TWI238816B - 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 (1), 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

1238816 Meiling [Technical field to which the invention belongs] The present invention relates to a yellow light-emitting compound, a method for manufacturing the same, a yellow light-emitting element, and a white light-emitting element; more specifically, it relates to a yellow color of a novel substance that is a single compound and emits yellow light A light-emitting compound that can easily produce such a novel yellow light-emitting compound. A white light-emitting element that can emit white light by combining a single yellow light-emitting element containing the above-mentioned page-color light-emitting compound with the above-mentioned yellow and blue light-emitting compounds . [Prior art] Conventionally, various organic compounds have been proposed in terms of organic electric field light emitting devices (also referred to as "organic motor light emitting devices" or "organic EL devices"). However, organic compounds that can emit yellow light, have high luminous brightness, and are stable in both heat and light are currently underdeveloped. The purpose of the present invention is to provide an organic yellow with a high luminous luminance and / or a yellow luminescence of X coordinate of 0.4 × 0.55 and Y coordinate of 0.40˜0.55 in CIE chromaticity and stable heat and light. Light-emitting compound, method for producing the same, and light-emitting element 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 / Description of the Invention (Supplement) / 92-05 / 92104343 7 1238816

R

Γ A R I ο

R——N a 1

a 1X R (wherein Ar is a substituent represented by any one of formulas (2), (4), and (5) in formula (1), two Ar may be the same or different from each other. R1 is Refers to a hydrogen atom and an alkyl group having 1 to 5 carbon atoms. Two R1 can be the same or different. Rla refers to a hydrogen atom and an alkyl group having 1 to 5 carbon atoms. The two Rla can be the same or mutually different. Different.) R3 R4 \ __ / /,-, Λ ——R2— ((J / -R5 —— (2) \ vy / (where R2 means a single bond or a methylene group. R3 means a hydrogen atom, Alkyl, alkoxy, carboxylate, or -CF2-0-CF2- formed together with r4. R4 means a hydrogen atom, an alkyl or alkoxy group having 1 to 5 carbons. , Carboxylic acid ester group, fluorine atom, cyano group, fluorinated lower alkyl group with 5 to 5 carbon atoms, -CF2-O-CF2- formed with R3, or -CF ^ O-CF2- formed with R5 R5 means a hydrogen atom, an alkyl group having a carbon number of U, an alkoxy group, a carboxylate group, a cyano group, a fluorine atom, a carbon number of 5 to 5 and a -CF2- formed with R4 together. -CF2-, or a group represented by formula (3). When r5 is a hydrogen atom, '帛 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 alkyl group. Oxygen or carboxylic acid ester group; when it is a group other than hydrogen atom 8 312 / Invention Specification (Supplement) / 92-05 / 92104343 1238816, it is a hydrogen atom. R7 is when R6 is hydrogen: it is hydrogen Atom, fluorine-containing lower alkyl group having i to 5 carbon atoms, alkoxy group having 1 to 5 carbon atoms, or carboxylic acid ester group; and when R 6 is a group other than a hydrogen atom, it is a hydrogen atom.) 7-, it is Alkyl, when ...

(Wherein 'R8 means hydrogen atom or _CF2 formed together with r9 and R9 means fluorine atom, cyano group, and fluorine-containing lower alkyl group R8 having a carbon number of 1 to 5 -CF2-0-CF2-, or CF2- formed with R1 (). R1 () means hydrogen atom, cyano group, fluorine atom, carbon number

Lower alkyl, or -CF2-0-CF2- formed together with R9. When R1Q is a hydrogen atom, it is a hydrogen atom, or a shou group containing 1 to 5 carbon atoms; and when R1G is a group other than a hydrogen atom, it is hydrogen J 0-CF 2-0 and -CF Fluorine-containing RI] 2 ~ 〇 ~ is a good, low-level hospital I. )

(Among them, R12 means fluorine atom, cyano group, fluorine-containing low k with 1 to 5 carbon number means 1 to 4 integer, and m means 1 to 3 integer. The total number of m and k may be the same or mutual. Different.) 312 / Invention Specification (Supplement) / 92-05 / 92104343 Grade Alkyl. Number of R12 1238816

(Among them, R12 means fluorinated fluorene, cyano, and 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. R12, which is the total number of m and k, may be They are 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, r1 and Rla in formula (8) are as described above. R1 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 R 13 may be bonded to a benzene nucleus, and multiple R 13 may be the same or different from each other.) For other methods to solve the above problems, the yellow light emission shown in (1) above The method for producing a compound is characterized in that the 1,4-dihydroxy-2,5-bis (ethoxyloxycarbonyl) benzene represented by the formula (6) is reacted with the aromatic amine compound represented by the formula (7). The reaction is followed by dehydrogenation of the obtained dehydrated product. 312 / Invention Specification (Supplement) / 92-05 / 92104343 10 1238816

(Wherein R1 in formula (6) means a fluorine atom and a carbon number of 1 and R1 may be the same or different from each other.)

Rla

I • ⑺

Ar-NH (wherein Ar and in formula (7) are as shown in item i of the patent application scope.) Another method for solving the above-mentioned problem is a yellow light-emitting element, which is characterized by being provided between a pair of electrodes. A light-emitting layer of a yellow light-emitting compound represented by the above formula (1) or formula (8). 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 represented by the above formula (1) or formula (8) and a blue light-emitting compound is provided between a pair of electrodes. Naiwu Chemical Light Hair Color 1 Yellow Form Fang Ming Shifa Display

R

Γ A I N R 1 ο

R

a 1X 312 / Invention Specification (Supplement) / 92-05 / 921 (M343

II 1238816 wherein the two Ars represented by the "Ar system of formulae (2), (4) and (5)" may be the same or different from each other. Ri means a hydrogen atom and an alkyl group having 1 to 5 carbon atoms (preferably 1 to 3 carbon atoms). The two may be the same or different from each other. Rla means a hydrogen atom, a carbon number of 1 to 5 (preferably a carbon number alkyl group, and two R1 3 may be the same or different from each other).

However, in 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 -CFs-O-CF2- formed together with R4. R4 refers to 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 carbon atoms, which are formed together with the above-mentioned R3-CF2- 0-CF2 ·, or -CF ^ O-CF2 · formed together with R5. R5 is a hydrogen atom, a radical having a carbon number of 1 to 5, a radical oxygen, a carboxylic acid ester group, a cyano group, a fluorine atom, a fluorine-containing lower alkyl group having a carbon number of 1 to 5, and formed together with the above-mentioned R4-CF2 -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 When it is a group other than an atom, it is a hydrogen atom. When R6 is a hydrogen atom, R7 is a hydrogen atom, a fluorinated 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 R6 is hydrogen When it is a group other than an atom, it is a hydrogen atom. 312 / Instruction of the Invention (Supplement) / 92-05 / 92104343 12 1238816 When at least one of the above R3 to R7 is an alkane having 1 to 5 carbon atoms, the alkyl group may be, for example, methyl, ethyl, propyl , Butyl and preferred alkyl are lower alkyl having 1 to 3 carbon atoms. When one of R3 ~ I is an alkoxy group, the alkoxy group may be ethoxy group, propoxy group, butoxy group, pentoxy group, or the like. A lower alkoxy group having 1 to 3 alkane groups is preferred. When at least one of the above R3 to R7 is an acid ester group, the carboxylic acid ester group may be, for example, a methyl carboxylate group, a propyl carboxylate group, a butyl carboxylate group, and an amyl carboxylate group. : In the case of pentyl etc. (7 in which at least methoxy and oxy are carbon and one is cumyl, carboxylic acid, etc.

Among them, R8 refers to a hydrogen atom or -CF2- formed together with R9-R2 refers to a fluorine atom, a cyano group, and a fluorine-containing lower alkyl group R8 having a carbon number of 1-5-CF2-0-CF2-, or -CF2-O-CF2- formed together with R1G. R1G means a hydrogen atom, a cyano group, a fluorine atom, a fluorine-containing lower alkyl group of stone, or -c F 2-c formed with R 9 above, and R 11 is a hydrogen atom when R 1C) is a gas atom, or The carbon number is 1 to lower alkyl; when R1 is a group other than a hydrogen atom, the R4, R5, R9 and R1G shown above have a low carbon content of 1 to 5 in terms of fluorine-containing methyl groups such as trifluoromethyl, difluoromethyl, and monofluoro-based groups such as pentafluoro Ethyl; 312 / Invention Specification (Supplement) / 92-05 / 92104343 0-CF 2-with respect to fluoropropyl. , With the above denominations 1 to 5 丨 -CF2-. The fluorine-containing g of 5 is a hydrogen-based radical, fluoromethyl; for example: six 13 1238816 fluoropropyl; for example, 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 R0 R4 R " R ° 1 1Η -cf3 -H 1 CF 3 2 1Η -F —CF 3 -H 3 -Η —cf3 -F -H 4 1Η —cf3 -CN -H 5 -Η- CN -cf3 -H 6 -Η -F -CN -H 7 -Η -CN -F -H 8 -Η -F -CF 3 -H 9 -CF 2 — 〇— CF 2 ——H —H 10 -H —CF 2 — 〇—CF 2 ——H 11 -H Formula (3) -h, -cf3, -cn, or -H—H 12 -F -F—CF 3—H 13—cf3—H -cf3 — H In addition to the preferred examples shown in Table 1 above, preferred A1 · examples include, for example: 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorobenzene Groups, fluorinated phenyl groups such as 3,4-difluorophenyl, and 3,5-difluorophenyl; 3-trifluoromethylphenyl, trifluoromethylphenyl, and 3,5-bis (tri Trifluoromethylphenyl such as fluoromethyl) phenyl; and fluorinated trifluoromethylphenyl such as 4-fluoro-3-trifluoromethylphenyl and 6-fluoro-2-trifluoromethylphenyl Wait.

One of Ar is shown in formula (4).

312 / Description of the Invention (Supplement) / 92-05 / 92104343 14 1238816 Among them, R12 means a fluorine atom, a cyano group, and a fluorine-containing lower alkyl group having 1 to 5 carbon atoms. k is an integer of 1 to 4, and π is an integer of 1 to 3. The total number of R12 of m and k may be the same or different from each other.

One of Af is shown in formula (5).

m Here, R12 means a fluorine atom, a cyano group, and 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 may be the same as 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 low-carbon group containing 1 to 5 carbon atoms, etc., 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 fluorine-containing lower alkyl groups having 1 to 5 carbon atoms bonded to naphthyl group, trifluoromethyl group is particularly preferred. In the naphthyl group represented by formula (4), the related 1-naphthyl group is as follows: a trifluoromethyl group (trifluoromethyl) bonded at the 2-, 3-, 4-, 5-, 6-, 7-, or 8-position Radical) -1 · naphthyl; _atom is fluoro-1 -naphthyl bonded at the 2-, 3-, 4-, 5-, 6-, 7- or 8-position; two trifluoromethyl groups are bonded to 2 and 3 digits, 2 and 4 digits, 2 and 5 digits, 2 and 6 digits, 2 and 7 digits, 2 and 312 / Invention Manual (Supplement) / 92-05 / 92104343 15 1238816 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-bit 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 8-, 5- and 6-, 5- and 7-, 5- and 8-, 6- and 7-, 6- and 8-, or 7- and 8-position difluoro naphthalene ; Three trifluoromethyl bonds at (2, 3, and 4), (2, 3, and 5), (2, 3, and 6), (2, 3, and 6) 7 digits, 2 digits, 3 digits, and 8 digits, 2 digits, 4 digits, and 5 digits, 2 digits, 4 digits, and 6 digits, 2 digits, 4 digits, and 7 digits, 2 digits (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); Each fluorine atom is bonded to (2-, 3-, and 4-position), (2-, 3-, and 5-position), (2-, 3-, and 6-position), 312 / Invention Specification (Supplement) / 92- 05/92104343 16 1238816 (2, 3, and 7), (2, 3, and 8), (2, 4 and 5), (2, 4 and 6), ( (2, 4 and 7), (2, 4 and 8), (2, 5 and 6), (2, 5 and 7), (2, 5 and 7) 8 bits), (2 bits, 6 bits, 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, 7 and 7), (3, 4 and 8), (3, 5 and 6), (3, 5 and 7), (3, 5 and 8) Bits), (3 bits, 6 bits, and 7 bits), (3 bits, 6 bits, and 8 bits), (4 bits, 7 bits, and 8 bits), (4 bits, 5 bits, and 6 bits), (4 bits , 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 (6, 7 and 8) On-trifluoro-l) - naphthalenyl; and 2,3,4,5,6,7 58-- heptafluoro / 1-naphthyl and the like. In the naphthyl group represented by formula (5), for example, a (trifluoromethyl) group in which a trifluoromethyl group is bonded at the 1, 3, 4, 5, 6, 7, or 8 positions 2 · naphthyl; fluoro-2-naphthyl with atoms bonded at 1, 3, 4, 5, 6, 7, or 8 positions; two trifluoromethyl groups bonded at 1 and 3 Bits, 1 and 4 bits, 1 and 5 bits, 1 and 6 bits, 1 and 7 bits, 1 and 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 bits, 5 and 6 bits, 5 and 7 bits, and 5 bits Bis (trifluoromethyl) -2-naphthyl with 8-, 6- and 7-, 6- and 8-, or 7- and 8-position; two fluorine atoms are bonded at 1-, 3-, and 1 Bit 4 and Bit 1, Bit 5 and Bit 1, Bit 6 and Bit 1, Bit 7 and Bit 1, Bit 8 and Bit 3, Bit 4, Bit 3 and Bit 5, 3 312 / Invention Specification (Supplement) / 92-05 / 92104343 17 1238816 bits and 6 bits, 3 bits and 7 bits, 3 bits and 8 bits, 4 bits and 5 bits, 4 bits and 6 bits, 4 bits and 7 bits, 4 bits and 8 bits, 5 bits Difluoro-2 -naphthyl in positions 6 and 5, 5 and 8, 6 and 7, 6 and 8, or 7 and 8; three Fluoromethyl is bonded at (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 digits), (1, 5 and 6 digits), (1, 5 and 7 digits), (1, 5 and 8 digits), (1, 6 and 7 digits), ( 1-digit, 5-digit and 8-digit), (3-digit, 4-digit and 5-digit), (3-digit, 4-digit and 6-digit), (3-digit, 4-digit and 7-digit), (3-digit, 4-digit and 8 bits), (3 bits, 5 bits, and 6 bits), (3 bits, 5 bits, and 7 bits), (3 bits, 5 bits, and 8 bits), (3 bits, 6 bits, and 7 bits), (3 bits (6, 8 and 8), (4, 7 and 8), (4, 5 and 6), (4, 5 and 7), (4, 5 and 8) Bits), (4 bits, 6 bits, and 7 bits), (4 bits, 6 bits, and 8 bits), (4 bits, 7 bits, and 8 bits), (5 bits, 6 bits, and 7 bits), (5 bits , 6 and 8), (5, 7 and 8), and tris (trifluoromethyl) -2-naphthyl on (6, 7 and 8); three fluorogens 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 and 6), (1, 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 digits, 5 digits, and 6 digits), (3 digits, 5 digits, and 7 digits / Invention Specification (Supplement) / 92-05 / 92104343 18 1238816 digits), (3 digits, 5 digits, and 8 digits), (3, 6 and 7 digits), (3, 6 and 8 digits), (4, 7 and 8 digits), (4, 5 and 6 digits), (4, 5 digits And 7), (4, 5 and 8), (4, 6 and 7), (4, 6 and 8), (4, 7 and 8), ( 5th, 6th and 7th), (5th, 6th and 8th), (5th, 7th and 8th), and (6th, 7 {^ and 8th) Fluoro-2-naphthyl, and 1,3,4,5,6,7,8- heptafluoro -2_ naphthyl and the like. Moreover, a preferred yellow light-emitting compound can be represented by formula (8).

However, Ri and Rla in the formula (8) are as described above. R! 3 means a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, a carboxylic acid ester group, a fluorine atom, and a carbon number of 1 to 5 (preferably 1 to 3 carbon atoms). . This R 1 3 may be bonded to a benzene nucleus', and is preferably bonded to a meta position and a para position. The plurality of R] 3 bonded to the benzene nucleus may be the same or different from each other. (8) A preferred yellow light-emitting compound can be represented by formula (8a). p! 3

312 / Invention (Supplement) / 92-05 / 921 (M343 1238816) The yellow light-emitting compound of the present invention having a structure represented by formula (1) can be considered as a lone pair with a nitrogen atom in the amine group (lone pair ) The so-called intramolecular charge movement of the 7Γ electron in the carboxyl group causes resonance stabilization and generates colored light. In addition, it is thought that if an aromatic ring represented by Ar is bonded to fluorine or contains In the case of a fluoroalkyl group (preferably a fluorinated alkyl group), the luminous brightness of a yellow light-emitting compound is enhanced by the interaction between the electron attraction of a carboxyl group and the electron attraction of a fluorine or fluorine-containing alkyl group. The yellow light-emitting compound represented by) can be produced as follows: That is, according to the reaction formula represented by formula (9), 1,4-dihydroxy-2,5-bis (ethoxyloxy) represented by formula (6) Carbonyl) benzene is reacted with an aromatic amine compound represented by the formula (7) to synthesize a dehydrated product represented by the formula (8) and then dehydrogenating the obtained dehydrated product to obtain the formula ( 1) The yellow luminescent compound shown.

1,4-dihydroxy-2,5-bis (ethoxyloxycarbonyl) represented by the above formula (6) 312 / Description of the Invention (Supplement) / 92-05 / 92104343 20 1238816 Benzene and the formula (7) The aromatic amine compound shown can be easily reacted by heating in a solvent. Examples of the solvent include acetic anhydride, acetic acid, aromatic solvents such as benzene and toluene having a carbon number of 5 or less, 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 35 ° C., and for 1 to 2 4 hours. Regarding the produced liquid obtained after the dehydrogenation reaction, if a purification operation and a separation operation are performed according to an ordinary method, The yellow light-emitting compound represented by the following formula (1) can be obtained. The yellow light-emitting compound of the present invention is obtained by making 1,4-dihydroxy-2,5-bis (acetamidine) represented by formula (6) Carbonyl) benzene and the aromatic amine compound represented by formula (7) can be easily produced by dehydration reaction and dehydrogenation reaction, so the method for producing the yellow light-emitting compound is an industrial production method. The yellow light-emitting compound is used in a light-emitting element. 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. It is sufficient if a light-emitting layer containing the above-mentioned yellow light-emitting compound is provided between the cathode and the cathode, and various structures can be used. 312 / Invention Specification (Supplement) / 92-05 / 92104343 21 1238816 Related to the invention A yellow light-emitting element using a yellow light-emitting compound will be described with reference to the figure. FIG. 1 is a cross-sectional structure explanatory diagram of a yellow light-emitting element having a single-layer organic EL element. As shown in FIG. 1, this yellow light-emitting element A is On the substrate 1 on which the transparent electrode 2 has been formed, a light-emitting material-containing light-emitting layer 3 and an electrode layer 4 are sequentially stacked. This yellow light-emitting element A is formed by expanding the substrate to have a planar shape as a whole. If it is, a planar light-emitting lighting device is formed, and if the substrate 1 in FIG. 1 is formed into a cylindrical shape to form a tubular shape as a whole, a tubular light-emitting lighting device that emits 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. The substrate 1 only needs to form a transparent electrode 2 on its surface, and a well-known substrate may 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 is formed on the surface, etc. The substrate 1 is opaque. In this case, the yellow light emitting element belongs to 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 the substrate 1 side and the back side of the yellow light emitting element. A double-sided lighting device that emits yellow light. 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, which can be used. Various materials. Specifically, the transparent electrode 2 can be made of ITO, ln203, Sn02, ZnO, CdO, and other inorganic transparent conductive materials, and conductive polymer materials such as polyaniline. 22 312 / Invention Specification (Supplement) / 92-05 / 92104343 1238816 etc. The transparent electrode 2 is formed on the substrate 1 by using a chemical vapor deposition method, a spray pyrolysis method, a vacuum evaporation method, an electron beam evaporation method, a sprinkler method, an ion beam, a base ore method, and an ion ore. It can be formed by the method, ion assist, or other methods. In addition, when the substrate is formed using an opaque member, the electrode formed on the substrate need not necessarily 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, polyfluorene, 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 light-emitting compound in the polymer film is usually 0.0 1 to 2% by weight, and preferably 0.0 5 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 light emitted will be insufficient. If the thickness of the polymer film is too thick, the driving voltage will be too high. 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 / Instruction Manual (Supplement) / 92-05 / 92104343 23 1238816 〇 . 1 ~ 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. The 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 oxide bromide, 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) triphenyl Amine), phthalocyanine, polyaniline, polythiophene derivatives, inorganic oxides (such as: molybdenum oxide, ruthenium oxide, vanadium oxide), lithium fluoride, etc. These buffer layers can be selected by appropriate materials. Reducing the driving voltage of the organic EL element that belongs to the yellow light-emitting element can improve the quantum efficiency of light emission and achieve the effect of improving the luminous brightness. In this way, the yellow light-emitting element shown in FIG. 1 containing a fluorescent compound that emits yellow light is included in the light-emitting layer. If the current is applied to the transparent electrode 2 and the electrode layer 4, yellow light will be emitted. If the light-emitting system applies an electric field between the transparent electrode 2 and the electrode layer 4, when it is planted from one side of the electrode layer 4, The electrons are implanted into the positive hole from the transparent electrode 2, and the electrons are combined with the positive hole in the light-emitting layer 3, so that the energy level 312 / Invention Specification (Supplement) / 92-05 / 921 〇43 汜 24 1238816 When the conduction band returns to the valence band, energy is generated The phenomenon that will be released in the form of light. If the yellow light-emitting element A shown in Figure 1 is set to a large area and a flat shape, it can be installed on, for example, a wall surface or a ceiling to form a large-area wall surface that emits yellow light. Element, or large-area ceiling yellow light-emitting element. That is, this yellow light-emitting element can be used as a surface light source instead of a point light source such as a conventional fluorescent lamp or an electric light bulb. Especially, it is used in homes, offices, etc. , Or the wall surface, ceiling, or floor of a vehicle, etc., you can use this yellow light-emitting element as a surface light source to illuminate or illuminate. In addition, you can also use this yellow light-emitting element A in, for example, a computer display screen. , Backlight of mobile phone display screen, digital display screen of currency register, etc. In addition, this yellow light-emitting element A can be used as various light sources such as direct lighting and indirect lighting, and it can also emit light at night for discernibility. The best advertising devices, road marking devices, and lighted notice boards can be used for lights such as brake lights for automobiles. At the same time, because 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. This yellow light-emitting element A can be formed into a tubular substrate 1 and a transparent electrode 2, a light-emitting layer 3, and an electrode layer 4 can be sequentially laminated on the inner surface side of the substrate 1 to form a tubular light-emitting body. Because this yellow The light-emitting element A does not use mercury, so it can replace the conventional fluorescent lamp that uses mercury to form a light source with good environmental protection. Second, the second example of the yellow light-emitting element of the present invention is shown. Figure 2 is a 312 / invention specification (Supplement) / 92-〇5 / 921 (M343 25 1238816) A cross-sectional explanatory view of a yellow light-emitting element of a multilayer organic EL element. As shown in FIG. 2, 'this yellow light-emitting element b is formed on the surface of the substrate 1', and 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 are sequentially stacked. 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. Examples of the hole-transporting substance contained in the hole-transporting layer 5 include triphenylamine-based compounds (eg, N, N'-diphenyl-N, N'-bis (m-tolyl)- Benzidine (TPD), a-NPD, etc.), actinides, stilbene compounds, complex ring compounds, π-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) Group-2, -fluorenoxazolyl) thiophene and the like. In addition, as the electron-transporting substance, metal complex materials such as aluminum quinolinol complex (Alq3) and benzoquinolinol beryllium complex (Bebq2) are preferably used. 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 known multilayer organic EL device. The yellow light-emitting element B shown in FIG. 2 generates yellow light emission as shown in FIG. 1 312 / Explanation of the Invention (Supplement) / 92-05 / 92104343 26 1238816 The element A 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 that is not 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 above-mentioned yellow light-emitting element B. 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 laminated 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. , The yellow light-emitting compound of the present invention as a guest pigment, and a double-layer pigment-doped light-emitting element containing a light-emitting layer for a host pigment); a layer is laminated between the anode and the cathode A hole-transporting layer containing a hole-transporting substance, and an electron-transporting light-emitting layer in which the yellow light-emitting compound of the present invention and an electron-transporting substance are co-evaporated. Between the anode and the cathode, a hole transporting layer, a secondary pigment, and an electrode containing a yellow pigment of the present invention 312 / Invention Specification (Supplement) / 92-05 / 92104343 27 1238816 and a primary pigment are laminated. 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 〇1. 20% by weight can produce white light emission with high luminance. The light-emitting layer preferably contains red decene as a sensitizer, and particularly preferably one containing 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, or as a pulse-driven organic EL element or 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 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 represented by the general formula (10). 312 / Invention Specification (Supplement) / 92-05 / 92104343 28-(10) 1238816

When the light-emitting element of the present invention emits white light, the mixing ratio between the yellow light-emitting compound and the blue light-emitting compound in the light-emitting layer is generally set to a weight ratio of 5 to 200: 1 0 to 1 00: 5 0 to 20000, preferably 10 to 100: 50 to 500: 100 to 10,000 ° Light emitting elements emitting yellow light and light emitting elements emitting white light can be used for lighting devices such as fluorescent lamps, display devices, and the like. (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-cyclohexanedione were poured. 6.4 g of -2,5-dicarboxylic acid ester, 120 m of ethanol and 120 m of acetic acid were heated in a flask to 80 ° C with a silicon bath, and the reaction was carried out by stirring at this temperature for 8 hours. Then, the contents were cooled and filtered with a nutsche, 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 Figures 5 and 6, respectively. From the IR and NMR charts, it was confirmed that 312 / Invention Specification (Supplement) / 92-05 / 92104343 29 1238816 This yellow powder had a structure represented by the formula (11).

2. Dehydrogenation reaction: 0.3 g of the yellow powder obtained by the above dehydration reaction was put into a 500 ml three-necked round bottom flask, and then 200 ml of 0-dichlorobenzene and 0.02 g of concentrated sulfuric acid were added. The contents of the flask were heated to 150 ° C. using a sand bath, and the contents were stirred at this temperature for 5 hours 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 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 Formula (1 2).

30 1238816 < Luminescence characteristics 1 > After the ITO substrate (50x50mm, manufactured by Sanyo Vacuum Industry Co., Ltd.) was ultrasonically washed in acetone for 10 minutes, it was further subjected to 2-propanol for 1 The ultrasonic wave was washed for 0 minutes, and then dried by blowing nitrogen gas. 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 (strand), wavelength: 25 4nm). The cleaned ITO substrate was installed in a vacuum evaporation device (Ta Ya Vacuum Technology Co., Ltd., UDS-M2-46 type), and a-was laminated under a pressure of 4xl (lower pressure than T6torr)- NPD layer 44nm, and a layer 411 ^ 1 formed by doping the above-mentioned yellow light-emitting compound (Formula (12)) 2.6% in Y ^ 3, and finally an aluminum alloy electrode (Al: Li = 99: l The weight ratio and the thickness of the high-purity chemical laboratory (made by the company) are 150 nm, and a yellow light-emitting element with a laminated structure shown in FIG. 1 is obtained. In addition, the vapor-deposited layer of the yellow light-emitting compound and the DPVBi layer are formed in FIG. Light-emitting layer 3. With regard to this yellow light-emitting element, the brightness and chromaticity were measured with the gradual increase of the voltage of BM-7 Fast manufactured by Debcom (stock). As a result, at a voltage of 14 V and a current of 46.4 mA The results were obtained with a luminance of 73,900 Cd / m2, a chroma X of 0.41, and a chroma Y of 0.57. ≪ Luminescence characteristic 2 > In a 5 ml simple flask, weigh 70 mg of polyvinylcarbazole, 2,5-double (1-naphthyl) -1,3,4-oxadiazole (BND) 29.7 mg and 0.3 mg of yellow powder represented by the above formula (12), and dichloroethane was added to prepare 5 ml of a solution containing a yellow light-emitting compound. This solution containing a yellow light-emitting compound was subjected to an ultrasonic wave 312 / Invention Manual for 20 minutes by using an ultrasonic cleaner (manufactured by Aisinudi Co., Ltd., US-2). (Supplement) / 92 · 05/92104343 31 1238816, and it is sufficiently uniform. The ITO substrate (50 x 50 mm, IT 0 transparent electrode thickness 200 μm, Sanrong Vacuum Industry Co., Ltd.) 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. Then, the light surface processor (wavelength 25 4nm) was used for the cleaning. Wash with 5 minutes of UV irradiation. Using a spin coater (1H-D 7 manufactured by Mikasa Co., Ltd.), the prepared yellow-containing light-emitting compound was dropped on the washed and dried ITO substrate. The solution was spin-coated with a number of revolutions of 1,500 rpin and a rotation time of 3 seconds to form a film having a dry film thickness of 100 μm. The substrate after the film formation was subjected to a constant temperature bath at 50 ° C for 3 hours. After 0 minutes of drying, use a vacuum evaporation device (Daya Vacuum Technology For aluminum alloy (VDS-M2-46 type), aluminum alloy (Al: Li = 99: l weight ratio, high-purity chemical laboratory) Electrode) to produce a yellow light-emitting element having the structure shown in Fig. 2. This yellow light-emitting element was measured for luminance and chrominance using a gradual increase in 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 0.5 5 were 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 m of acetic acid were heated in the flask to 100 ° C. using a silicon bath, and stirred at this temperature for 8 hours to perform a reaction. Then, the contents of 312 / Invention (Supplement) / 92-05 / 92104343 32 1238816 are cooled and filtered with a suction filter ', and the obtained solid is washed with ethyl acetate and methanol. The washed solid was dried to obtain a yellow powder. The 1R chart and NMR chart of this powder are shown in Fig. 9 and Fig. 10, respectively. From the IR and NMR charts, 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-neck round bottom flask, and then 500 ml of 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 NM chart of the refined yellow solid are shown in Figure 11 and Figure 12 respectively. Confirmed by these results

312 / Invention (Supplement) / 92-05 / 92104343 33 • (14) 1238816 3. Light-emitting element < Light-emitting characteristics 1 > In a 5 ml simple flask, weigh 7 () mg of polyvinylcarbazole 29.7 mg of 2,5-bis (1-naphthyl) -1,3,4-oxadiazole (BND) and 0.3 mg of yellow fused substance shown by the above formula (14), and added Yiqi Yiyuan to prepare 5 ml of a solution containing a yellow luminescent compound. This yellow light-emitting compound-containing solution was sufficiently uniform by performing ultrasonic irradiation for 20 minutes using an ultrasonic cleaner (manufactured by Aisinudi Co., Ltd., U S-2). The ITO substrate (50x50mm, ITO transparent electrode thickness 200 μm, manufactured by Sanrong Vacuum Industry Co., Ltd.) was ultrasonically washed in acetone for 10 minutes, and then ultrasonically washed with 2 · propanol for 10 minutes. , And then blow in nitrogen 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 (Migasa Corporation, 1 Η-D 7), on the cleaned and dried ITO substrate, the solution containing the above-mentioned yellow light-emitting compound was dropped, and the number of revolutions was 1 Spin coating was performed at 500 rpm and a rotation time of 3 seconds to prepare a film having a dry film thickness of 100 μm. The formed substrate was dried in a constant temperature bath at 50 ° C for 30 minutes. Then, the substrate was dried using a vacuum evaporation device (Ta Ya Vacuum Technology Co., Ltd., VDS-M2-46 type). 4xl (T6torr or less, an aluminum alloy (Al: Li = 99: 1 weight ratio, high-purity chemical laboratory (made by)) electrode having a thickness of about 150 nm is vapor-deposited, and a yellow light-emitting device having a structure shown in FIG. 1 is obtained. This yellow light-emitting element was measured for brightness and chromaticity using a gradual increase in voltage of BM-7 Fast manufactured by Debcom (stock). As a result, a brightness of 2 was obtained at a voltage of 21 V and a current of 28.71 mA. 188Cd / m2, Chroma X 312 / Invention Specification (Supplement) / 92-05 / 92104343 34 1238816 is 0.42 and Chroma Y is 0.46. (Comparative Example 1) Except for the substituted yellow powder 0 · 3 mg Instead of using rubrene 0.3 mg, the rest are the same as the light-emitting characteristics 2 in Example 1 to make a yellow light-emitting element, and then the light-emitting characteristics are investigated as in Example 1. As a result, the voltage At 20.00V and current 30.35mA, the results were obtained with a luminance of i295Cd / m1 2, a chroma X of 0.43, and a chroma Y of 0.48. (Example 3) 1. Dehydration reaction In a 1,000 ml three-neck round bottom flask, 25 g of methyl 4-aminobenzoate and dimethyl-14-cyclohexanone-2,5-dicarboxylic acid were poured. 17.2 g of acid ester, 250 m of ethanol, and 250 m of acetic acid 1. The contents of this flask were heated to 丨 with a silicon bath! 5 ° C 'The reaction was stirred at this temperature for 20 hours. Then, the contents were reacted. After cooling and filtering with a glass filter, the obtained solid was washed with methanol, ethyl acetate and petroleum ether. The washed solid was dried to obtain a yellow powder. The melting of the powder The point is 2 5 6 and the IR and NMR charts are shown in Figs. 13 and 14, respectively. From the IR and NMR charts, it was confirmed that this yellow powder has a structure shown in formula (I5).

35 1. Dehydrogenation reaction 2 312 / Invention specification (Supplement) / 92-05 / 92104343 1238816 Fill 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 · 50 ml of dichlorobenzene and 0.9 g of concentrated sulfuric acid. The contents of this flask were heated to 160 t with 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. The melting point of this solid is 254 t. 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).

—C-〇ch3 • (1 6) < Light emitting characteristics > After the ITO substrate (50 × 50 mm, manufactured by Sanyo Vacuum Industry Co., Ltd.) was ultrasonically washed in acetone for 10 minutes, it was reused. 2 -Propanol was ultrasonically washed for 10 minutes, and then dried by blowing nitrogen gas. After that, UV light irradiation was performed for 5 minutes using a light surface processor (manufactured by Sun Special Light Source (strand), wavelength: 2 54nm), and then the ITO substrate was cleaned. The cleaned ITO substrate was installed in a vacuum evaporation apparatus (made by Daya Vacuum Technology Co., Ltd., UDS-M2-46 type), and laminated under a reduced pressure of 4xl (T6t0rr 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 1238816 is doped with Alq3 at a proper concentration to form a layer of 20 nm, and then the layer is formed. A 20-nm Alq3 layer was deposited, and finally an aluminum alloy electrode (Al: Li = 99: l weight ratio, high-purity chemical research institute (stock)) was deposited to a thickness of 150 nm, and the laminated structure shown in FIG. 1 was obtained. In addition, the light-emitting layer 3 in FIG. 1 is formed from the above-mentioned yellow light-emitting compound vapor-deposited layer and the DPVBi layer. In relation to this yellow light-emitting element, BM-7 Fast manufactured by Dekang Corporation is used to slowly increase the voltage. In this case, the luminance and chromaticity were measured, and the results are shown in Table 2. (Example 4) 1. Dehydration reaction In a 1,000 ml three-neck round bottom flask, 2,6-diisopropylaniline 4 was poured. (^, Dimethyl-1,4-cyclohexanone-2,5-dicarboxylic acid ester 23.4§, ethanol 205111 and acetic acid 2.5ml. The contents of this flask 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 with a glass filter, and the obtained solids were then subjected to methanol and ethyl acetate. Wash with petroleum ether. Dry the washed solid to obtain a yellow powder. The melting point of this powder is 23 6 1, and the IR and NMR charts are shown in Figure 17 and Figure 18, respectively. It was confirmed from the IR chart and the NMR chart that the yellow powder had a structure represented by the formula (17).

CH3 312 / Invention Manual (Supplement) / 92-05 / 92104343 1238816 2. Dehydrogenation reaction: Put 20 g of the yellow powder obtained by the above dehydration reaction into a 1000 ml three-neck round bottom flask, and then Add o-dichlorobenzene 5000m and concentrated sulfuric acid 0.9g. The contents of this flask were heated to 16 trc with a silicon bath, and the contents were stirred at this temperature for 1 hour to perform 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 and petroleum ether to obtain an orange solid. This solid has a melting point of 245 ° C. Sublimation refined this orange solid. The IR and NMR charts of the purified orange solids are shown in Figs. 19 and 20, respectively. From these results, it was confirmed that this orange solid has a structure represented by Formula (18). CH3—〇 C Η 2 C Η C Η 3

3 chch I CH ^

CH I CH〇 CH

ch3 chch3 / 0 —ch3 II 〇18) < Light emitting characteristics > Except replacing the yellow light-emitting compound represented by the above formula (16) and changing to the yellow light-emitting compound represented by θ (18), the rest are the same as those in the above embodiment. 3 'Investigate luminescence characteristics. The results are shown in Table 2. (Example 5) 1. Dehydration reaction In a 1,000 ml three-necked round bottom flask, 2-methoxy-5-methylbenzene 312 / invention specification (Supplement) / 92-05 / 92104343 38 1238816 amine 25§, dimethyl-1,4-cyclohexanone-2,5-dicarboxylate 18.9§, 250 ml of ethanol, and 250 m of acetic acid: 1. The contents of this flask were heated to 115 ° C using a silicon bath, and the reaction was carried out by stirring at this temperature for 3 hours. 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 ch3o

2. Dehydrogenation reaction 20 g of the yellow-orange powder obtained by the above-mentioned dehydration reaction was put into a 1000 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 20 1 ° C. Sublimation refines this orange solid 312 / Invention Specification (Supplement) / 92-05 / 92104343 39 1238816 body. IR and NMR charts of the purified orange 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).

NH

CH

, 0 — GH g (2〇) < Light emitting characteristics > Except replacing the yellow light emitting compound represented by the above formula (18) and changing to the yellow light emitting compound represented by the formula (20), the rest are the same as those in Example 3 above. Investigate the luminous characteristics. The results are shown in Table 2. (Example 6) 1. Dehydration reaction In a 1,000 ml three-necked round-bottomed flask, 25 g of 2,5-dimethylaniline and dimethyl-1,4-cyclohexanone-2,5 · dicarboxylic acid were poured. 18.9 g of acid ester, 250 m of ethanol and 250 ml of acetic acid. The contents of this flask were heated to 115 ° C in a silicon bath, and stirred at this temperature for 3 hours to effect a reaction. 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 25 and Figure 26, respectively. From this iR chart 312 / Invention specification (Supplement) / 92-05 / 92104343 40 1238816 and NMR chart, it was confirmed that this yellow powder has a structure represented by formula (2 1). ch3—〇 / ch3

• NH

CH

II 〇3 (2 1 2. Dehydrogenation reaction. 2 Og of the yellow-orange powder obtained by the above-mentioned dehydration reaction was charged into a 1,000 ml three-neck round bottom flask, and then o-dichlorobenzene 500 ml and concentrated 0.9 g of sulfuric acid. The contents of this flask were heated to 160 ° C in a silicon bath, and the contents were stirred for 1 hour at this temperature to react. Then, the contents of the flask were cooled and then evaporated. The content was concentrated by a device. The concentrate was washed with methanol and petroleum ether to obtain an orange solid. The melting point of the solid was 25 5 ° C. The orange solid was refined by sublimation. IR chart of the refined orange solid The NMR chart is shown in Figure 27 and Figure 28. From these results, it was confirmed that this orange solid has the formula (2 2).

CH3 312 / Invention Specification (Supplement) / 92-05 / 92104343 Structure 41 1238816 < Luminescence characteristics > Instead of replacing the yellow light-emitting compound represented by the above formula (20), replace it with the yellow light-emitting compound represented by the formula (22) The rest are the same as in Example 3, and the light emission characteristics were investigated. The results are shown in Table 2. Table 2 Formula (1 6) 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 / m2 8 3 700 73 3 00 69600 765 00 Chroma 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 a novel substance that can provide a high luminance and emit bright yellow light. The yellow light-emitting compound also provides a simple manufacturing method capable of being industrially manufactured, and a yellow light-emitting element having a simple structure using the yellow light-emitting compound. [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 the intermediate obtained through the dehydration reaction in Example 1. FIG. FIG. 6 is an NMR chart of the intermediate obtained through the dehydration reaction in Example 1. FIG. 7 is an IR chart of a yellow light-emitting compound obtained by a dehydrogenation reaction in Example 1. FIG. FIG. 8 is 3Π / Invention Specification (Supplement) / 92-05 / 92104343 42 I2388l6 " 9 of the yellow luminescent compound obtained by the dehydrogenation reaction in Example 1 is the IR of the intermediate obtained by the dehydration reaction in Example 2 Illustration. fRl u 10 is an NMR chart of the intermediate obtained through the dehydration reaction in Example 2. ¢ 1 1Ί ^ U is α ϋ of the yellow light-emitting compound obtained by the dehydrogenation reaction in Example 2. ^ 12 is an NMR chart of the yellow luminescent compound obtained by the dehydrogenation reaction in Example 2. _ 1 Figure 1 Figure.

3 is an IR chart of the yellow powder obtained by the dehydration reaction in Example 3. 4 is the NMR of the yellow powder obtained by the dehydration reaction in Example 3; 5 is the IR chart of the yellow light-emitting compound obtained by the dehydrogenation reaction in Example 3. ® 16 is the NMR chart of the yellow luminescent compound obtained by the dehydrogenation reaction in Example 3. FIG. 17 is an IR chart of the yellow powder obtained by the dehydration reaction in Example 4. FIG. ® 18 is the NMR chart of the yellow powder obtained by the dehydration reaction in Example 4. Fig. 19 is an IR chart of a yellow luminescent compound obtained by a dehydrogenation reaction in Example 4. ®20 is the NMR chart of the yellow luminescent compound obtained by the dehydrogenation reaction in Example 4.

FIG. 21 is an IR chart of the yellow powder obtained by the dehydration reaction in Example 5. FIG. 22 is an NMR chart of a yellow powder obtained by a dehydration reaction in Example 5. FIG. 312 / Description of the Invention (Supplement) / 92-05 / 92104343 43 1238816 Fig. 23 is an IR chart of a yellow luminescent compound obtained by the dehydrogenation reaction in Example 5. Fig. 24 is an NMR chart of the yellow luminescent compound obtained by the 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, 3b 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 / Instruction Manual (Supplement) / 92-05 / 92104343 44

Claims (1)

jI23 «8S1j6 ^ _______ Two_. Stomach, patent scope 1. A yellow light-emitting compound, shown by the following formula (1) (Wherein Ar is a group of formula (2) in formula (1), two Ars may be the same or different from each other; R1 refers to a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, and two R] may be The same or different from each other; Ria refers to nitrogen atom, alkyl group of 1 to 5 carbons, two 1113 may be the same or different;) R 3 R 5 —— (2) (wherein R 2 refers to a single bond or methylene group; R 3 refers to a hydrogen atom, a k group having a carbon number ^, U oxygen group, a residual acid ester group, or a group formed with R 4- CF2-0-CF2-; RM refers to a hydrogen atom, an alkyl'alkoxy group having a carbon number of u, a residual acid group, a fluorine atom, a cyano group, and a fluorine-containing lower alkyl group of carbon Μ, formed together with R3 -Ch-O-CF2-, or -Ch-O-CF2- formed together with R5; R5 means hydrogen atom, carbon number] ~ 5 alkyl, alkoxy, carboxylate, cyano, fluorine Atom, fluorinated lower alkyl group of "5", -CF2-〇-CF2_1 formed together with R4 formula (3); r6 is r5 45 312 / Invention Specification (Supplement) / 92-05 / 92104343! 238816 When it is a hydrogen atom, it is a hydrogen atom, a fluorinated 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 R 6 is a hydrogen atom, R 7 is a hydrogen atom, a fluorine-containing lower alkyl group having 1 to 5 carbon atoms, an alkyl group having a carbon number, a oxy group, or a carboxylic acid ester. Group, and when R6 is a group other than a hydrogen atom, it is a hydrogen atom;) (Where 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 -cf2-〇-cf2-, or -CF2-〇-CF2- formed together with r1 (); 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; 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 hydrogen removing atom Hydrogen radical 46 1238816 (where R12 refers to a fluorine atom, a cyano group, and a fluorine-containing lower alkyl group having 1 to 5 carbon atoms; k refers to an integer from 1 to 4; η refers to an integer from 1 to 3; the total number of m and k R 12 may be the same or different;) (Wherein R 12 refers to a fluorine atom, a cyano group, and a fluorine-containing lower alkyl group having 1 to 5 carbon atoms; M refers to an integer from 1 to 4 and m refers to an integer from 1 to 3; R 12 may be the same or different from each other). 2 · — · yellow luminescent compounds, as shown in formula (8), (Wherein R1 and Rla 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, or a carbon atom containing 5 Fluoro-lower alkyl; this R1 3 may be bonded to the 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 the 1,4-dihydroxy-2,5-bis (ethoxyloxycarbonyl 312 / invention) represented by formula (6) Instruction (Supplement) / 92-05 / 92104343 47 1238816 _) benzene, react with the aromatic amine compound represented by formula (7), and then dehydrogenate the obtained dehydrated product; (Wherein R1 in formula (6) refers to hydrogen ... may be the same or different from each other; Rla (7) Ar-NH (wherein Ar and R 1 a in formula (7) are as in the scope of patent application (Shown in item 1). 4. A yellow light-emitting element is provided between a pair of electrodes, and a light-emitting layer containing a yellow light-emitting compound not represented by the above formula (1) or formula (8) is provided. The element 'is a light-emitting layer containing a yellow light-emitting compound and a blue light-emitting compound represented by the above formula (1) or (8) between a pair of electrodes. 3Π / Invention Specification (Supplement) / 92-〇5 / 921 〇4343 48