light-emitting compound was dropped on the washed and dried ITO substrate, and the number of revolutions was 1 Spin coating was performed at 500 rpm and a rotation time of 3 seconds to make a film having a dry film thickness of 100 μm. The substrate after film formation was dried in a constant temperature bath at 50 ° C for 30 minutes. , Using a vacuum distillation device (Daya Vacuum Technology Co., Ltd. ( ), VDS-M2-46 type), 4xl (less than T6torr, vapor-deposited alloy with a thickness of about 150 nm (Al: Li = 99: l weight ratio, high-purity chemical research institute (stock)) electrode Thus, a yellow light-emitting element having the structure shown in Fig. 2 was obtained. This yellow light-emitting element was measured for luminance and chromaticity under the condition of slowly increasing the voltage of BM-7 Fast manufactured by Debcom. As a result, under a voltage of 17 V and a current of 20.04 mA, a result of a luminance of 4,266 Cd / m2, a chroma X of 0.41, and a chroma Y of 0.55 was obtained. (Example 2) 1. Dehydration reaction In a 1,000 ml three-neck round bottom flask, 25 g of 3- (trifluoromethyl) aniline and dimethyl-1,4-cyclohexanedione-2 were poured. 16 g of 5-dicarboxylic acid ester, 250 m of ethanol and 250 ml of acetic acid. The contents of this flask were heated to 100 ° C in a silicon bath, and stirred at this temperature for 8 hours to effect a reaction. Then, the contents of 312 / Invention (Supplement) / 92-05 / 92104343 32 200305629 were cooled and filtered with a suction filter, and then the obtained solid was washed with ethyl acetate and methanol. The washed solid was dried to obtain a yellow powder. The IR and NMR charts of this powder are shown in Figure 9 and Figure 10, respectively. From the ir chart and the NMR chart, it was confirmed that the yellow powder had a structure represented by the formula (13).

2. Dehydrogenation reaction 13 g of the yellow powder obtained by the above dehydration reaction was put into a 1,000 ml three-necked round bottom flask, and then 500 ml of o-dichlorobenzene and 0.7 g of concentrated sulfuric acid were added. The contents of this flask were heated to 150 ° C in a silicon bath, and the contents were stirred at this temperature for 5 hours to effect a reaction. Then, the contents in the flask were cooled, and then the contents were concentrated using an evaporator. The concentrate was washed with methanol to obtain a yellow solid. Sublimation refined this yellow solid. The IR and NMR charts of the purified yellow solid are shown in Figure 11 and Figure 12, respectively. From these results, it was confirmed that this yellow solid has a structure represented by Formula (4).

312 / Invention (Supplement) / 92-05 / 92104343 33 ••• ((14) 200305629 3. Light-emitting element < Light-emitting characteristics 1 > In a 5ml simple flask, weigh polyvinylcarbazole 70nig, 2 29.7 mg of 1,5-bis (1-naphthyl) -1,3,4-Πoxazine (BND) and 0.3 mg of yellow powder represented by the above formula (14), and dichloroethane was added to prepare 5 ml of a solution containing a yellow luminescent compound. This yellow luminescent compound-containing solution was sufficiently homogeneous by performing ultrasonic irradiation for 20 minutes using an ultrasonic cleaner (manufactured by Aisinudi Co., Ltd., US-2). The ITO substrate (5 Ox 50mm, I TO transparent electrode thickness 200 μm, manufactured by Sanyo Vacuum Industry Co., Ltd.) was subjected to ultrasonic cleaning in acetone for 10 minutes, and then 2-propanol was used for 10 minutes. After washing, nitrogen was blown in to dry. After that, the light surface processor (wavelength 24 5 nm) was used to perform UV irradiation for 5 minutes to clean it. Using a spin coater (1H-D 7 manufactured by Mikasa Co., Ltd.), the prepared solution containing the yellow light-emitting compound was dropped on the washed and dried ITO substrate, and the number of rotations was 1.5, 5 The spin coating was performed at 00 rpm and a rotation time of 3 seconds to prepare a film having a dry film thickness of 100 μm. The film-formed substrate was dried in a constant temperature bath at 50 ° C for 30 minutes, and then vacuum-deposited using a vacuum evaporation device (Ta Ya Vacuum Technology Co., Ltd., VDS-M2-46 type) at 4xl ( Below T6torr, a 150-nm thick alloy (Al: Li = 99: 1 weight ratio, high-purity chemical laboratory (product)) electrode is vapor-deposited to produce a yellow light-emitting element having a structure shown in FIG. 1. The yellow light-emitting element was measured for brightness and chrominance using a slowly increasing voltage of BM-7 Fast manufactured by Debcom (stock). As a result, the brightness was obtained at 2,188 Cd / m2, chroma X 312 / Invention Specification (Supplement) / 92-05 / 92104343 34 200305629 is 0.42 and chroma γ is 0.46. (Comparative Example 1) Instead of replacing 0.3 mg of yellow powder, change to Except for 0.3 mg of rubrene, the rest were the same as the light-emitting characteristics 2 in Example 1 to make a yellow light-emitting element, and then the light-emitting characteristics were investigated as in Example 1. As a result, the voltage was 20.00 V and the current was 30.35. At mA, the results were obtained with a luminance of i295Cd / m1, a chroma X of 0.43, and a chroma Y of 0.48. (Example 3) 1 · Off Water reaction was carried out in a 1,000 ml three-necked round-bottomed flask. Methyl aminobenzoate 258, monomethyl-1,4-cyclohexanone-2,5-diresidue ester 17.2§, and ethanol 25 were charged. 1111 and 250 ml of acetic acid. The contents of this flask were heated to 115 ° C using a silicon bath. The mixture was stirred at this temperature for 20 hours for reaction. Then, the contents were cooled and filtered with a glass filter. Then, the obtained solid was washed with methanol, ethyl acetate and petroleum ether. The washed solid was dried to obtain a yellow powder. The melting point of this powder was 2 560 ℃, IR chart The NMR chart and the NMR chart are shown in Fig. 13 and Fig. 14, respectively. From this ir chart and NMR chart, it was confirmed that the yellow powder had a structure represented by formula (15).

35 1. Dehydrogenation reaction 312 / Invention specification (Supplement) / 92-05 / 92104343 200305629 Fill 20 g of the yellow powder obtained by the above dehydration reaction into a 10⑽ml three-Q round bottom flask, and then add 500 ml of o-dichlorobenzene and concentrated sulfuric acid 0.9§. The contents of this flask were heated to 160 ° C in a silicon bath, and the contents were stirred at this temperature for 1 hour to react. Then, the contents in the flask were cooled, and the contents were concentrated using an evaporator. The concentrate was washed with methanol and petroleum ether to obtain a yellow solid. This solid has a melting point of 254 ° C. Sublimation refined this yellow solid. The IR and NMR charts of the refined yellow solid are shown in Figure 15 and Figure 16 respectively. From these results, it was confirmed that the yellow solid had a structure represented by the formula (16).

<Light-Emitting Characteristics.> After the ITO substrate (50x50mm, manufactured by Sanyo Vacuum Industry Co., Ltd.) was subjected to ultrasonic cleaning in acetone for 10 minutes, 2-propanol was further used for 10 minutes for ultrasonic cleaning, and then Nitrogen was blown in to dry. After that, UV light irradiation was performed for 5 minutes using a light surface processor (manufactured by Sun Special Light Source (strand), wavelength: 254 nm), and the ITO substrate was cleaned. The cleaned ITO substrate was installed in a vacuum evaporation apparatus (Ta Ya Vacuum Technology Co., Ltd., UDS-M2-46 type), and was laminated under a reduced pressure of 4xl (T6 to 0rr or less). The α-NPD layer is 44 nm, and the yellow 312 shown in the above formula (16) / Invention specification (Supplement) / 92-05 / 92104343 36 200305629 is doped in Alq3 at a proper concentration to form a layer of 20 nm, and then the layer is formed. An Alq3 layer was deposited with a thickness of 20 nm, and an aluminum alloy electrode (Al: Li = 9 9: 1 weight ratio, manufactured by High Purity Chemical Research Institute (stock)) was deposited to a thickness of 150 nm, and the laminate shown in FIG. 1 was obtained. Structured yellow light-emitting element. In addition, the above-mentioned yellow light-emitting compound vapor-deposited layer and DPVBi layer are used to form the light-emitting layer 3 in Fig. 1. In relation to this yellow light-emitting element, the use of BM-7 Fast manufactured by Dekang Corporation has been gradually improved. In the case of voltage, the luminance and chromaticity were measured, and the results are shown in Table 2. (Example 4) 1. Dehydration reaction In a three-necked round-bottomed flask at 1,0000011, 2,6-diisopropyl was poured. 40g of aniline, 23.4g of dimethyl-1,4 · cyclohexanone-2,5-dicarboxylic acid ester, 250m of ethanol and 250ml of acetic acid. The contents were heated in a silicon bath to 115 ° C and stirred at this temperature for 26 hours for reaction. Then, the contents were cooled and filtered through a glass filter, and the obtained solids were then subjected to methanol and ethyl acetate. The ester and petroleum ether are washed. The washed solid is dried to obtain a yellow powder. The melting point of this powder is 23 6 ° C. The IR and NMR charts are shown in Figure 17 and Figure 18 respectively. From this IR chart and NMR chart, it was confirmed that this yellow powder had a structure shown by Formula (17).

Γ 'U

ch3 312 / Invention Manual (Supplement) / 92-05 / 921 (M343 200305629 2. Dehydrogenation reaction) Put 20 g of the yellow powder obtained by the above dehydration reaction into a 1,000 ml three-neck round bottom flask, and then add 5,000 ml of o-dichlorobenzene and 0.9 g of concentrated sulfuric acid. The contents of this flask were heated to 160 ° C using a silicon bath force, and the contents were stirred at this temperature for 1 hour to perform a reaction. Then, the flask was reacted. The contents are cooled, and then the contents are concentrated by an evaporator. The concentrate is washed with methanol and petroleum ether to obtain an orange solid. The melting point of this solid is 245 ° C. This orange is sublimated to refine this orange Solid. The IR and NMR charts of the orange solids obtained are shown in Figures 19 and 20, respectively. From these results, it was confirmed that this orange solid has a structure represented by formula (18). C H3 10ch3 chch3

CH 3 CHCH3 0-GH〇 (18) &lt; Light emitting characteristics &gt; Except replacing the yellow light emitting compound represented by the above formula (16) and changing to the yellow light emitting compound represented by the formula (18), the rest are the same as the above examples. 3 'Investigate luminescence characteristics. The results are shown in Table 2. (Example 5) 1. Dehydration reaction In a 1,000 ml three-necked round-bottomed flask, 2-methoxy-5-methylbenzene 312 / Invention Specification (Supplement) / 92-05 / 92104343 38 200305629 amine 25§, dimethyl-1,4-cyclohexanone-2,5-dicarboxylic acid ester 18.9§, 250 ml of ethanol, and 250 m of acetic acid. The contents of this flask were heated to The reaction was carried out by stirring at 115 ° C for 3 hours at this temperature. Then, the contents were cooled and filtered with a glass filter, and the obtained solid was washed with methanol, ethyl acetate and petroleum ether. The washed solid was dried to obtain a yellow-orange powder. The melting point of this powder is 229 ° C. The IR and NMR charts are shown in Figure 21 and Figure 22, respectively. From the IR chart and the NMR chart, it was confirmed that the yellow powder had a structure represented by the formula (19).

O CH; 3 ch3〇

2. Dehydrogenation reaction 20 g of the yellow-orange powder obtained by the above dehydration reaction was charged into a 1,000 ml three-neck round bottom flask, and then 500 ml of o-dichlorobenzene and 0.9 g of concentrated sulfuric acid were added. The contents of this flask were heated to 160 ° C in a silicon bath, and the contents were stirred at this temperature for 1 hour to react. Then, the contents in the flask were cooled, and then the contents were concentrated using an evaporator. The concentrate was washed with methanol and petroleum ether 'to obtain an orange solid. This solid has a melting point of 201 ° C. Sublimation refined this orange solid 312 / Invention Specification (Supplement) / 92-05 / 92104343 39 200305629 body. The IR and NMR charts of the purified sand-colored solids are shown in Figs. 23 and 24, respectively. From these results, it was confirmed that this orange solid has a structure represented by the formula (20).

CH

och3 3 〇

II CH3〇

Νη

O-GH

C

II 〇 &lt; Light emitting characteristics &gt; Except replacing the yellow light emitting compound represented by the above formula (18) and replacing it with the yellow light emitting compound represented by the formula (20), the rest were the same as in Example 3 above, and the light emitting characteristics were examined. The results are shown in Table 2. (Example 6) 1. Dehydration reaction In a 1,000 ml three-neck round bottom flask, 25 g of 2,5 · dimethylaniline and dimethyl-1,4-cyclohexanone-2,5-di 18.9 g of carboxylic acid ester, 250 m of ethanol and 250 ml of acetic acid. The contents of this flask were heated to 5 ° C using a silicon bath, and stirred at this temperature for 3 hours to perform a reaction. Then, the content was cooled and filtered with a glass filter, and the obtained solid was washed with methanol, ethyl acetate and petroleum ether. The washed solid was dried to obtain a yellow-orange powder. The melting point of this powder is 229 ° C. The IR and NMR charts are shown in Figure 25 and Figure 26, respectively. From this ir diagram 312 / invention specification (supplement) / 92 · 05 / 921〇4343 40 200305629 and NMR diagram, it was confirmed that this yellow powder has a structure represented by formula (21) 3

CH

CH3 〇 /

CH

-ΝΗ

3

G

II Ο (2 1 CH3 2. Dehydrogenation reaction 3

20 g of the yellow-orange powder obtained by the above dehydration reaction was put into a 1,000 ml three-neck round bottom flask, and then 500 ml of o-dichlorobenzene and 0.9 g of concentrated sulfuric acid were added. The contents of this flask were heated to 160 ° C in a silicon bath, and the contents were stirred at this temperature for 1 hour to react. Then, the contents in the flask were cooled, and then the contents were concentrated using an evaporator. The concentrate was washed with methanol and petroleum ether to obtain an orange solid. This solid has a melting point of 255 ° C. Sublimation refines this orange solid. The IR and NMR charts of the purified orange solids are shown in Figures 27 and 28, respectively. From these results, it was confirmed that this orange solid has a structure represented by the formula (2 2). CH

Ο

II CH CH 3 3

-NH 312 / Invention Specification (Supplement) / 92-05 / 92104343 c

C

II 〇 (2 2) 200305629 &lt; Luminescence characteristics &gt; Except replacing the yellow light-emitting compound represented by the above formula (20) and replacing it with the yellow light-emitting compound represented by the formula (22), the rest were the same as in Example 3 above. Luminous properties. The results are shown in Table 2. Table 2 Formula (16) Formula (18) Formula (20) Formula (22) Voltage (V) 18 17 15 13 Current (mA) 14.8 5 1.1 36.6 46.7 Brightness Cd / m '83 700 73 3 00 69600 76500 Color X 0.43 0.46 0.45 0.52 Chroma Y 0.55 0.50 0.46 0.47 Concentration of luminescent compound (%) 2.4 2.0 2.5 2.7 (Industrial applicability) According to the present invention, it is possible to provide a yellow luminescent compound which is a novel substance and has a high luminance and can emit bright yellow light. In addition, a simple manufacturing method capable of industrial manufacturing is also provided, and a yellow light emitting element having a simple structure using the yellow light emitting compound can be provided. [Brief Description of the Drawings] FIG. 1 is a cross-sectional explanatory view showing an example of a light-emitting element of the present invention. Fig. 2 is a cross-sectional explanatory view showing an example of a light-emitting element of the present invention. Fig. 3 is a cross-sectional explanatory view showing an example of a light-emitting element of the present invention. Fig. 4 is a cross-sectional explanatory view showing an example of a light-emitting element of the present invention. FIG. 5 is an IR chart of an intermediate obtained through a dehydration reaction in Example 1. FIG. FIG. 6 is an NMR chart of the intermediate obtained through the dehydration reaction in Example 1. FIG. FIG. 7 is an IR chart of a yellow light-emitting compound obtained by a dehydrogenation reaction in Example 1. FIG. FIG. 8 is 312 / Invention Specification (Supplement) / 92-05 / 92104343 42 200305629 NMR Lu I of the yellow luminescent compound obtained by the dehydrogenation reaction in Example 1. FIG. 9 is the intermediate obtained by the dehydration reaction in Example 2. IR image of the volume. FIG. 10 is an NMR chart of the intermediate obtained by the dehydration reaction in Example 2. FIG. FIG. 11 is an IR chart of a yellow luminescent compound obtained by a dehydrogenation reaction in Example 2. FIG. Fig. 12 is an NMR chart of the yellow luminescent compound obtained by the dehydrogenation reaction in Example 2. FIG. 13 is an IR chart of the yellow powder obtained by the dehydration reaction in Example 3. FIG. 14 is an NMR chart of a yellow powder obtained by a dehydration reaction in Example 3. FIG. Fig. 15 is an IR chart of a yellow luminescent compound obtained by a dehydrogenation reaction in Example 3. FIG. 16 is an NMR chart of a yellow light-emitting compound obtained by the dehydrogenation reaction in Example 3. FIG. FIG. 17 is an IR chart of the yellow powder obtained by the dehydration reaction in Example 4. FIG. FIG. 18 is an NMR chart of the yellow powder obtained by the dehydration reaction in Example 4. FIG. Fig. 19 is an IR chart of a yellow luminescent compound obtained by a dehydrogenation reaction in Example 4. Fig. 20 is an NMR chart of a yellow luminescent compound obtained by a dehydrogenation reaction in Example 4. FIG. 21 is an IR chart of the yellow powder obtained by the dehydration reaction in Example 5. FIG. Figure 22 is the NMR of the yellow powder obtained by the dehydration reaction in Example 5 Figure 0 312 / Explanation of the Invention (Supplement) / 92-05 / 92104343 43 200305629 Figure 2 3 is the yellow obtained by the dehydrogenation reaction in Example 5 IR chart of luminescent compound. Fig. 24 is an NMR chart of a yellow luminescent compound obtained by a dehydrogenation reaction in Example 5.

FIG. 25 is an IR chart of the yellow powder obtained by the dehydration reaction in Example 6. FIG. FIG. 26 is an NMR chart of a yellow powder obtained by a dehydration reaction in Example 6. FIG. Fig. 27 is an IR chart of a yellow luminescent compound obtained by a dehydrogenation reaction in Example 6. Fig. 28 is an NMR chart of the yellow luminescent compound obtained by the dehydrogenation reaction in Example 6. (Description of element symbols) 1 substrate 2 transparent electrode 3 light emitting layer 3 a, 3 b light emitting layer 4 electrode layer 5 hole transporting layer 6 electron transporting layer 8 electron transporting layer A to D yellow light emitting element 312 / invention specification (supplement) / 92-05 / 92104343 44

Claims (1)

200305629 (Wherein Ar is a substituent represented by any one of formulae (2), (4), and (5) in formula (1), two Ar may be the same or different from each other; R1 means a hydrogen atom, C1-C5 alkyl group, two R1 may be the same or different; Rla means a hydrogen atom, C1-C5 alkyl group, two Rla may be the same or different;) R3 R4 (Where 'R2 refers to a single bond or methylene; R3 refers to a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a 7Coxy group, a residual acid group, or -CF ^ O- CF2. R4 means a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, a carboxylic acid ester group, a fluorine atom, a cyano group, a fluorine-containing lower alkyl group having an id of carbon number, and -CF ^ formed together with R3. O-CF2 ... or -CF ^ O-CF2- formed together with R5; R5 means a hydrogen atom, an alkyl group having a carbon number of ^ 5, an alkoxy group, a residual acid ester group, a cyano group, a fluorine atom, and a carbon number. ”Fluorinated lower alkyl group, -CF2-〇-CF2- formed together with R, or a group represented by formula (3); r6 is r5 45 312 / Invention Specification (Supplement) / 92-05 / 92104343 200305629 When it is a hydrogen atom, it is a hydrogen atom, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, or a carboxylic acid ester group, and when R5 is other than a hydrogen atom When R6 is a hydrogen atom, R7 is a hydrogen atom, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, or a carboxyl group. Acid ester group, and when R6 is a group other than a hydrogen atom, it is a hydrogen atom;) R11 (where R8 refers to a hydrogen atom or formed with R9-CF2-0-CF2-; R9 refers to a fluorine atom, a cyano group, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms, and forms together with the above R8 -CF2-0-CF2-, or -CF2-0-CF2 formed together with R1C); R1G means a hydrogen atom, a cyano group, a fluorine atom, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms, or -CF2-0-CF2- formed by the above R9 together; R11 is a hydrogen atom when R1G is a hydrogen atom, or a fluorine-containing lower alkyl group having 1 to 5 carbon atoms, and when R1G is a group other than a hydrogen atom At that time, it was a hydrogen atom;) 312 / Invention (Supplement) / 92-05 / 92104343 46 200305629 (where R12 means a fluorine atom, a cyano group, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms; k means an integer from 1 to 4, m Refers to an integer from 1 to 3; the total number of R12 of m and k can be the same or different; Rlm (where RU is a fluorine atom, a cyano group, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms; k is an integer of 1 to 4; m is an integer of 1 to 3; "^ and k total number R12 can be the same or different). 2. A kind of yellow light-emitting compound, as shown in formula (8) ’ (Wherein R1 and Rla in formula (8) are as described above; R13 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, a carboxylic acid ester group, a fluorine atom, or one having 1 to 5 carbon atoms. Fluorinated lower alkyl; this R1 3 may be bonded to a benzene nucleus, and multiple R13 may be the same or different from each other). 3.—A method for manufacturing a yellow light-emitting compound in the scope of claims 1 or 2 of the patent application, which uses 1,4-dihydroxy-2,5 · bis (ethoxycarbonylcarbonyl312 / invention) represented by formula (6) Instruction (Supplement) / 92-05 / 92104343 47 200305629) benzene, which is reacted with an aromatic amine compound represented by formula (7), and the obtained dehydrated product is dehydrogenated; (Wherein R1 in formula (6) refers to a hydrogen atom, and alkyl groups R1 to C5 may be the same or different from each other;) Rla (7) Ar-NH (wherein formula (7) (Ar and Rla are shown in item 1 of the scope of patent application). 4. A yellow light-emitting element comprising a light-emitting layer containing a yellow light-emitting compound represented by the above formula (1) or (8) between a pair of electrodes. 5 · A white light-emitting element is provided between a pair of electrodes, and a light-emitting layer containing a yellow light-emitting compound represented by the above formula (1) or formula (8) is provided. 312 / Invention Specification (Supplement) / 92-05 / 92104343 48