TW201418247A - Organic electroluminescent element - Google Patents

Organic electroluminescent element Download PDF

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TW201418247A
TW201418247A TW102131308A TW102131308A TW201418247A TW 201418247 A TW201418247 A TW 201418247A TW 102131308 A TW102131308 A TW 102131308A TW 102131308 A TW102131308 A TW 102131308A TW 201418247 A TW201418247 A TW 201418247A
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Takeshi Ikeda
Hirokatsu Ito
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Idemitsu Kosan Co
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Abstract

This organic electroluminescent element comprises a negative electrode, a positive electrode, and one or more organic layers that are arranged between the negative electrode and the positive electrode and include at least a light emitting layer. This organic electroluminescent element is characterized in that the light emitting layer contains an anthracene derivative represented by general formula (1), and a chrysene derivative represented by general formula (21) or a substance represented by general formula (41).

Description

有機電致發光元件 Organic electroluminescent element

本發明係有關一種有機電致發光元件。 The present invention relates to an organic electroluminescent element.

使用有機物質之有機電致發光元件(以下有時簡稱為有機EL元件)可能被用於作為固體發光型之廉價之大面積全彩顯示元件的用途,且已有多種開發。一般EL元件係由發光層及夾著該發光層之一對之對向電極所構成。在兩電極間外加電場時,由陰極側被注入電子,自陽極側注入電洞。此電子在發光層中與電洞再結合,產生激發狀態,當由激發狀態返回至基底狀態時,能量係以光的方式被釋放。 An organic electroluminescence device (hereinafter sometimes simply referred to as an organic EL device) using an organic substance may be used as a solid-state light-emitting type large-area full-color display element, and has been developed in various ways. A general EL element is composed of a light-emitting layer and a counter electrode sandwiching one of the light-emitting layers. When an electric field is applied between the electrodes, electrons are injected from the cathode side, and holes are injected from the anode side. This electron recombines with the hole in the light-emitting layer to generate an excited state, and when returned from the excited state to the substrate state, the energy is released in the form of light.

以往之有機EL元件相較於無機發光二極體時,其驅動電壓較高,發光亮度或發光效率也較低。且特性劣化明顯,無法實用化。最近之有機EL元件雖有逐漸改良,但是仍需進一步之高發光效率,長壽命、色再現性等。 In the conventional organic EL device, the driving voltage is higher than that of the inorganic light-emitting diode, and the light-emitting luminance or the light-emitting efficiency is also low. Moreover, the characteristics are deteriorated significantly and cannot be put to practical use. Recently, organic EL elements have been gradually improved, but further high luminous efficiency, long life, color reproducibility, and the like are required.

藉由有機EL用發光材料之改良,有機EL元件之性能已慢慢被改善。特別是藍色有機EL元件之色純度提昇(發光波長之短波長化)係提高顯示器之顏色再現性相關的 重要技術。 The performance of the organic EL element has been gradually improved by the improvement of the luminescent material for organic EL. In particular, the color purity of the blue organic EL element is increased (short wavelength of the emission wavelength) to improve the color reproducibility of the display. Important technology.

發光層所使用的材料例,例如有文獻1(國際公開第2010/137285號)揭示具有二苯並呋喃作為取代基之蒽衍生物。文獻1中記載以該衍生物作為主體(host)材料使用的有機EL元件係以低電壓驅動,顯示短波長的藍色發光。 An example of a material used for the light-emitting layer, for example, Document 1 (International Publication No. 2010/137285) discloses an anthracene derivative having dibenzofuran as a substituent. In Document 1, it is described that an organic EL element used as a host material of the derivative is driven at a low voltage and exhibits blue light emission of a short wavelength.

但是文獻1所記載的有機EL元件,其效率及壽命仍不足,將有機EL元件用於照明裝置或顯示裝置等之電子機器的光源時,必須進一步提高效率及更長壽命化。 However, the organic EL device described in Document 1 is still insufficient in efficiency and lifetime, and when the organic EL device is used for a light source of an electronic device such as an illumination device or a display device, it is necessary to further improve efficiency and longer life.

發明概要Summary of invention

本發明之目的係提供以低電壓驅動,以高效率且長壽命發光的有機電致發光元件。 An object of the present invention is to provide an organic electroluminescence element which is driven at a low voltage and emits light with high efficiency and long life.

[1]本發明之一實施形態之一種有機電致發光元件,其特徵係具有陰極;陽極;配置於前述陰極與前述陽極之間,至少含有發光層之1層以上的有機層;前述發光層為含有以下述一般式(1)表示之蒽衍生物與以下述一般式(21)表示之衍生物。 [1] An organic electroluminescence device according to an embodiment of the present invention, comprising: a cathode; an anode; and an organic layer disposed between the cathode and the anode and containing at least one or more of the light-emitting layers; It is an anthracene derivative represented by the following general formula (1) and represented by the following general formula (21) derivative.

[前述一般式(1)中,R1~R10之任意c個係用於與L1鍵結的單鍵,未用於與L1鍵結的R1~R10各自為選自氫原子、鹵素原子、羥基、氰基、取代或無取代之胺基、取代或無取代之碳數1~20之烷基、取代或無取代之碳數1~20之烷氧基、取代或無取代之形成環之碳數6~30之芳氧基、取代或無取代之形成環之碳數6~30之芳硫基、取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基之任一,L1係選自單鍵或連結基之任一,前述連結基係取代或無取代之形成環之碳數6~30之(a+1)價之芳香族烴基、取代或無取代之形成環之原子數5~30之(a+1)價之雜環基、或前述取代或無取代之形成環之碳數6~30之芳香族烴基及前述取代或無取代之形成環之原子數5~30之雜環基所選出之基團2~4個鍵結形成之(a+1)價基團。 [In the above general formula (1), any of R 1 ~ R 10 c departments for bonded to L 1 is a single bond, is not used to L 1 bonded to R 1 ~ R 10 are each selected from a hydrogen atom , halogen atom, hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted The aryloxy group having 6 to 30 carbon atoms forming a ring, the substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms forming a ring, Or a substituted or unsubstituted heterocyclic group having 5 to 30 atomic number of the ring forming ring, and L 1 is selected from any one of a single bond or a linking group, and the number of carbon atoms forming the ring in which the above linking group is substituted or unsubstituted 6 to 30 (a+1) of an aromatic hydrocarbon group, a substituted or unsubstituted ring-forming atomic group having 5 to 30 (a+1)-valent heterocyclic group, or the aforementioned substituted or unsubstituted ring forming ring An aromatic hydrocarbon group having 6 to 30 carbon atoms and a (a+1)-valent group formed by a bond of 2 to 4 groups selected from the above-mentioned substituted or unsubstituted heterocyclic group having 5 to 30 atomic number of the ring-forming ring.

a、b、c各自表示1~4之整數。 a, b, and c each represent an integer of 1 to 4.

Z1係以下述一般式(2)表示。] Z 1 is represented by the following general formula (2). ]

[前述一般式(2)中,X1係選自氧原子或硫原子之任一。 [In the above general formula (2), X 1 is selected from any of an oxygen atom or a sulfur atom.

R111~R118各自與前述一般式(1)中,未用於與L1鍵結的R1~R10同義。 R 111 to R 118 are each synonymous with R 1 to R 10 which are not used for bonding with L 1 in the above general formula (1).

但是R111與R112、R112與R113、R113與R114、R115與R116、R116與R117或R117與R118之中至少1組之鄰接的2個取代基,互相鍵結形成以下述一般式(3)或(4)表示之環。] However, two substituents adjacent to at least one of R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , R 115 and R 116 , R 116 and R 117 or R 117 and R 118 are mutually The bond forms a ring represented by the following general formula (3) or (4). ]

[前述一般式(3)中,y1、y2表示選自前述一般式(2)之R111~R118的鍵結位置。 [In the above general formula (3), y 1 and y 2 represent a bonding position selected from R 111 to R 118 of the above general formula (2).

前述一般式(4)中,y3、y4表示選自前述一般式(2)之R111~R118的鍵結位置。 In the above general formula (4), y 3 and y 4 represent a bonding position selected from R 111 to R 118 of the above general formula (2).

R121~R124、R125~R128各自與前述一般式(1)中,未用於與L1鍵結之R1~R10同義。 R 121 to R 124 and R 125 to R 128 are each synonymous with R 1 to R 10 which are not used for bonding with L 1 in the above general formula (1).

X2係選自氧原子或硫原子之任一。 X 2 is selected from any of an oxygen atom or a sulfur atom.

前述一般式(2)中,未形成環之R111~R118及前述一般 式(3)之R121~R124之任一個或前述一般式(2)中,未形成環之R111~R118及前述一般式(4)之R125~R128之任一個為單鍵,用於與前述一般式(1)之L1鍵結。] In the above general formula (2), R 111 to R 118 which does not form a ring, and R 121 to R 124 of the above general formula (3) or R 111 to R which do not form a ring in the above general formula (2) 118 and any one of R 125 to R 128 of the above general formula (4) are a single bond for bonding to L 1 of the above general formula (1). ]

[前述一般式(21)中,R20~R29各自表示氫原子、鹵素原子、氰基、取代或無取代之碳數1~20之烷基、取代或無取代之甲矽烷基(silyl)、或取代或無取代之形成環之碳數6~30之芳香族烴基。 [In the above general formula (21), R 20 to R 29 each represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted meyl group (silyl). Or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms forming a ring.

Ar21~Ar24各自表示取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基。 Ar 21 to Ar 24 each represent a substituted or unsubstituted ring-forming aromatic hydrocarbon group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

Ar21~Ar24具有烷基作為取代基時,各自至少具有2個以上之烷基]。 When Ar 21 to Ar 24 have an alkyl group as a substituent, each has at least two or more alkyl groups].

[2]本發明之另一實施形態之有機電致發光元件,其特徵係具有陰極;陽極;配置於前述陰極與前述陽極之間,至少含有發光層之1層以上的有機層;前述發光層為含有以前述一般式(1)表示之蒽衍生物與以下述一般式(41)表示之芘衍生物。 [2] An organic electroluminescence device according to another embodiment of the present invention, comprising: a cathode; an anode; an organic layer disposed between the cathode and the anode and containing at least one or more of the light-emitting layers; and the light-emitting layer It is an anthracene derivative represented by the above general formula (1) and an anthracene derivative represented by the following general formula (41).

[前述一般式(41)中,R21~R28各自獨立為氫原子、鹵素原子、氰基、取代或無取代之碳數1~20之烷基、取代或無取代之甲矽烷基(silyl)、或取代或無取代之形成環之碳數6~30之芳香族烴基,Ar21~Ar24各自表示取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基。 [In the above general formula (41), R 21 to R 28 are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted methyroalkyl group (silyl). Or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and Ar 21 to Ar 24 each represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms forming a ring, or a substituted or a A heterocyclic group substituted with 5 to 30 atoms forming a ring.

但是前述一般式(41)中,Ar21~Ar24之中,至少1個為以下述式(42)表示之雜環基。] In the above general formula (41), at least one of Ar 21 to Ar 24 is a heterocyclic group represented by the following formula (42). ]

[前述一般式(42)中,R211~R217各自表示氫原子、鹵素原子、氰基、取代或無取代之碳數1~20之烷基、取代或無取代之碳數2~20之烯基、取代或無取代之碳數2~20之炔基、取代或無取代甲矽烷基、 取代或無取代之形成環之碳數6~30之芳香族烴基或取代或無取代之形成環之原子數5~30之雜環基。 [In the above general formula (42), R 211 to R 217 each represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted carbon number of 2 to 20; Alkenyl, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted metaalkyl group, substituted or unsubstituted ring-forming aromatic hydrocarbon group having 6 to 30 carbon atoms or substituted or unsubstituted ring forming ring A heterocyclic group having 5 to 30 atoms.

又,R211與R212、R212與R213、R213與R214、R215與R216、及R216與R217彼此鍵結可形成飽和或不飽和的環,此等之環可被取代。 Further, R 211 and R 212 , R 212 and R 213 , R 213 and R 214 , R 215 and R 216 , and R 216 and R 217 are bonded to each other to form a saturated or unsaturated ring, and the rings may be Replace.

X21係選自氧原子或硫原子之任一。 X 21 is selected from any of an oxygen atom or a sulfur atom.

y21係與前述一般式(41)之氮原子鍵結的單鍵]。 Y 21 is a single bond bonded to the nitrogen atom of the above general formula (41)].

[3]前述本發明之有機電致發光元件,其中前述一般式(1)中之Z1較佳為以下述一般式(5)~(7)之任一表示者。 [3] The organic electroluminescence device of the present invention, wherein Z 1 in the above general formula (1) is preferably represented by any one of the following general formulas (5) to (7).

[前述一般式(5)~(7)中,R131~R140、R141~R150、R151~R160各自與前述一般式(1)中,未用於與L1鍵結之R1~R10同義。 [In the above general formulas (5) to (7), R 131 to R 140 , R 141 to R 150 , and R 151 to R 160 are each not in the above general formula (1), and are not used for bonding to L 1 . 1 ~ R 10 is synonymous.

但是R131~R140之任一、R141~R150之任一、R151~R160之任一係用於與L1鍵結,而用於與L1鍵結之基團為單鍵。 However, any one of R 131 to R 140 , any of R 141 to R 150 , and any of R 151 to R 160 are used for bonding with L 1 , and the group for bonding with L 1 is a single bond. .

X1、X2各自與前述一般式(2)中之X1、前述一般式(4)中之X2同義。X1與X2係相同或相異]。 X 1, X 2 are each the aforementioned general formula X 1 (2) in the foregoing in the general formula (4) X 2 are synonymous. X 1 and X 2 are the same or different].

[4]前述本發明之有機電致發光元件,其中前述一般式(1)中之Z1較佳為以下述一般式(8)~(10)之任一表示者。 [4] The organic electroluminescence device of the present invention, wherein Z 1 in the above general formula (1) is preferably represented by any one of the following general formulas (8) to (10).

[前述一般式(8)~(10)中,R161~R170、R171~R180、R181~R190各自與前述一般式(1)中,未用於與L1鍵結之R1~R10同義。 [In the above general formulas (8) to (10), R 161 to R 170 , R 171 to R 180 , and R 181 to R 190 each are the same as those in the above general formula (1), which are not used for bonding with L 1 . 1 ~ R 10 is synonymous.

但是R161~R170之任一、R171~R180之任一、R181~R190之任一係用於與L1鍵結,而用於與L1鍵結之基團為單 鍵。 However, any of R 161 to R 170 , any of R 171 to R 180 , and any of R 181 to R 190 are used for bonding with L 1 , and the group for bonding with L 1 is a single bond. .

X1係與前述一般式(2)中之X1同義]。 The X 1 system is synonymous with X 1 in the above general formula (2)].

[5]前述本發明之有機電致發光元件,其中前述一般式(1)之b較佳為1。 [5] The above organic electroluminescence device of the present invention, wherein b of the above general formula (1) is preferably 1.

[6]前述本發明之有機電致發光元件,其中前述一般式(1)之a較佳為1或2。 [6] The above organic electroluminescence device of the present invention, wherein a of the above general formula (1) is preferably 1 or 2.

[7]前述本發明之有機電致發光元件,其中前述一般式(1)之R9及R10之至少任一為用於與L1鍵結的單鍵較佳。 [7] The organic electroluminescence device of the present invention, wherein at least one of R 9 and R 10 of the above general formula (1) is preferably a single bond for bonding with L 1 .

[8]前述本發明之有機電致發光元件,其中前述一般式(1)之R9較佳為選自取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基之基團。 [8] The above organic electroluminescence device of the present invention, wherein R 9 of the above general formula (1) is preferably an aromatic hydrocarbon group selected from a substituted or unsubstituted ring-forming carbon number of 6 to 30, or substituted or absent. A group substituted with a heterocyclic group having 5 to 30 atoms in the ring.

[9]前述本發明之有機電致發光元件,其中X1及X2較佳為氧原子。 [9] The above organic electroluminescence device of the invention, wherein X 1 and X 2 are preferably an oxygen atom.

[10]前述本發明之有機電致發光元件,其中前述一般式(8)~(10)中,R161~R164之任一、R171~R174之任一、R181~R184之任一為用於與L1鍵結,且用於與L1鍵結的基團為單鍵較佳。 [10] The organic electroluminescence device of the present invention, wherein any one of R 161 to R 164 , any of R 171 to R 174 , and R 181 to R 184 in the above general formulas (8) to (10) Any one for bonding to L 1 and a group for bonding to L 1 is preferably a single bond.

[11]前述本發明之有機電致發光元件,其中前述一般式(1)表示之蒽衍生物較佳為以下述一般式(15)~(20)之任一表示者。 [11] The organic electroluminescence device of the present invention, wherein the anthracene derivative represented by the above general formula (1) is preferably represented by any one of the following general formulas (15) to (20).

[前述一般式(15)~(20)中之R161~R190各自與前述一般式(1)中之R1~R8同義。 [R 161 to R 190 in the above general formulas (15) to (20) are each synonymous with R 1 to R 8 in the above general formula (1).

前述一般式(15)~(20)中之X1係與前述一般式(2)中之X1同義]。 The X 1 in the above general formulas (15) to (20) is synonymous with X 1 in the above general formula (2)].

[12]前述本發明之有機電致發光元件,其中前述一般式(1)表示之蒽衍生物,較佳為以下述一般式(51)~(56)之任一表示者。 [12] The organic electroluminescence device of the present invention, wherein the anthracene derivative represented by the above general formula (1) is preferably represented by any one of the following general formulas (51) to (56).

[前述一般式(51)~(56)中之R161~R190係與前述一般式(1)中之R1~R8同義。 [R 161 to R 190 in the above general formulas (51) to (56) are synonymous with R 1 to R 8 in the above general formula (1).

前述一般式(51)~(56)中之X1係與前述一般式(2)中之X1同義]。 The X 1 in the above general formulas (51) to (56) is synonymous with X 1 in the above general formula (2)].

[13]前述本發明之有機電致發光元件,其中前述一般式(1)表示之蒽衍生物,較佳為以下述一般式(57)~(62)之任一表示者。 [13] The organic electroluminescence device of the present invention, wherein the anthracene derivative represented by the above formula (1) is preferably represented by any one of the following general formulas (57) to (62).

[前述一般式(57)~(62)中之R161~R190係與前述一般式(1)中之R1~R8同義。 [R 161 to R 190 in the above general formulas (57) to (62) are synonymous with R 1 to R 8 in the above general formula (1).

前述一般式(57)~(62)中之X1係與前述一般式(2)中之X1同義]。 The X 1 in the above general formulas (57) to (62) is synonymous with X 1 in the above general formula (2)].

[14]前述本發明之有機電致發光元件,其中前述一般式(21)之R20~R29較佳為氫原子。 [14] The organic electroluminescence device of the present invention, wherein R 20 to R 29 of the above general formula (21) are preferably a hydrogen atom.

[15]前述本發明之有機電致發光元件,其中前述一般式(41)之Ar21及Ar23較佳為前述一般式(42)表示之雜環基。 [15] The organic electroluminescence device of the present invention, wherein Ar 21 and Ar 23 of the above general formula (41) are preferably a heterocyclic group represented by the above general formula (42).

[16]前述本發明之有機電致發光元件,其中前述一般式(41)之R21~R28較佳為氫原子。 [16] The organic electroluminescence device of the present invention, wherein R 21 to R 28 of the above general formula (41) are preferably a hydrogen atom.

[17]前述本發明之有機電致發光元件,其中前述一般 式(41)之R22及R26較佳為取代或無取代之碳數1~20之烷基、或取代或無取代之碳數3~30之烷基甲矽烷基,前述一般式(41)之R21、R23、R24、R25、R27、及R28為氫原子。 [17] The above organic electroluminescent device of the present invention, wherein R 22 and R 26 of the above general formula (41) are preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted carbon. The alkylmercaptoalkyl group having 3 to 30 atoms, and R 21 , R 23 , R 24 , R 25 , R 27 and R 28 in the above general formula (41) are a hydrogen atom.

[18]前述本發明之有機電致發光元件,其中前述一般式(42)之X21較佳為氧原子。 [18] The above organic electroluminescence device of the present invention, wherein X 21 of the above general formula (42) is preferably an oxygen atom.

1‧‧‧陰極 1‧‧‧ cathode

2‧‧‧電子輸送層 2‧‧‧Electronic transport layer

3‧‧‧發光層 3‧‧‧Lighting layer

4‧‧‧電洞輸送層 4‧‧‧ hole transport layer

5‧‧‧陽極 5‧‧‧Anode

6‧‧‧基板 6‧‧‧Substrate

圖1係表示本發明之實施形態之有機電致發光元件之一例的概略構成圖。 Fig. 1 is a schematic configuration diagram showing an example of an organic electroluminescence device according to an embodiment of the present invention.

<第1實施形態> <First embodiment> (有機EL元件之元件構成) (Elements of organic EL elements)

以下說明本發明之一實施形態之有機EL元件之元件構成。 The element configuration of the organic EL device according to an embodiment of the present invention will be described below.

本實施形態之有機EL元件係在一對電極間具備有機層。此有機層係具有至少一層以有機化合物所構成的層。有機層也可含有無機化合物。 The organic EL device of the present embodiment includes an organic layer between a pair of electrodes. The organic layer has at least one layer of an organic compound. The organic layer may also contain an inorganic compound.

本實施形態之有機EL元件中,有機層中之至少1層具有發光層。因此,有機層例如可以一層發光層所構成,亦可具有電洞注入層、電洞輸送層、電子注入層、電子輸 送層、電洞障壁層、電子障壁層等公知之有機EL元件所採用的層。 In the organic EL device of the present embodiment, at least one of the organic layers has a light-emitting layer. Therefore, the organic layer may be composed of, for example, a light-emitting layer, or may have a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport. A layer used for a known organic EL element such as a layer, a hole barrier layer, or an electron barrier layer.

有機EL元件之代表的元件構成,例如有 The component composition of the organic EL element, for example,

(a)陽極/發光層/陰極 (a) anode / luminescent layer / cathode

(b)陽極/電洞注入‧輸送層/發光層/陰極 (b) Anode/hole injection ‧ Transport layer / luminescent layer / cathode

(c)陽極/發光層/電子注入‧輸送層/陰極 (c) Anode / luminescent layer / electron injection ‧ transport layer / cathode

(d)陽極/電洞注入‧輸送層/發光層/電子注入‧輸送層/陰極 (d) Anode/hole injection ‧ Transport layer / luminescent layer / Electron injection ‧ Transport layer / Cathode

(e)陽極/電洞注入‧輸送層/發光層/障壁層/電子注入‧輸送層/陰極等的構造。 (e) Anode/hole injection ‧ transport layer / luminescent layer / barrier layer / electron injection ‧ transport layer / cathode, etc.

上述之中,較佳係使用(d)之構成,但當然不受限於此等者。 Among the above, the configuration of (d) is preferably used, but it is of course not limited thereto.

此外,上述「發光層」係指具有發光功能之有機層,且採用摻雜系統時,包含主體(host)材料與摻雜劑材料。此時,主體材料主要係促進電子與電洞之再結合,且具有將激子封閉於發光層內之功能,摻雜劑材料係具有使再結合所得之激子有效率地發光的功能。磷光元件時,主體材料主要係具有將摻雜劑所生成之激子封閉於發光層內的功能。 In addition, the above-mentioned "light-emitting layer" means an organic layer having a light-emitting function, and when a doping system is employed, a host material and a dopant material are included. At this time, the host material mainly promotes recombination of electrons and holes, and has a function of enclosing excitons in the light-emitting layer, and the dopant material has a function of efficiently emitting excitons obtained by recombination. In the case of a phosphorescent element, the host material mainly has a function of enclosing excitons generated by the dopant in the light-emitting layer.

上述「電洞注入‧輸送層」係指「電洞注入層及電洞輸送層中之至少任一者」,「電子注入‧輸送層」係指「電子注入層及電子輸送層中之至少任一者」。在此,具有電洞注入層及電洞輸送層時,在陽極側設置電洞注入層為佳。又,具有電子注入層及電子輸送層時,在陰極側設 置電子注入層為佳。 The above-mentioned "hole injection ‧ transport layer" means "at least one of the hole injection layer and the hole transport layer", and "electron injection ‧ transport layer" means "at least one of the electron injection layer and the electron transport layer" One." Here, when the hole injection layer and the hole transport layer are provided, it is preferable to provide a hole injection layer on the anode side. Moreover, when the electron injecting layer and the electron transporting layer are provided, the cathode side is provided It is preferable to place an electron injecting layer.

本實施形態中,電子輸送層係指存在於發光層與陰極之間之電子輸送區域的有機層中,電子移動度最高之有機層。電子輸送區域為以單層所構成時,該層即為電子輸送層。又,磷光型之有機EL元件中,如構成(e)所示,以防止發光層所生成之激發能量之擴散為目的,有時在發光層與電子輸送層之間採用電子移動度不一定不高之障壁層,且鄰接於發光層之有機層並不一定相當於電子輸送層。 In the present embodiment, the electron transporting layer means an organic layer having the highest electron mobility among the organic layers existing in the electron transporting region between the light emitting layer and the cathode. When the electron transporting region is composed of a single layer, the layer is an electron transporting layer. Further, in the phosphorescent organic EL device, as shown in the configuration (e), in order to prevent the diffusion of the excitation energy generated by the light-emitting layer, the electron mobility may not necessarily be between the light-emitting layer and the electron transport layer. The high barrier layer and the organic layer adjacent to the light-emitting layer do not necessarily correspond to the electron transport layer.

圖1係表示本實施形態中之有機EL元件之一例的概略構成。 Fig. 1 is a view showing a schematic configuration of an example of an organic EL device in the present embodiment.

有機EL元件1係具有透光性之基板2、陽極3、陰極4、配置於陽極3與陰極4之間的有機層10。 The organic EL element 1 is a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4.

有機層10具有含主體材料及摻雜劑材料的發光層5。又,有機層10係於發光層5與陽極3之間,具有電洞輸送層6。此外,有機層10係在發光層5與陰極4之間具有電子輸送層7。 The organic layer 10 has a light-emitting layer 5 containing a host material and a dopant material. Further, the organic layer 10 is provided between the light-emitting layer 5 and the anode 3, and has a hole transport layer 6. Further, the organic layer 10 has an electron transport layer 7 between the light-emitting layer 5 and the cathode 4.

(發光層) (lighting layer)

本實施形態之有機EL元件中,發光層中含有以下述一般式(1)表示之蒽衍生物、及以下述一般式(21)表示之衍生物。 In the organic EL device of the present embodiment, the luminescent layer contains an anthracene derivative represented by the following general formula (1) and is represented by the following general formula (21). derivative.

.主體材料 . Body material

本實施形態之有機EL元件中,可使用以下述一般式(1)表示之蒽衍生物作為主體材料。 In the organic EL device of the present embodiment, an anthracene derivative represented by the following general formula (1) can be used as a host material.

前述一般式(1)中,R1~R10之任c個係用於與L1鍵結的單鍵,未用於與L1鍵結的R1~R10各自為選自氫原子、鹵素原子、羥基、氰基、取代或無取代之胺基、取代或無取代之碳數1~20之烷基、取代或無取代之碳數1~20之烷氧基、取代或無取代之形成環之碳數6~30之芳氧基、取代或無取代之形成環之碳數6~30之芳硫基、取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基之任一。 The foregoing general formula (1), any one of R 1 ~ R 10 c departments for a single bond and L 1 bond to the junction, the junction is not used, R 1 and L key 1 ~ R 10 are each selected from a hydrogen atom, Halogen atom, hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted An aryloxy group having 6 to 30 carbon atoms in the ring, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms forming a ring, or Any one of substituted or unsubstituted heterocyclic groups of 5 to 30 atoms forming a ring.

L1係選自單鍵或連結基之任一,前述連結基係取代或無取代之形成環之碳數6~30之(a+1)價之芳香族烴基、取代或無取代之形成環之原子數5~30之(a+1)價之雜環基、或前述取代或無取代之形成環之碳數6~30之芳香族烴基及前述取代或無取代之形成環之原子數5~30之雜環基所選出之基團2~4個鍵結形成之 (a+1)價基團。 L 1 is selected from any one of a single bond or a linking group, and the above-mentioned linking group is substituted or unsubstituted to form a ring having a carbon number of 6 to 30 (a+1) of an aromatic hydrocarbon group, a substituted or unsubstituted ring. a heterocyclic group having an atomic number of 5 to 30 (a+1) or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms and a substituted or unsubstituted atomic number of the ring 5 The group selected from the heterocyclic group of ~30 is 2 to 4 bonded groups to form (a+1) valence groups.

a、b、c各自表示1~4之整數。 a, b, and c each represent an integer of 1 to 4.

Z1係以下述一般式(2)表示。 Z 1 is represented by the following general formula (2).

[前述一般式(2)中,X1係選自氧原子或硫原子之任一。 [In the above general formula (2), X 1 is selected from any of an oxygen atom or a sulfur atom.

R111~R118各自與前述一般式(1)中,未用於與L1鍵結的R1~R10同義。 R 111 to R 118 are each synonymous with R 1 to R 10 which are not used for bonding with L 1 in the above general formula (1).

但是R111與R112、R112與R113、R113與R114、R115與R116、R116與R117或R117與R118之中至少1組之鄰接的2個取代基,互相鍵結形成以下述一般式(3)或(4)表示之環。 However, two substituents adjacent to at least one of R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , R 115 and R 116 , R 116 and R 117 or R 117 and R 118 are mutually The bond forms a ring represented by the following general formula (3) or (4).

前述一般式(3)中,y1、y2表示選自前述一般式(2)之R111~R118的鍵結位置。 In the above general formula (3), y 1 and y 2 represent a bonding position selected from R 111 to R 118 of the above general formula (2).

前述一般式(4)中,y3、y4表示選自前述一般式(2)之R111~R118的鍵結位置。 In the above general formula (4), y 3 and y 4 represent a bonding position selected from R 111 to R 118 of the above general formula (2).

R121~R124、R125~R128各自與前述一般式(1)中,未用於與L1鍵結之R1~R10同義。 R 121 to R 124 and R 125 to R 128 are each synonymous with R 1 to R 10 which are not used for bonding with L 1 in the above general formula (1).

X2係選自氧原子或硫原子之任一。 X 2 is selected from any of an oxygen atom or a sulfur atom.

前述一般式(2)中,未形成環之R111~R118及前述一般式(3)之R121~R124之任一個或前述一般式(2)中,未形成環之R111~R118及前述一般式(4)之R125~R128之任一個為單鍵,用於與前述一般式(1)之L1鍵結。 In the above general formula (2), R 111 to R 118 which does not form a ring, and R 121 to R 124 of the above general formula (3) or R 111 to R which do not form a ring in the above general formula (2) 118 and any one of R 125 to R 128 of the above general formula (4) are a single bond for bonding to L 1 of the above general formula (1).

此外,前述一般式(1)中,Z1較佳為下述一般式(5)~(7)之任一表示者。例如下述一般式(5)係前述一般式(4)之y3相當於前述一般式(2)中之R114所鍵結之碳原子的位置,y4相當於前述一般式(2)中之R113所鍵結之碳原子的位置。 Further, in the above general formula (1), Z 1 is preferably one of the following general formulas (5) to (7). For example, the following general formula (5) is that the y 3 of the above general formula (4) corresponds to the position of the carbon atom bonded by R 114 in the above general formula (2), and y 4 corresponds to the above general formula (2). The position of the carbon atom to which R 113 is bonded.

前述一般式(5)~(7)中,R131~R140、R141~R150、R151~R160各自與前述一般式(1)中,未用於與L1鍵結之R1~R10同義。 ~ In (7), R 131 ~ R 140, R 141 ~ R 150, R 151 ~ R L 1 bonded to one of R & lt foregoing general formula (5) above, respectively 160 general formula (1) is not used and ~R 10 is synonymous.

但是R131~R140之任一、R141~R150之任一、R151~R160之任一係用於與L1鍵結,而用於與L1鍵結之基團為單鍵。 However, any one of R 131 to R 140 , any of R 141 to R 150 , and any of R 151 to R 160 are used for bonding with L 1 , and the group for bonding with L 1 is a single bond. .

X1、X2各自與前述一般式(2)中之X1、前述一般式(4)中之X2同義。X1與X2係相同或相異。 X 1, X 2 are each the aforementioned general formula X 1 (2) in the foregoing in the general formula (4) X 2 are synonymous. X 1 and X 2 are the same or different.

又,前述一般式(1)中,Z1較佳為以下述一般式(8)~(10)之任一表示者。 Further, in the above general formula (1), Z 1 is preferably represented by any one of the following general formulas (8) to (10).

前述一般式(8)~(10)中,R161~R170、R171~R180、R181~R190各自與前述一般式(1)中,未用於與L1鍵結之 R1~R10同義。 In ~ (10), R 161 ~ R 170, R 171 ~ R 180, R 181 ~ R L 1 bonded to one of R & lt foregoing general formula (8) above, respectively 190 general formula (1) is not used and ~R 10 is synonymous.

但是R161~R170之任一、R171~R180之任一、R181~R190之任一係用於與L1鍵結,而用於與L1鍵結之基團為單鍵。 However, any of R 161 to R 170 , any of R 171 to R 180 , and any of R 181 to R 190 are used for bonding with L 1 , and the group for bonding with L 1 is a single bond. .

X1係與前述一般式(2)中之X1同義。 The X 1 system is synonymous with X 1 in the above general formula (2).

前述一般式(1)中之Z1特佳為以前述一般式(8)~(10)之任一表示者。 Z 1 in the above general formula (1) is particularly preferably represented by any one of the above general formulas (8) to (10).

前述一般式(1)中,b較佳為1,a較佳為1或2,a更佳為1。 In the above general formula (1), b is preferably 1, a is preferably 1 or 2, and a is more preferably 1.

前述一般式(1)之R9及R10之至少任一為用於與L1鍵結的單鍵較佳。 At least one of R 9 and R 10 of the above general formula (1) is preferably a single bond for bonding to L 1 .

此外,前述一般式(1)之R9較佳為選自取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基之基團,更佳為以下述一般式(11)表示者。 Further, R 9 of the above general formula (1) is preferably an aromatic hydrocarbon group selected from a substituted or unsubstituted ring-forming carbon number of 6 to 30, or a substituted or unsubstituted ring-forming atomic number of 5 to 30. The group of the ring group is more preferably represented by the following general formula (11).

前述一般式(11)中,Ar1表示選自取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基之基團。 In the above general formula (11), Ar 1 represents an aromatic hydrocarbon group having 6 to 30 carbon atoms selected from a substituted or unsubstituted ring, or a substituted or unsubstituted heterocyclic group having 5 to 30 atoms forming a ring. Group.

Ra各自與前述一般式(1)中,未用於與L1鍵結之R1~R10同義。 Each of Ra is synonymous with R 1 to R 10 which is not used for bonding with L 1 in the above general formula (1).

d表示1~4之整數。 d represents an integer from 1 to 4.

d為2~4時,複數之Ra係相同或相異。 When d is 2 to 4, the complex Ra is the same or different.

前述一般式(1)之R9為由此等基團所選出之基團時,前述一般式(1)之R10更佳為用於與L1鍵結的單鍵。 When R 9 of the above general formula (1) is a group selected from such a group, R 10 of the above general formula (1) is more preferably a single bond for bonding with L 1 .

此外,前述一般式(1)之R9較佳為取代或無取代之形成環之碳數10~30之縮合芳香族烴基。 Further, R 9 of the above general formula (1) is preferably a substituted or unsubstituted condensed aromatic hydrocarbon group having 10 to 30 carbon atoms forming a ring.

前述一般式(1)中,X1及X2較佳為氧原子。 In the above general formula (1), X 1 and X 2 are preferably an oxygen atom.

前述一般式(8)~(10)中,R161~R164之任一、R171~R174之任一、R181~R184之任一為用於與L1鍵結,且用於與L1鍵結的基團為單鍵較佳。 In the above general formulas (8) to (10), any one of R 161 to R 164 , any of R 171 to R 174 , and any of R 181 to R 184 are used for bonding with L 1 and used for The group bonded to L 1 is preferably a single bond.

前述一般式(1)表示之蒽衍生物,較佳為以下述一般式(15)~(20)之任一表示。 The anthracene derivative represented by the above general formula (1) is preferably represented by any one of the following general formulas (15) to (20).

前述一般式(15)~(20)中之R161~R190各自與前述一般式(1)中之R1~R8同義。 R 161 to R 190 in the above general formulas (15) to (20) are each synonymous with R 1 to R 8 in the above general formula (1).

前述一般式(15)~(20)中之X1係與前述一般式(2)中之X1同義。 The X 1 in the above general formulas (15) to (20) is synonymous with X 1 in the above general formula (2).

前述以一般式(1)表示之蒽衍生物,較佳為以下述一般式(51)~(56)之任一表示者。 The anthracene derivative represented by the general formula (1) is preferably represented by any one of the following general formulas (51) to (56).

前述一般式(51)~(56)中之R161~R190係與前述一般式(1)中之R1~R8同義。 The R 161 to R 190 in the above general formulas (51) to (56) are synonymous with R 1 to R 8 in the above general formula (1).

前述一般式(51)~(56)中之X1係與前述一般式(2)中之X1同義。 The X 1 in the above general formulas (51) to (56) is synonymous with X 1 in the above general formula (2).

前述一般式(1)表示之蒽衍生物,較佳為以下述一般 式(57)~(62)之任一表示者。 The anthracene derivative represented by the above general formula (1) is preferably as follows. Any one of the formulas (57) to (62).

前述一般式(57)~(62)中之R161~R190係與前述一般式(1)中之R1~R8同義。 R 161 to R 190 in the above general formulas (57) to (62) are synonymous with R 1 to R 8 in the above general formula (1).

前述一般式(57)~(62)中之X1係與前述一般式(2)中之X1同義。 The X 1 in the above general formulas (57) to (62) is synonymous with X 1 in the above general formula (2).

前述一般式(57)~(62)之任一表示之蒽衍生物係相當於前述一般式(15)~(20)中之L1為伸苯基的情形。前述一般式(57)~(62)中,對於該伸苯基之6員環之碳原子,蒽環與前述具有X1之縮合環產生鍵結。 The anthracene derivative represented by any one of the above general formulas (57) to (62) corresponds to a case where L 1 in the above general formulas (15) to (20) is a stretching phenyl group. In the above general formulas (57) to (62), for the carbon atom of the 6-membered ring of the phenylene group, the anthracene ring is bonded to the aforementioned condensed ring having X 1 .

前述一般式(13)~(20),(51)~(62)中,X1較佳為氧原子。 In the above general formulas (13) to (20) and (51) to (62), X 1 is preferably an oxygen atom.

其次,說明前述一般式(1)~(20),(51)~(62)所記載的各取代基。 Next, each substituent described in the above general formulas (1) to (20) and (51) to (62) will be described.

前述一般式(1)~(20),(51)~(62)所記載之取代基之具體例,例如有鹵素原子、羥基、氰基、取代或無取代之胺基、取代或無取代之碳數1~20之直鏈狀、支鏈狀或環狀之烷基、取代或無取代之碳數1~20之直鏈狀、支鏈狀或環狀之鹵烷基、取代或無取代之碳數1~20之直鏈狀、支鏈狀或環狀之烷氧基、取代或無取代之碳數1~20之直鏈狀、支鏈狀或環狀之鹵烷氧基、取代或無取代之形成環之碳數6~30之芳氧基、取代或無取代之形成環之碳數6~30之芳硫基、取代或無取代之形成環之碳數6~30之芳香族烴基、取代或無取代之形成環之原子數5~30之雜環基。 Specific examples of the substituents described in the above general formulae (1) to (20) and (51) to (62) include, for example, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, and a substituted or unsubstituted one. a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear, branched or cyclic haloalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms, substituted Or an unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring, and a carbon number of 6 to 30 A hydrocarbon group, a substituted or unsubstituted heterocyclic group having 5 to 30 atomic atoms forming a ring.

前述一般式(1)~(20),(51)~(62)中之鹵素原子,例如有氟、氯、溴、碘等,較佳為氟。 The halogen atoms in the above general formulas (1) to (20) and (51) to (62) are, for example, fluorine, chlorine, bromine, iodine or the like, preferably fluorine.

前述一般式(1)~(20),(51)~(62)中之取代或無取代之胺基,例如有被芳香族烴基取代的胺基,較佳為苯基胺基。取代胺基之芳香族烴基,例如有下述形成環之碳數6~30之芳香族烴基。 The substituted or unsubstituted amino group in the above general formulae (1) to (20), (51) to (62), for example, an amine group substituted with an aromatic hydrocarbon group, preferably a phenylamine group. The aromatic hydrocarbon group of the substituted amino group may, for example, be an aromatic hydrocarbon group having 6 to 30 carbon atoms which forms a ring.

前述一般式(1)~(20),(51)~(62)中之碳數1~20之烷基,可為直鏈、支鏈或環狀之任一,直鏈或支鏈之烷基,例如有甲基、乙基、丙基、異丙基、n-丁基、s-丁基、異丁基、t-丁基、n-戊基、n-己基、n-庚基、n-辛基、n-壬基、n-癸基、n-十一基、n-十二基、n-十三基、n-十四基、n-十五基、n-十六基、n-十七基、n-十八基、新戊 基、1-甲基戊基、2-甲基戊基、1-戊基己基、1-丁基戊基、1-庚基辛基、3-甲基戊基、羥基甲基、1-羥基乙基、2-羥基乙基、2-羥基異丁基、1,2-二羥基乙基、1,3-二羥基異丙基、2,3-二羥基-t-丁基、1,2,3-三羥基丙基、氯甲基、1-氯乙基、2-氯乙基、2-氯異丁基、1,2-二氯乙基、1,3-二氯異丙基、2,3-二氯-t-丁基、1,2,3-三氯丙基、溴甲基、1-溴乙基、2-溴乙基、2-溴異丁基、1,2-二溴乙基、1,3-二溴異丙基、2,3-二溴-t-丁基、1,2,3-三溴丙基、碘甲基、1-碘乙基、2-碘乙基、2-碘異丁基、1,2-二碘乙基、1,3-二碘異丙基、2,3-二碘-t-丁基、1,2,3-三碘丙基、胺基甲基、1-胺基乙基、2-胺基乙基、2-胺基異丁基、1,2-二胺基乙基、1,3-二胺基異丙基、2,3-二胺基-t-丁基、1,2,3-三胺基丙基、氰基甲基、1-氰基乙基、2-氰基乙基、2-氰基異丁基、1,2-二氰基乙基、1,3-二氰基異丙基、2,3-二氰基-t-丁基、1,2,3-三氰基丙基、硝基甲基、1-硝基乙基、2-硝基乙基、1,2-二硝基乙基、2,3-二硝基-t-丁基、1,2,3-三硝基丙基、三氟甲基、2,2,2-三氟乙基、1,1,1,3,3,3-六氟-2-丙基基等。 The alkyl group having 1 to 20 carbon atoms in the above general formulas (1) to (20), (51) to (62) may be any of linear, branched or cyclic, linear or branched alkyl groups. Base, for example, methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, N-octyl, n-fluorenyl, n-fluorenyl, n-undecyl, n-dodecyl, n-tridedecyl, n-tetradecyl, n-pentadecayl, n-hexadeca , n-heptadecyl, n-octadecyl, neopenta , 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl, hydroxymethyl, 1-hydroxyl Ethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-dihydroxy-t-butyl, 1,2 , 3-trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-Dichloro-t-butyl, 1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2- Dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-t-butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2- Iodine ethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl, 2,3-diiodo-t-butyl, 1,2,3-triiodide Propyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1,3-diaminoisopropyl , 2,3-Diamino-t-butyl, 1,2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanoiso Butyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-t-butyl 1,2,3-Tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 1,2-dinitroethyl, 2,3-dinitro-t -butyl, 1,2,3-trinitropropyl, trifluoromethyl, 2,2,2-trifluoroethyl, 1,1,1,3,3,3-hexafluoro-2-propane Base and so on.

環狀之烷基(環烷基),例如有環丙基、環丁基、環戊基、環己基、環辛基、4-甲基環己基、3,5-四甲基環己基、1-金剛烷基、2-金剛烷基、1-降莰基、2-降莰基等。 A cyclic alkyl group (cycloalkyl group), for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, 4-methylcyclohexyl, 3,5-tetramethylcyclohexyl, 1 - adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like.

前述烷基中,較佳為碳數1~10之烷基,更佳為碳數1~8之烷基,特佳為碳數1~4之烷基。其中,較佳為甲 基、異丙基、t-丁基、環己基。 The alkyl group is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms, particularly preferably an alkyl group having 1 to 4 carbon atoms. Among them, preferably A Base, isopropyl, t-butyl, cyclohexyl.

碳數1~20之直鏈狀、支鏈狀或環狀之鹵烷基,例如有前述碳數1~20之烷基被1個以上之鹵素原子所取代者。具體而言,例如有氟甲基、二氟甲基、三氟甲基、氟乙基、三氟甲基甲基等。 The linear, branched or cyclic haloalkyl group having 1 to 20 carbon atoms, for example, the alkyl group having 1 to 20 carbon atoms is substituted by one or more halogen atoms. Specific examples thereof include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, and a trifluoromethylmethyl group.

前述一般式(1)~(20)、(51)~(62)中之碳數1~20之直鏈狀、支鏈狀或環狀之烷氧基係以-OY1表示。此Y1之例有前述碳數1~20之烷基。烷氧基例如有甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基。 The linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms in the above general formulae (1) to (20) and (51) to (62) is represented by -OY 1 . An example of the Y 1 is an alkyl group having 1 to 20 carbon atoms. The alkoxy group is, for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group or a hexyloxy group.

上述烷氧基之中,較佳為碳數1~10之烷氧基,更佳為碳數1~8之烷氧基。特佳為碳數1~4之烷氧基。 Among the above alkoxy groups, an alkoxy group having 1 to 10 carbon atoms is preferred, and an alkoxy group having 1 to 8 carbon atoms is more preferred. Particularly preferred is an alkoxy group having 1 to 4 carbon atoms.

前述一般式(1)~(20)、(51)~(62)中之碳數1~20之直鏈狀、支鏈狀或環狀之鹵烷氧基,例如有前述碳數1~20之烷氧基被1以上之鹵基取代者。 The linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms in the above general formulas (1) to (20) and (51) to (62), for example, the above carbon number 1 to 20 The alkoxy group is substituted by a halogen group of 1 or more.

前述一般式(1)~(20)、(51)~(62)中之形成環之碳數6~30之芳氧基係以-OZ2表示。此Z2之例有下述形成環之碳數6~30之芳香族烴基。此芳氧基例如有苯氧基。 The aryloxy group having 6 to 30 carbon atoms forming a ring in the above general formulae (1) to (20) and (51) to (62) is represented by -OZ 2 . Examples of the Z 2 include the following aromatic hydrocarbon groups having 6 to 30 carbon atoms forming a ring. This aryloxy group is, for example, a phenoxy group.

前述一般式(1)~(20)、(51)~(62)中之形成環之碳數6~30之芳硫基係以-SZ3表示。此Z3之例有下述形成環之碳數6~30之芳香族烴基。 The arylthio group having 6 to 30 carbon atoms forming a ring in the above general formulas (1) to (20) and (51) to (62) is represented by -SZ 3 . Examples of the Z 3 include the following aromatic hydrocarbon groups having 6 to 30 carbon atoms forming a ring.

前述一般式(1)~(20)、(51)~(62)中之形成環之碳數6~30之芳香族烴基,例如有非縮合芳香族烴基及縮合芳香族烴基,更具體而言,例如有苯基、萘基、蒽基、菲基、聯苯基、三聯苯基、四聯苯基、熒蒽基、芘基 (pyrenyl)、聯三伸苯基(triphenylenyl)、菲基(phenanthrenyl)、茀基(fluorenyl)、9,9-二甲基茀基、苯并[c]菲基、苯并[a]聯三伸苯基、萘并[1,2-c]菲基、萘并[1,2-a]聯三伸苯基、二苯并[a,c]聯伸三苯基、苯并[b]熒蒽基等,上述芳香族烴基之中,更佳為形成環之碳數6~20之芳香族烴基,特佳為形成環之碳數6~12之芳香族烴基。又,較佳為苯基、萘基、三聯苯基、熒蒽基、9,9-二甲基茀基、苯并[c]菲基、菲基。 The aromatic hydrocarbon group having 6 to 30 carbon atoms forming a ring in the above general formulae (1) to (20) and (51) to (62), for example, a non-condensed aromatic hydrocarbon group and a condensed aromatic hydrocarbon group, more specifically For example, there are phenyl, naphthyl, anthryl, phenanthryl, biphenyl, terphenyl, tetraphenyl, fluoranthenyl, fluorenyl (pyrenyl), triphenylenyl, phenanthrenyl, fluorenyl, 9,9-dimethylindenyl, benzo[c]phenanthryl, benzo[a] Phenyl, naphtho[1,2-c]phenanthryl, naphtho[1,2-a]triphenylene, dibenzo[a,c]linked triphenyl, benzo[b]fluorene Among the above aromatic hydrocarbon groups, the aromatic hydrocarbon group having 6 to 20 carbon atoms in the ring is more preferably formed, and particularly preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms in the ring. Further, a phenyl group, a naphthyl group, a terphenyl group, a fluoranthene group, a 9,9-dimethylindenyl group, a benzo[c]phenanthrenyl group or a phenanthryl group is preferred.

前述一般式(1)~(20)、(51)~(62)中之形成環之原子數5~30之芳香族雜環基,例如有非縮合芳香族雜環及縮合芳香族雜環,更具體而言,例如有吡咯基、吡嗪基、吡啶基、吲哚基、異吲哚基、呋喃基、苯並呋喃基、異苯並呋喃基、二苯並呋喃基、二苯並噻吩基、喹啉基、異喹啉基、喹喔啉基、咔唑基、菲啶基(Phenanthridinyl)、吖啶基、菲繞啉基、噻吩基及由吡啶環、吡嗪環、嘧啶環、噠嗪環、三嗪環、吲哚環、喹啉環、吖啶環、吡咯烷環、二噁烷環、哌啶環、嗎啉環、哌嗪環、咔唑環、呋喃環、噻吩環、噁唑環、噁二唑環、苯並噁唑環、噻唑環、噻二唑環、苯並噻唑環、三唑環、咪唑環、苯並咪唑環、吡喃環、二苯並呋喃環、苯並[c]二苯並呋喃環所形成之基團。上述雜環基之中,更佳為形成環之原子數5~20之雜環基,特佳為形成環之原子數5~12之雜環基。又,較佳為二苯並呋喃環、二苯並呋喃基(furanyl)環、咔唑環。 The aromatic heterocyclic group having 5 to 30 atoms in the ring form in the above general formulae (1) to (20) and (51) to (62), for example, a non-condensed aromatic heterocyclic ring and a condensed aromatic heterocyclic ring, More specifically, for example, pyrrolyl, pyrazinyl, pyridyl, decyl, isodecyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophene , quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthryl, anthranyl, phenanthroline, thienyl and by pyridine ring, pyrazine ring, pyrimidine ring, Pyridazine ring, triazine ring, anthracene ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, indazole ring, furan ring, thiophene ring , oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, dibenzofuran ring a group formed by a benzo[c]dibenzofuran ring. Among the above heterocyclic groups, a heterocyclic group having 5 to 20 atoms in the ring is more preferable, and a heterocyclic group having 5 to 12 atoms in the ring is particularly preferable. And, preferably dibenzofuran ring, a dibenzofuran group (furanyl) ring, a carbazole ring.

前述一般式(1)中,未用於與L1鍵結之R1~R10,更佳 為氫原子或烷基等,特佳為氫原子。 In the above general formula (1), R 1 to R 10 which are not bonded to L 1 are used, and a hydrogen atom or an alkyl group is more preferable, and a hydrogen atom is particularly preferable.

R9為形成環之碳數10~30之縮合芳香族烴基時,較佳有 1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基、1-稠四苯基(naphthacenyl)、2-稠四苯基、9-稠四苯基、1-芘基、2-芘基、4-芘基、3-甲基-2-萘基、4-甲基-1-萘基及4-甲基-1-蒽基。 When R 9 is a condensed aromatic hydrocarbon group having 10 to 30 carbon atoms forming a ring, 1-naphthyl group, 2-naphthyl group, 1-fluorenyl group, 2-fluorenyl group, 9-fluorenyl group, and 1-phenanthryl group are preferred. , 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-thyltetraphenyl (naphthacenyl), 2-fused tetraphenyl, 9-fused tetraphenyl, 1-indenyl, 2-indenyl, 4-indenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl and 4-methyl-1-indenyl.

前述一般式(1)中,L1為連結基時,例如有由取代或無取代之形成環之碳數6~30之(a+1)價之芳香族烴基、取代或無取代之形成環之原子數5~10之(a+1)價之雜環基、或取代或無取代之形成環之碳數6~30之芳香族烴基及取代或無取代之形成環之原子數5~10之雜環基所選出之基團,以2~4個鍵結所形成之(a+1)價的基團。 In the above general formula (1), when L 1 is a linking group, for example, a (a+1)-valent aromatic hydrocarbon group having a carbon number of 6 to 30 which is substituted or unsubstituted is formed, and a substituted or unsubstituted ring is formed. a heterocyclic group having an atomic number of 5 to 10 (a+1), or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms and a substituted or unsubstituted atomic number of 5 to 10 The selected group of the heterocyclic group is a (a+1)-valent group formed by 2 to 4 bonding.

形成環之碳數6~30之(a+1)價之芳香族烴基之具體例,例如有使上述形成環之碳數6~30之芳香族烴基所列舉者,形成(a+1)價之基團者。 Specific examples of the aromatic hydrocarbon group having a (a+1)-valent carbon number of 6 to 30 carbon atoms forming the ring include, for example, those having an aromatic hydrocarbon group having 6 to 30 carbon atoms forming the ring, and forming (a+1) valence. The group of people.

又,形成環之原子數5~30之(a+1)價之雜環基之具體例,例如有使上述形成環之原子數5~30之雜環基所列舉者,形成(a+1)價之基團者。 Further, a specific example of the heterocyclic group having a (a+1)-valent atomic number of 5 to 30 atoms in the ring is, for example, a heterocyclic group having 5 to 30 atomic number of the ring formed, and (a+1) is formed. The base of the price.

L1為形成環之碳數6~30之(a+1)價之芳香族烴基時,更佳之芳香族烴基,例如有苯基、聯苯基、萘基、9,9-二甲基茀基。 When L 1 is an aromatic hydrocarbon group having a (a+1)-valent carbon number of 6 to 30 carbon atoms, more preferably an aromatic hydrocarbon group such as a phenyl group, a biphenyl group, a naphthyl group or a 9,9-dimethyl fluorene group. base.

L1為形成環之原子數6~30之(a+1)價之雜環基時,更 佳之雜環基,例如有吡啶基、嘧啶基、二苯並呋喃基、咔唑基。 When L 1 is a (he+1)-valent heterocyclic group having a ring number of atoms of 6 to 30, more preferably a heterocyclic group, for example, a pyridyl group, a pyrimidinyl group, a dibenzofuranyl group or an oxazolyl group.

L1為由取代或無取代之形成環之碳數6~30之芳香族烴基及取代或無取代之形成環之原子數5~10之雜環基所選出之基團,以2~4個鍵結所形成之(a+1)價的基團時,芳香族烴基及雜環基,各自例如有上述者。芳香族烴基,較佳為選自取代或無取代之苯基、取代或無取代之萘基、取代或無取代之菲基、取代或無取代之蒽基、取代或無取代之芘基、取代或無取代之茀基,雜環基較佳為選自取代或無取代之吡啶基、取代或無取代之嘧啶基、取代或無取代之吡嗪基、取代或無取代之噠嗪基、取代或無取代之三嗪基、取代或無取代之二苯並呋喃基、取代或無取代之二苯並噻吩基(thiophenyl)、取代或無取代之咔唑基。(a+1)價更佳為2價。 L 1 is a group selected from a substituted or unsubstituted ring-forming aromatic hydrocarbon group having 6 to 30 carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 10 atoms forming a ring, in the range of 2 to 4 When the (a+1)-valent group formed by bonding is bonded, the aromatic hydrocarbon group and the heterocyclic group are each, for example, as described above. The aromatic hydrocarbon group is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted fluorenyl group, a substituted group. Or an unsubstituted fluorenyl group, preferably a heterocyclic group selected from substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted Or an unsubstituted triazinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group. The (a+1) price is preferably 2.

更佳為以下結構或由以下結構所衍生之(a+1)價的結構。 More preferably, it is a structure of the following structure or (a+1) valence derived from the following structure.

L1為由取代或無取代之形成環之碳數6~30之芳香族烴基及取代或無取代之形成環之原子數5~10之雜環基所選出之基團,以2~4個鍵結所形成之蒽衍生物之較佳結構,例如有以下者。 L 1 is a group selected from a substituted or unsubstituted ring-forming aromatic hydrocarbon group having 6 to 30 carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 10 atoms forming a ring, in the range of 2 to 4 Preferred structures of the anthracene derivative formed by the bonding are, for example, the following.

前述一般式(2)中之R111~R114更佳為氫原子或烷基,特佳為氫原子。 R 111 to R 114 in the above general formula (2) are more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.

前述一般式(3)及(4)中之R121~R124、R125~R128更佳為氫原子或烷基,特佳為氫原子。 R 121 to R 124 and R 125 to R 128 in the above general formulas (3) and (4) are more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.

前述一般式(2)中,R111及R112之取代基為形成前述一般式(4)表示之環時,R117及R118較佳為氫原子,R117及R118之取代基為形成前述一般式(4)表示之環時,R111及R112較佳為氫原子。一般式(2)之R111與R112、或R117與R118為非氫原子,而具有取代基時,因出現立體排除效 果,因此在非晶質薄膜中,與鄰接之分子的距離變大,結果可能造成驅動電壓上昇。因此,一般式(2)之R111及R112之取代基為形成前述一般式(4)表示之環時之R117與R118、及R117及R118之取代基為形成前述一般式(4)表示之環時之R111與R112較佳為氫原子。 In the above general formula (2), when the substituent of R 111 and R 112 is a ring represented by the above general formula (4), R 117 and R 118 are preferably a hydrogen atom, and the substituents of R 117 and R 118 are formed. In the case of the ring represented by the above general formula (4), R 111 and R 112 are preferably a hydrogen atom. R 111 and R 112 of the general formula (2), or R 117 and R 118 are non-hydrogen atoms, and when having a substituent, since the stereoscopic effect is exhibited, the distance from the adjacent molecule in the amorphous film is changed. Large, the result may cause the drive voltage to rise. Therefore, the substituents of R 111 and R 112 in the general formula (2) are those in which R 117 and R 118 and R 117 and R 118 in the ring represented by the above general formula (4) are formed to form the above general formula ( 4) R 111 and R 112 in the ring represented by a ring are preferably a hydrogen atom.

前述一般式(11)中,Ar1特佳為苯基、萘基、菲基、9,9-二甲基茀基、聯苯基。 In the above general formula (11), Ar 1 is particularly preferably a phenyl group, a naphthyl group, a phenanthryl group, a 9,9-dimethylfluorenyl group or a biphenyl group.

Ra特佳為氫原子、芳基、或雜環基。 Ra is preferably a hydrogen atom, an aryl group or a heterocyclic group.

本發明中,「形成環之碳」係指構成飽和環、不飽和環、或芳香環的碳原子。「形成環之原子」係指構成雜環(包括飽和環、不飽和環、及芳香環)之碳原子及雜原子。 In the present invention, the "carbon forming a ring" means a carbon atom constituting a saturated ring, an unsaturated ring or an aromatic ring. The "atom forming a ring" means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).

本發明中,氫原子係指中性子數不同的同位素,即包含氕(protium)、氘(deuterium)、氚(tritium)。 In the present invention, a hydrogen atom means an isotope having a different number of neutrals, that is, a protium, a deuterium, and a tritium.

又,「取代或無取代之」情況時之取代基,例如有如上述之芳香族烴基、雜環基、烷基(直鏈或支鏈之烷基、環烷基、鹵烷基)、烷氧基、芳氧基、芳烷基、鹵烷氧基、烷基甲矽烷基、二烷基芳基甲矽烷基、烷基二芳基甲矽烷基、三芳基甲矽烷基、鹵素原子、氰基、羥基、硝基及羧基。其他亦有烯基、炔基。 Further, the substituent in the case of "substituted or unsubstituted" may, for example, be an aromatic hydrocarbon group, a heterocyclic group, an alkyl group (linear or branched alkyl group, cycloalkyl group, haloalkyl group) or alkoxy group as described above. Alkyl, aryloxy, aralkyl, haloalkoxy, alkylcarboxyalkyl, dialkylarylcarboxyalkyl, alkyldiarylcarbenyl, triarylcarbenyl, halogen atom, cyano , hydroxyl, nitro and carboxyl groups. Others also have alkenyl groups and alkynyl groups.

在此所列舉之取代基中,較佳為芳香族烴基、雜環基、烷基、鹵素原子、烷基甲矽烷基、芳基甲矽烷基、氰基,此外,各取代基之說明中,更佳為較佳之具體的取代基。 The substituents exemplified herein are preferably an aromatic hydrocarbon group, a heterocyclic group, an alkyl group, a halogen atom, an alkylcarbenyl group, an arylcarbinyl group or a cyano group. Further, in the description of each substituent, More preferred are preferred specific substituents.

「取代或無取代之」時之「無取代」係指未被前述取 代基取代,鍵結有氫原子者。 "Unsubstituted" when "replaced or unsubstituted" means not taken from the foregoing The substituent is substituted and the hydrogen atom is bonded to it.

又,本說明書中,「取代或無取代之碳數a~b之XX基」的表達中之「碳數a~b」係表示XX基為無取代時的碳數,不包含XX基被取代時之取代基的碳數。 In the present specification, the "carbon number a to b" in the expression "substituted or unsubstituted carbon number a to b XX group" means that the XX group is an unsubstituted carbon number, and the XX group is not substituted. The carbon number of the substituent.

以下所說明之化合物或其部分結構中,對於「取代或無取代之」的情形,也與前述同樣。 In the case of the compound described below or a partial structure thereof, the case of "substituted or unsubstituted" is also the same as described above.

以下表示以一般式(1)表示之蒽衍生物之具體例,但是本發明不限於此等例示化合物。 Specific examples of the anthracene derivative represented by the general formula (1) are shown below, but the present invention is not limited to the above-exemplified compounds.

又,以前述一般式(1)所表示之蒽衍生物之具体例,例如有下述一般式(1X)表示。 Moreover, the specific example of the anthracene derivative represented by the above general formula (1) is represented, for example, by the following general formula (1X).

前述一般式(1X)中之A及B係下表所示。 A and B in the above general formula (1X) are shown in the following table.

上述表中之各欄所示之A及B之構造所具有之鍵結之前端所示之下述符號(參照下述(10X)),分別表示對蒽環之鍵結位置。 The following symbols (see (10X) below) shown at the front end of the bond of the structures A and B shown in the respective columns in the above table indicate the bonding positions of the ring.

(10X) * (10X)

因此,例如具有上述表之左列之最上段欄所示之A及B之結構的蒽衍生物係以下述式表示。 Therefore, for example, an anthracene derivative having the structures of A and B shown in the uppermost column of the left column of the above table is represented by the following formula.

其他前述一般式(1X)所表示之蒽衍生物,對於下述表中記載之A及B的結構,與前述同樣適用。 The anthracene derivatives represented by the above general formula (1X) are similar to those described above for the structures of A and B described in the following tables.

.摻雜劑材料 . Dopant material

本實施形態之有機EL元件中,發光層含有前述一般式(1)表示之蒽衍生物及下述一般式(21)表示之衍生物。本實施形態之有機EL元件係以下述一般式(21)表示之衍生物作為摻雜劑材料使用。 In the organic EL device of the present embodiment, the light-emitting layer contains the anthracene derivative represented by the above formula (1) and is represented by the following general formula (21). derivative. The organic EL device of the present embodiment is represented by the following general formula (21). The derivative is used as a dopant material.

前述一般式(21)中,R20~R29各自表示為氫原子、鹵素原子、氰基、取代或無取代之碳數1~20之烷基、取代或無取代之甲矽烷基(silyl)、或取代或無取代之形成環之碳數6~30之芳香族烴基。 In the above general formula (21), R 20 to R 29 are each represented by a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted meyl group (silyl). Or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms forming a ring.

前述一般式(21)中之Ar21~Ar24各自表示取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基。 Ar 21 to Ar 24 in the above general formula (21) each represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms forming a ring, or a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms. base.

前述一般式(21)中之Ar21~Ar24具有烷基作為取代基時,各自至少具有2個以上之烷基。 When Ar 21 to Ar 24 in the above general formula (21) have an alkyl group as a substituent, each has at least two or more alkyl groups.

上述一般式(21)中之鹵素原子、烷基、芳香族烴基、雜環基,例如有上述一般式(1)~(20),(51)~(62)所說明的基團。 The halogen atom, the alkyl group, the aromatic hydrocarbon group, and the heterocyclic group in the above general formula (21) are, for example, those described in the above general formulas (1) to (20) and (51) to (62).

取代或無取代之甲矽烷基,例如有取代或無取代之碳數1~10之直鏈狀、支鏈狀或環狀之烷基甲矽烷基、及取代或無取代之碳數6~30之芳基甲矽烷基。 A substituted or unsubstituted methylidene group, for example, a substituted or unsubstituted linear, branched or cyclic alkylcarboxyalkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted carbon number of 6 to 30 Arylcarbylalkyl.

碳數1~10之直鏈狀、支鏈狀或環狀之烷基甲矽烷基,例如有三甲基甲矽烷基、三乙基甲矽烷基、三丁基甲矽烷基、二甲基乙基甲矽烷基、二甲基異丙基甲矽烷基、二甲基丙基甲矽烷基、二甲基丁基甲矽烷基、二甲基第三丁基甲矽烷基、二乙基異丙基甲矽烷基等。 a linear, branched or cyclic alkylcarboxyalkyl group having 1 to 10 carbon atoms, for example, trimethylmethanyl, triethylmethane, tributylmethylalkyl, dimethylethylformane Base, dimethylisopropylmethanyl, dimethylpropylmethyl decyl, dimethyl butyl decyl, dimethyl tert-butyl decyl, diethyl isopropyl decyl, and the like.

碳數6~30之芳基甲矽烷基,例如有苯基二甲基甲矽烷基、二苯基甲基甲矽烷基、二苯基-t-丁基甲矽烷基、三苯基甲矽烷基。 The arylcarbenyl group having 6 to 30 carbon atoms may, for example, be phenyldimethylformamidinyl, diphenylmethylformamidinyl, diphenyl-t-butylformamyl or triphenylcarbenyl.

上述一般式(21)中,R20~R29較佳為氫原子。 In the above general formula (21), R 20 to R 29 are preferably a hydrogen atom.

又,一般式(21)中,Ar21~Ar24各自具有2個以上之取代基較佳。 Further, in the general formula (21), it is preferred that each of Ar 21 to Ar 24 has two or more substituents.

上述一般式(21)中,Ar21~Ar24之中,至少1個為以下述式(42)表示之雜環基較佳。 In the above general formula (21), at least one of Ar 21 to Ar 24 is preferably a heterocyclic group represented by the following formula (42).

[前述一般式(42)中,R211~R217各自表示氫原子、鹵素原子、氰基、取代或無取代之碳數1~20之烷基、取代或無取代之碳數2~20之烯基、取代或無取代之碳數2~20之炔基、取代或無取代甲矽烷基、取代或無取代之形成環之碳數6~30之芳香族烴基或取代或無取代之形成環之原子數5~30之雜環基。 [In the above general formula (42), R 211 to R 217 each represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted carbon number of 2 to 20; Alkenyl, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted metaalkyl group, substituted or unsubstituted ring-forming aromatic hydrocarbon group having 6 to 30 carbon atoms or substituted or unsubstituted ring forming ring A heterocyclic group having 5 to 30 atoms.

又,R211與R212、R212與R213、R213與R214、R215與R216、及R216與R217彼此鍵結可形成飽和或不飽和的環,此等之環可被取代。 Further, R 211 and R 212 , R 212 and R 213 , R 213 and R 214 , R 215 and R 216 , and R 216 and R 217 are bonded to each other to form a saturated or unsaturated ring, and the rings may be Replace.

X21係選自氧原子或硫原子之任一。 X 21 is selected from any of an oxygen atom or a sulfur atom.

y21係與前述一般式(21)之氮原子鍵結的單鍵。 Y 21 is a single bond bonded to the nitrogen atom of the above general formula (21).

上述一般式(21)更佳為以下述一般式(22)表示者。 The above general formula (21) is more preferably expressed by the following general formula (22).

前述一般式(22)中,A1~A4各自獨立為選自由氫原子、鹵素原子、取代或無取代之碳數1~20之烷基、取代或無取代之碳數1~20之烷氧基、取代或無取代之形成環之碳數6~30之芳氧基、取代或無取代之碳數7~30之芳烷基、取代或無取代之胺基、取代或無取代之甲矽烷基、取代或無取代之形成環之碳數6~30之芳香族烴基、及取代或無取代之形成環之原子數5~30之雜環基所成之第一群。 In the above general formula (22), A 1 to A 4 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. An oxy, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted group A A first group of a decyl group, a substituted or unsubstituted ring-forming aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

p,q,r及s各自獨立為0~3之整數,p,q,r及s各自為2以上時,A1~A4係相同或相異。 p, q, r and s are each independently an integer of 0 to 3, and when p, q, r and s are each 2 or more, A 1 to A 4 are the same or different.

前述一般式(22)中,A5~A12各自獨立為選自鹵素原子、取代或無取代之碳數1~20之烷基、取代或無取代之碳數1~20之烷氧基、取代或無取代之形成環之碳數6~30 之芳氧基、取代或無取代之碳數7~30之芳烷基、取代或無取代之胺基、取代或無取代之甲矽烷基、取代或無取代之形成環之碳數6~30之芳香族烴基、及取代或無取代之形成環之原子數5~30之雜環基。 In the above general formula (22), A 5 to A 12 are each independently a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted methyro group, The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms and the substituted or unsubstituted heterocyclic group having 5 to 30 atoms forming a ring.

又,A5與A6、A7與A8、A9與A10、A11與A12可互相連結形成飽和或不飽和的環。 Further, A 5 and A 6 , A 7 and A 8 , A 9 and A 10 , and A 11 and A 12 may be bonded to each other to form a saturated or unsaturated ring.

前述一般式(22)中,A5~A12各自獨立為取代或無取代之碳數1~20之烷基更佳。 In the above general formula (22), each of A 5 to A 12 is preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

以下表示前述一般式(21)及前述一般式(22)表示之衍生物之具體例,但是本發明不限於此等例示化合物。 The following shows the general formula (21) and the above general formula (22). Specific examples of the derivative, but the invention is not limited to the exemplified compounds.

本實施形態中,摻雜劑材料在發光層中之含量,無特別限定,可配合目的適當選擇,例如較佳為0.1質量%以上、70質量%以下,更佳為1質量%以上、30質量%以下。摻雜劑材料之含量在0.1質量%以上時,可得到充分的發光,在70質量%以下時,可避免濃度消光。 In the present embodiment, the content of the dopant material in the light-emitting layer is not particularly limited, and may be appropriately selected in accordance with the purpose, and is, for example, preferably 0.1% by mass or more and 70% by mass or less, more preferably 1% by mass or more and 30% by mass. %the following. When the content of the dopant material is 0.1% by mass or more, sufficient light emission can be obtained, and when it is 70% by mass or less, concentration extinction can be avoided.

本實施形態中,發光層所含之摻雜劑材料,其發光色無特別限定,但是以顯示主波峰波長為480nm以下之藍色發光之螢光發光性之摻雜劑材料為佳。主波峰波長係指在濃度10-6莫耳/升以上、10-5莫耳/升以下之甲苯溶液中所測定之發光光譜中發光強度成為最大之發光光譜之波峰波長。 In the present embodiment, the dopant color of the dopant material contained in the light-emitting layer is not particularly limited, but a dopant material having a fluorescent property of blue light emission having a main peak wavelength of 480 nm or less is preferable. The main peak wavelength refers to the peak wavelength of the luminescence spectrum in which the luminescence intensity is maximum in the luminescence spectrum measured in a toluene solution having a concentration of 10 -6 mol/liter or more and 10 -5 mol/liter or less.

將這種主波峰波長之摻雜劑材料摻雜於前述一般式(1)表示之主體材料中,構成發光層時,有機EL元件變成高效率且長壽命。 When the dopant material of the main peak wavelength is doped into the host material represented by the above general formula (1) to form a light-emitting layer, the organic EL element becomes highly efficient and has a long life.

.主體材料及摻雜劑材料之組合 . Combination of host material and dopant material

本實施形態中,主體材料使用前述一般式(1)之Z1為前述一般式(5)~(10)表示之蒽衍生物較佳,特佳為Z1使用前述一般式(8)~(10)表示之萘並苯並呋喃。以萘並苯並呋喃取代蒽時,因萘並苯並呋喃之平面性,因此推測提高發光層中之分子間之堆疊(packing),因而電荷移動度變高。此時,電荷由發光層中漏出,可能使效率及壽命降低。因此,使用具有電子或電洞捕捉(trap)性,且具有縮合環結構之摻雜劑,可將載體(carrier)關閉於在發光層內,可達成高效率且長壽命。將具有電子捕捉性,且具有縮合環結構之一般式(21)表示之化合物(二胺基衍生物)作為摻雜劑材料使用,可將電荷關閉於發光層內,可達成高效率化及長壽命化。 In the present embodiment, the host material is preferably an anthracene derivative represented by the above general formulas (5) to (10) using Z 1 of the above general formula (1), and particularly preferably Z 1 is the above general formula (8) to ((). 10) represents naphthobenzofuran. When ruthenium is substituted with naphthobenzofuran, since the planarity of naphthobenzofuran is increased, it is presumed that the packing between molecules in the light-emitting layer is increased, and thus the degree of charge mobility becomes high. At this time, electric charges are leaked from the light-emitting layer, which may lower efficiency and life. Therefore, by using a dopant having electron or hole trapping property and having a condensed ring structure, the carrier can be closed in the light-emitting layer, and high efficiency and long life can be achieved. a compound represented by the general formula (21) having an electron trapping property and having a condensed ring structure (diamine group) As a dopant material, the derivative can be used to close the electric charge in the light-emitting layer, thereby achieving high efficiency and long life.

(電洞注入.輸送層) (hole injection. conveying layer)

電洞注入.輸送層係幫助電洞注入發光層,輸送至發光區域的層,可使用電洞移動度大,且游離能(ionization energy)小的化合物。 Hole injection. The transport layer helps the hole to be injected into the light-emitting layer and is transported to the layer of the light-emitting region, and a compound having a large hole mobility and a small ionization energy can be used.

形成電洞注入.輸送層的材料,較佳為更低的電場強度,將電洞輸送至發光層的材料,較佳為例如使用芳香族胺化合物。 Forming a hole injection. The material of the transport layer, preferably a lower electric field strength, is preferably a material for transporting the holes to the light-emitting layer, for example, an aromatic amine compound.

(電子注入.輸送層) (electron injection. transport layer)

電子注入.輸送層係幫助電子注入發光層,輸送至發光區域的層,可使用電子移動度大的化合物。 Electron injection. The transport layer is a layer that allows electrons to be injected into the light-emitting layer and transported to the light-emitting region, and a compound having a large electron mobility can be used.

電子注入.輸送層用的化合物,例如使用分子內具有1個以上之雜原子之芳香族雜環化合物較佳,特佳為含氮環衍生物。含氮環衍生物較佳為具有含氮6員環或5員環骨架之雜環化合物。 Electron injection. The compound for the transport layer is preferably an aromatic heterocyclic compound having one or more hetero atoms in the molecule, and particularly preferably a nitrogen-containing ring derivative. The nitrogen-containing cyclic derivative is preferably a heterocyclic compound having a nitrogen-containing 6-membered ring or a 5-membered ring skeleton.

本發明之有機EL元件中,發光層以外之有機層除上述例示的化合物外,可自以往有機EL元件中使用之材料中選擇任意化合物使用。 In the organic EL device of the present invention, the organic layer other than the light-emitting layer may be selected from any of the materials used in the conventional organic EL device in addition to the compounds exemplified above.

(基板) (substrate)

本實施形態之有機EL元件係製作於透光性之基板上。此透光性基板係支持構成有機EL元件之陽極、有機層、陰極等的基板,較佳為400nm以上700nm以下之可見光區域之光線透過率為50%以上,且平滑的基板。 The organic EL device of the present embodiment is fabricated on a light-transmissive substrate. The light-transmitting substrate supports a substrate constituting an anode, an organic layer, a cathode, or the like of the organic EL element, and preferably has a light transmittance of 50% or more in a visible light region of 400 nm or more and 700 nm or less, and is a smooth substrate.

透光性基板,例如有玻璃板、聚合物板等。 The light-transmitting substrate is, for example, a glass plate, a polymer plate or the like.

玻璃板例如有特別是鈉鈣玻璃、含有鋇.鍶之玻璃、鉛玻璃、鋁矽酸玻璃、硼矽酸玻璃、鋇硼矽酸玻璃、以石英作為原料使用所成者。 The glass plate is, for example, especially soda lime glass, containing bismuth. Glass of bismuth, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz are used as raw materials.

聚合物板例如有聚碳酸酯、丙烯酸、聚對苯二甲酸乙二酯、聚硫醚、聚碸等作為原料使用所成者。 The polymer sheet is, for example, polycarbonate, acrylic acid, polyethylene terephthalate, polythioether, polyfluorene or the like as a raw material.

(陽極及陰極) (anode and cathode)

有機EL元件之陽極係擔任將電洞注入發光層的功能者,而以具有4.5eV以上之功函數者較具效果。 The anode of the organic EL element serves as a function of injecting a hole into the light-emitting layer, and is more effective in having a work function of 4.5 eV or more.

陽極材料之具體例有氧化銦錫合金(ITO)、氧化錫 (NESA)、氧化銦鋅氧化物、金、銀、鉑、銅等。 Specific examples of the anode material are indium tin oxide alloy (ITO), tin oxide. (NESA), indium zinc oxide, gold, silver, platinum, copper, and the like.

由陽極側取出來自發光層之發光時,較佳為使陽極之可見光區域之光線透過率大於10%者。另外,陽極之薄片電阻較佳為數百Ω/□(Ω/sq)以下。陽極之膜厚係依材料而異,但是通常選擇10nm以上、1μm以下,較佳為10nm以上200nm以下的範圍。 When the light emitted from the light-emitting layer is taken out from the anode side, it is preferred that the light transmittance of the visible light region of the anode is greater than 10%. Further, the sheet resistance of the anode is preferably several hundred Ω/□ (Ω/sq) or less. The film thickness of the anode varies depending on the material, but is usually 10 nm or more and 1 μm or less, preferably 10 nm or more and 200 nm or less.

陰極為了將電子注入發光層,以功函數由小的材料為佳。 In order to inject electrons into the light-emitting layer, the cathode preferably has a work function of a small material.

陰極材料無特別限定,具體而言可使用銦、鋁、鎂、鎂-銦合金、鎂-鋁合金、鋁-鋰合金、鋁-鈧-鋰合金、鎂-銀合金等。 The cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-niobium-lithium alloy, magnesium-silver alloy, or the like can be used.

陰極也與陽極同樣,可藉由以蒸鍍法等之方法,例如可在電子輸送層或電子注入層上形成薄膜。另外,也可採用由陰極側取出來自發光層之發光的形態。由陰極側取出來自發光層之發光時,陰極之可見光區域之光之透過率較佳為大於10%。 Similarly to the anode, the cathode can be formed into a thin film on the electron transport layer or the electron injection layer by a vapor deposition method or the like. Further, a form in which light emitted from the light-emitting layer is taken out from the cathode side may be employed. When the light emitted from the light-emitting layer is taken out from the cathode side, the light transmittance in the visible light region of the cathode is preferably more than 10%.

陰極之薄片電阻較佳為數百Ω/□以下。 The sheet resistance of the cathode is preferably several hundred Ω/□ or less.

陰極之膜厚係依材料而異,但是通常為10nm以上、1μm以下,較佳為選擇50nm以上、200nm以下之範圍。 The film thickness of the cathode varies depending on the material, but is usually 10 nm or more and 1 μm or less, and preferably 50 nm or more and 200 nm or less.

(有機EL元件之各層的形成方法) (Method of Forming Each Layer of Organic EL Element)

本實施形態之有機EL元件之各層之形成方法並未特別限定。可使用以往周知之真空蒸鍍法、旋轉塗佈法等之形成方法。本實施形態之有機EL元件所使用之有機層係 可藉由真空蒸鍍法、分子射線蒸鍍法(MBE法、MBE;Molecular Beam Epitaxy)或溶解於溶劑之溶液之浸塗法、旋轉塗佈法、鑄膜法(casting)、棒塗法、輥塗佈法等之塗佈法之周知方法而形成。 The method for forming each layer of the organic EL device of the present embodiment is not particularly limited. A conventionally known method of forming a vacuum vapor deposition method, a spin coating method, or the like can be used. The organic layer used in the organic EL device of the present embodiment The method may be a vacuum deposition method, a molecular beam evaporation method (MBE method, MBE; Molecular Beam Epitaxy) or a dip coating method in which a solution dissolved in a solvent, a spin coating method, a casting method, a bar coating method, or the like. It is formed by a well-known method of the coating method, such as a roll coating method.

(有機EL元件之各層之膜厚) (Thickness of each layer of the organic EL element)

發光層之膜厚,較佳為5nm以上、50nm以下,更佳為7nm以上、50nm以下,最佳為10nm以上、50nm以下。發光層之膜厚為5nm以上,變得容易形成發光層,容易調整色度。發光層之膜厚為50nm以下,可抑制驅動電壓之上昇。 The film thickness of the light-emitting layer is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and most preferably 10 nm or more and 50 nm or less. The film thickness of the light-emitting layer is 5 nm or more, and it becomes easy to form a light-emitting layer, and it is easy to adjust the chromaticity. The film thickness of the light-emitting layer is 50 nm or less, and the increase in the driving voltage can be suppressed.

其他各有機層之膜厚並未特別限制,通常為數nm~1μm之範圍較佳。在這種膜厚範圍時,可防止因膜厚過薄所造成之針孔等缺陷,也可抑制因膜厚過厚造成驅動電壓上昇,可防止效率惡化。 The film thickness of each of the other organic layers is not particularly limited, but is usually in the range of several nm to 1 μm. In such a film thickness range, defects such as pinholes caused by an excessively thin film thickness can be prevented, and an increase in driving voltage due to an excessive thickness can be suppressed, and deterioration in efficiency can be prevented.

[第2實施形態] [Second Embodiment]

其次說明2實施形態之有機EL元件。 Next, an organic EL device of the second embodiment will be described.

本實施形態之有機EL元件,其中發光層所含有之化合物為以前述一般式(1)表示之蒽衍生物及下述一般式(41)表示之芘衍生物,此點與第1實施形態之有機EL元件不同。其他點方面,第2實施形態之有機EL元件係與第1實施形態之有機EL元件相同。又,第2實施形態中,未特別提及之材料或化合物,可使用與第1實施形態說明者 同樣的材料或化合物。第2實施形態之有機EL元件中,發光層所含有之蒽衍生物等之較佳的化合物或其取代基等也與第1實施形態之說明相同。又,第2實施形態之有機EL元件之概略構成也與圖1所示者相同。 In the organic EL device of the present embodiment, the compound contained in the light-emitting layer is an anthracene derivative represented by the above formula (1) and an anthracene derivative represented by the following general formula (41), and the first embodiment The organic EL elements are different. In other respects, the organic EL device of the second embodiment is the same as the organic EL device of the first embodiment. Further, in the second embodiment, materials or compounds not specifically mentioned may be used as described in the first embodiment. The same material or compound. In the organic EL device of the second embodiment, a preferred compound such as an anthracene derivative contained in the light-emitting layer or a substituent thereof is also the same as that described in the first embodiment. Further, the schematic configuration of the organic EL element of the second embodiment is also the same as that shown in FIG. 1.

(發光層) (lighting layer)

本實施形態之有機EL元件中,發光層含有前述一般式(1)表示之蒽衍生物、及下述一般式(41)表示之芘衍生物。 In the organic EL device of the present embodiment, the light-emitting layer contains the anthracene derivative represented by the above formula (1) and the anthracene derivative represented by the following general formula (41).

.摻雜劑材料 . Dopant material

本實施形態之有機EL元件中,以下述一般式(41)表示之芘衍生物可作為摻雜劑材料使用,以前述一般式(1)表示之蒽衍生物可作為主體材料使用。 In the organic EL device of the present embodiment, the anthracene derivative represented by the following general formula (41) can be used as a dopant material, and the anthracene derivative represented by the above general formula (1) can be used as a host material.

前述一般式(41)中,R21~R28各自獨立為氫原子、鹵素原子、氰基、取代或無取代之碳數1~20之烷基、取代或無取代之甲矽烷基(silyl)、或取代或無取代之形成環之碳數6~30之芳香族烴基,前述一般式(41)中之Ar21~Ar24各自表示取代或無取 代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基。 In the above general formula (41), R 21 to R 28 are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted meyl group (silyl). Or a substituted or unsubstituted aromatic hydrocarbon group having a carbon number of 6 to 30, wherein Ar 21 to Ar 24 in the above general formula (41) each represent a substituted or unsubstituted aromatic ring having a carbon number of 6 to 30. a hydrocarbon group, or a substituted or unsubstituted heterocyclic group having 5 to 30 atomic atoms forming a ring.

但是前述一般式(41)中之Ar21~Ar24之中,至少1個為以下述式(42)表示之雜環基。 However, at least one of Ar 21 to Ar 24 in the above general formula (41) is a heterocyclic group represented by the following formula (42).

前述一般式(42)中,R211~R217各自表示氫原子、鹵素原子、氰基、取代或無取代之碳數1~20之烷基、取代或無取代之碳數2~20之烯基、取代或無取代之碳數2~20之炔基、取代或無取代甲矽烷基、取代或無取代之形成環之碳數6~30之芳香族烴基或取代或無取代之形成環之原子數5~30之雜環基。 In the above general formula (42), R 211 to R 217 each represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted carbon number of 2 to 20 carbon atoms. a substituted, unsubstituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted metaalkyl group, a substituted or unsubstituted ring-forming aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming ring. A heterocyclic group having 5 to 30 atoms.

又,前述一般式(42)中,R211與R212、R212與R213、R213與R214、R215與R216、及R216與R217彼此鍵結可形成飽和或不飽和的環,此等之環可被取代。 Further, in the above general formula (42), R 211 and R 212 , R 212 and R 213 , R 213 and R 214 , R 215 and R 216 , and R 216 and R 217 are bonded to each other to form a saturated or unsaturated group. Rings, such rings can be replaced.

前述一般式(42)中,X21係選自氧原子或硫原子之任一。 In the above general formula (42), X 21 is selected from any one of an oxygen atom or a sulfur atom.

前述一般式(42)中,y21係與前述一般式(41)之氮原子鍵結的單鍵。 In the above general formula (42), y 21 is a single bond bonded to the nitrogen atom of the above general formula (41).

前述一般式(41)及(42)中之鹵素原子、芳香族烴基、雜環基、烷基、烷氧基、芳氧基、芳硫基、芳基胺基,例如有以前述一般式(1)~(20),(51)~(62)所說明的基團。 The halogen atom, aromatic hydrocarbon group, heterocyclic group, alkyl group, alkoxy group, aryloxy group, arylthio group or arylamine group in the above general formulas (41) and (42), for example, have the above general formula ( 1) ~(20), (51)~(62) The groups described.

前述一般式(41)及(42)中之甲矽烷基,例如無取代之甲矽烷基外,例如有碳數1~30之烷基甲矽烷基及碳數6~60之芳基甲矽烷基。 The methylidene group in the above general formulas (41) and (42), for example, an unsubstituted methyroalkyl group, for example, an alkylmercaptoalkyl group having 1 to 30 carbon atoms and an arylmethylalkyl group having 6 to 60 carbon atoms. .

碳數1~30之烷基甲矽烷基,例如具有以上述碳數1~20之烷基所例示之烷基的三烷基甲矽烷基,具體而言,例如有三甲基甲矽烷基、三乙基甲矽烷基、三-n-丁基甲矽烷基、三-n-辛基甲矽烷基、三異丁基甲矽烷基、二甲基乙基甲矽烷基、二甲基異丙基甲矽烷基、二甲基-n-丙基甲矽烷基、二甲基-n-丁基甲矽烷基、二甲基-t-丁基甲矽烷基、二乙基異丙基甲矽烷基、乙烯基二甲基甲矽烷基、丙基二甲基甲矽烷基、三異丙基甲矽烷基等。3個烷基各自可相同或相異。 The alkylmercaptoalkyl group having 1 to 30 carbon atoms, for example, a trialkylcarbenyl group having an alkyl group exemplified by the above alkyl group having 1 to 20 carbon atoms, specifically, for example, trimethylcarbinyl group, or Ethylmethylation, tri-n-butylcarboxyalkyl, tri-n-octylcarboxyalkyl, triisobutylcarboxyalkyl, dimethylethylformamidinyl, dimethylisopropylformamidinyl, Methyl-n-propylcarboxyalkyl, dimethyl-n-butylcarboxyalkyl, dimethyl-t-butylformamidinyl, diethylisopropylformamidinyl, vinyl dimethylformamidinyl, Propyl dimethylformamyl, triisopropylcarbylalkyl and the like. Each of the three alkyl groups may be the same or different.

形成環之碳數6~60之芳基甲矽烷基,例如有芳基甲矽烷基、烷基芳基甲矽烷基、二烷基芳基甲矽烷基、二芳基甲矽烷基、烷基二芳基甲矽烷基、三芳基甲矽烷基。複數之芳基彼此、或烷基彼此可相同或相異。 An arylcarbenyl group having a carbon number of 6 to 60 formed by a ring, for example, an arylcarbenyl group, an alkylarylcarbenyl group, a dialkylarylcarbenyl group, a diarylmethylalkyl group, an alkyl group Arylcarboxyalkyl, triarylcarbinyl. The plural aryl groups may be the same or different from each other or the alkyl groups.

二烷基芳基甲矽烷基,例如具有2個之以上述碳數1~20之烷基所例示之烷基,且具有1個之上述形成環之碳數6~30之芳香族烴基的二烷基芳基甲矽烷基。二烷基芳基甲矽烷基之碳數,較佳為8~30。2個烷基各自可相同或相異。 a dialkyl aryl methantylene group, for example, an alkyl group having two alkyl groups having the above carbon number of 1 to 20, and having one of the above-mentioned aromatic hydrocarbon groups having 6 to 30 carbon atoms forming a ring Alkylarylcarboxyalkyl. The carbon number of the dialkylarylmethanyl group is preferably from 8 to 30. The two alkyl groups may be the same or different.

烷基二芳基甲矽烷基,例如有具有1個之以上述碳數1~20之烷基所例示之烷基,且具有2個之以上述形成環之碳數6~30之芳香族烴基之烷基二芳基甲矽烷基。烷基二芳基甲矽烷基之碳數,較佳為13~30。2個芳基各自可相同或相異。 The alkyl diarylcarbinyl group has, for example, an alkyl group having one alkyl group having 1 to 20 carbon atoms as described above, and having two aromatic hydrocarbon groups having 6 to 30 carbon atoms forming the ring. Alkyl diarylcarbenyl. The carbon number of the alkyldiarylcarbenyl group is preferably from 13 to 30. The two aryl groups may each be the same or different.

三芳基甲矽烷基,例如具有3個之上述形成環之碳數6~30之芳香族烴基之三芳基甲矽烷基。三芳基甲矽烷基之碳數,較佳為18~30。3個芳基各自可相同或相異。 The triarylcarbinyl group is, for example, a triarylcarbenyl group having three of the above-mentioned aromatic hydrocarbon groups having 6 to 30 carbon atoms forming a ring. The carbon number of the triarylcarbenyl group is preferably from 18 to 30. The three aryl groups may each be the same or different.

這種芳基甲矽烷基,例如有苯基二甲基甲矽烷基、二苯基甲基甲矽烷基、二苯基-t-丁基甲矽烷基、三苯基甲矽烷基。 Such an arylcarbenyl group is, for example, phenyldimethylformamidinyl, diphenylmethylformamidine, diphenyl-t-butylformamyl, or triphenylcarbenyl.

前述一般式(42)中之碳數2~20之烯基,可為直鏈、支鏈或環狀之任一,例如有乙烯基、丙烯基、丁烯基、油基、二十碳五烯基(icosapentaenyl)、二十二碳六烯基(docosahexenyl)、苯乙烯基、2,2-二苯基乙烯基、1,2,2-三苯基乙烯基、2-苯基-2-丙烯基等。上述烯基中,較佳為乙烯基。 The alkenyl group having 2 to 20 carbon atoms in the above general formula (42) may be any of a straight chain, a branched chain or a cyclic group, for example, a vinyl group, a propenyl group, a butenyl group, an oil group, and a 20 carbon five. Alkenyl (icosapentaenyl), docosahexenyl, styryl, 2,2-diphenylvinyl, 1,2,2-triphenylvinyl, 2-phenyl-2- Propylene and the like. Among the above alkenyl groups, a vinyl group is preferred.

前述一般式(42)中之碳數2~20之炔基,可為直鏈、支鏈或環狀中任一,例如有乙炔基、丙炔基、2-苯基乙炔基等。上述炔基中,較佳為乙炔基。 The alkynyl group having 2 to 20 carbon atoms in the above general formula (42) may be any of a straight chain, a branched chain or a cyclic group, and examples thereof include an ethynyl group, a propynyl group, a 2-phenylethynyl group and the like. Among the above alkynyl groups, an ethynyl group is preferred.

前述一般式(42)中,R211與R212、R212與R213、R213與R214、R215與R216、及R216與R217彼此鍵結可形成飽和或不飽和的環,例如有環丁烷、環戊烷、環己烷、金剛烷、降莰烷等之形成環之碳數4~12之環烷烴、環丁烯、 環戊烯、環己烯、環庚烯、環辛烯等之形成環之碳數4~12之環烯烴、環己二烯、環庚二烯、環辛二烯等之形成環之碳數6~12之環烷二烯、苯、萘、菲、蒽、芘、、苊烯等之形成環之碳數6~50之芳香族環等。又,取代基例如有與前述例相同者。 In the above general formula (42), R 211 and R 212 , R 212 and R 213 , R 213 and R 214 , R 215 and R 216 , and R 216 and R 217 are bonded to each other to form a saturated or unsaturated ring. For example, a cycloalkane, a cyclopentane, a cyclopentene, a cyclohexene, a cycloheptene having a ring number of 4 to 12, such as cyclobutane, cyclopentane, cyclohexane, adamantane or norbornane. a cycloalkane, a benzene, a naphthalene having a carbon number of 4 to 12, such as a cyclic olefin having 4 to 12 carbon atoms, a cyclohexadiene, a cycloheptadiene or a cyclooctadiene formed by a cyclooctene or the like. , Philippine, 蒽, 芘, An aromatic ring having a carbon number of 6 to 50 which forms a ring such as a terpene. Further, the substituent is, for example, the same as the above examples.

前述一般式(41)中,Ar21及Ar23較佳為前述一般式(42)表示之雜環基。 In the above general formula (41), Ar 21 and Ar 23 are preferably a heterocyclic group represented by the above general formula (42).

前述一般式(41)中,R21~R28較佳為氫原子。 In the above general formula (41), R 21 to R 28 are preferably a hydrogen atom.

前述一般式(41)之R22及R26為取代或無取代之碳數1~20之烷基、或取代或無取代之碳數3~30之烷基甲矽烷基,R21、R23、R24、R25、R27、R28更佳為氫原子。 R 22 and R 26 in the above general formula (41) are a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkylcarbenyl group having 3 to 30 carbon atoms, R 21 and R 23 . R 24 , R 25 , R 27 and R 28 are more preferably a hydrogen atom.

又,前述一般式(42)之X21較佳為氧原子。 Further, X 21 of the above general formula (42) is preferably an oxygen atom.

特佳為前述一般式(41)中之Ar21~Ar24為以前述一般式(42)表示,X21為氧原子。 Particularly preferably, Ar 21 to Ar 24 in the above general formula (41) are represented by the above general formula (42), and X 21 is an oxygen atom.

前述一般式(41)表示之化合物之較佳形態,例如有以下述一般式(43)表示者。 A preferred embodiment of the compound represented by the above formula (41) is, for example, represented by the following general formula (43).

前述一般式(43)中,R21~R28各自表示氫原子、鹵素原子、氰基取代或無取代之碳數1~20之烷基、取代或無取代之甲矽烷基、或取代或無取代之形成環之碳數6~30之芳香族烴基,R218~R241各自表示氫原子、鹵素原子、氰基、取代或無取代之碳數1~20之烷基、取代或無取代之碳數2~20之烯基、取代或無取代之碳數2~20之炔基、取代或無取代之甲矽烷基、取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基。 In the above general formula (43), R 21 to R 28 each represent a hydrogen atom, a halogen atom, a cyano-substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted methyroalkyl group, or a substituted or none. Substituted to form an aromatic hydrocarbon group having 6 to 30 carbon atoms, R 218 to R 241 each represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted. Alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted methylosyl group, substituted or unsubstituted ring-forming aromatic hydrocarbon group having 6 to 30 carbon atoms, Or a substituted or unsubstituted heterocyclic group having 5 to 30 atoms in the ring.

X22及X23係選自氧原子或硫原子之任一。 X 22 and X 23 are selected from either an oxygen atom or a sulfur atom.

前述一般式(43)中之鹵素原子、芳香族烴基、雜環基、烷基、烷氧基、芳氧基、芳基硫基、芳基胺基,例如有前述一般式(1)~(20)、(51)~(62)所說明之基團。 The halogen atom, aromatic hydrocarbon group, heterocyclic group, alkyl group, alkoxy group, aryloxy group, arylthio group or arylamine group in the above general formula (43), for example, has the above general formula (1) to ( 20), the groups described in (51) ~ (62).

前述一般式(43)中之甲矽烷基,例如有以前述一般式(41)、(42)所說明之基團。 The mercaptoalkyl group in the above general formula (43) is, for example, a group described in the above general formulas (41) and (42).

前述一般式(43)中之碳數2~20之烯基及前述一般式(43)中之碳數2~20之炔基,例如有以前述一般式(41)、(42)所說明之基團。 The alkenyl group having 2 to 20 carbon atoms in the above general formula (43) and the alkynyl group having 2 to 20 carbon atoms in the above general formula (43) are, for example, described in the above general formulas (41) and (42). Group.

前述一般式(43)中,R21~R28較佳為氫原子。 In the above general formula (43), R 21 to R 28 are preferably a hydrogen atom.

前述一般式(43)之R22及R26為取代或無取代之碳數1~20之烷基、或取代或無取代之碳數3~30之烷基甲矽烷基,R21、R23、R24、R25、R27、R28更佳為氫原子。 R 22 and R 26 in the above general formula (43) are a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkylcarbenyl group having 3 to 30 carbon atoms, R 21 and R 23 . R 24 , R 25 , R 27 and R 28 are more preferably a hydrogen atom.

又,前述一般式(43)之X22及X23較佳為氧原子。 Further, X 22 and X 23 of the above general formula (43) are preferably an oxygen atom.

又,前述一般式(43)之較佳形態,例如R221及R228為選自氫原子、鹵素原子、取代或無取代之碳數1~20之烷基、取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基者。 Further, in a preferred embodiment of the above general formula (43), for example, R 221 and R 228 are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted ring. An aromatic hydrocarbon group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 atomic number of atoms.

又,前述一般式(43)之較佳形態,例如R232~R236之中0個、1個或2個為選自取代或無取代之碳數1~20之烷基或取代或無取代之形成環之碳數6~30之芳香族烴基,而R237~R241之中0個、1個或2個為選自取代或無取代之碳數1~20之烷基或取代或無取代之形成環之碳數6~30之芳香族烴基者。 Further, in a preferred embodiment of the above general formula (43), for example, 0, 1 or 2 of R 232 to R 236 are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms or substituted or unsubstituted. The ring forms a carbon number of 6 to 30 aromatic hydrocarbon groups, and 0, 1 or 2 of R 237 to R 241 are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms or substituted or absent. Substituting an aromatic hydrocarbon group having 6 to 30 carbon atoms forming a ring.

以下表示前述一般式(41)表示之芘衍生物之具體例,但是本發明不限於此等例示化合物。 Specific examples of the anthracene derivative represented by the above general formula (41) are shown below, but the present invention is not limited to the above-exemplified compounds.

本實施形態中,摻雜劑材料在發光層中之含量,無特別限定,可配合目的適當選擇,例如較佳為0.1質量%以上、70質量%以下,更佳為1質量%以上、30質量%以下。摻雜劑材料之含量在0.1質量%以上時,可得到充分的發光,在70質量%以下時,可避免濃度消光。 In the present embodiment, the content of the dopant material in the light-emitting layer is not particularly limited, and may be appropriately selected in accordance with the purpose, and is, for example, preferably 0.1% by mass or more and 70% by mass or less, more preferably 1% by mass or more and 30% by mass. %the following. When the content of the dopant material is 0.1% by mass or more, sufficient light emission can be obtained, and when it is 70% by mass or less, concentration extinction can be avoided.

本實施形態中,發光層所含之摻雜劑材料,其發光色無特別限定,但是以顯示主波峰波長為480nm以下之藍色發光之螢光發光性之摻雜劑材料為佳。主波峰波長係指在濃度10-6莫耳/升以上、10-5莫耳/升以下之甲苯溶液中所測定之發光光譜中之發光強度成為最大之發光光譜之波峰波長。 In the present embodiment, the dopant color of the dopant material contained in the light-emitting layer is not particularly limited, but a dopant material having a fluorescent property of blue light emission having a main peak wavelength of 480 nm or less is preferable. The main peak wavelength refers to the peak wavelength of the luminescence spectrum in which the luminescence intensity in the luminescence spectrum measured in the toluene solution having a concentration of 10 -6 mol/liter or more and 10 -5 mol/liter or less is the maximum.

將這種主波峰波長之摻雜劑材料摻雜於前述一般式(1)表示之主體材料中,構成發光層時,有機EL元件變成高效率且長壽命。 When the dopant material of the main peak wavelength is doped into the host material represented by the above general formula (1) to form a light-emitting layer, the organic EL element becomes highly efficient and has a long life.

.主體材料及摻雜劑材料之組合 . Combination of host material and dopant material

本實施形態中,主體材料使用前述一般式(1)之Z1為前述一般式(5)~(10)表示之蒽衍生物較佳,特佳為Z1使用前述一般式(8)~(10)表示之萘並苯並呋喃。萘並苯並呋喃 取代蒽時,推測因萘並苯並呋喃之平面性,因此提高發光層中之分子間之堆疊(packing),因而電荷移動度變高。此時,電荷由發光層中漏出,可能使效率及壽命降低。因此,使用具有電子或電洞捕捉(trap)性,且具有縮合環結構之摻雜劑,可將載體(carrier)封閉於在發光層內,可達成高效率且長壽命。將具有電子捕捉性,且具有縮合環結構之一般式(41)表示之化合物(二胺基芘衍生物)作為摻雜劑材料使用,可將電荷封閉於發光層內,可達成高效率化及長壽命化。 In the present embodiment, the host material is preferably an anthracene derivative represented by the above general formulas (5) to (10) using Z 1 of the above general formula (1), and particularly preferably Z 1 is the above general formula (8) to ((). 10) represents naphthobenzofuran. When naphthobenzofuran is substituted for hydrazine, it is presumed that due to the planarity of naphthobenzofuran, the packing between the molecules in the light-emitting layer is improved, and thus the degree of charge mobility becomes high. At this time, electric charges are leaked from the light-emitting layer, which may lower efficiency and life. Therefore, by using a dopant having electron or hole trapping property and having a condensed ring structure, a carrier can be enclosed in the light-emitting layer, and high efficiency and long life can be achieved. When a compound (diamine fluorene derivative) represented by the general formula (41) having an electron-trapping property and having a condensed ring structure is used as a dopant material, the charge can be enclosed in the light-emitting layer, and high efficiency can be achieved. Long life.

[實施形態之變形] [Modification of Embodiment]

本發明不限於上述實施形態者,可達成本發明之目的之範圍之變更、改良等,均包含在本發明內者。 The present invention is not limited to the above-described embodiments, and modifications, improvements, etc., which are within the scope of the invention, are included in the present invention.

發光層不限於1層,可層合複數之發光層。有機EL元件具有複數之發光層時,至少1層之發光層只要含有前述一般式(1)表示之化合物與前述一般式(21)或前述一般式(41)表示之化合物即可,其他的發光層可為螢光發光型之發光層或磷光發光型之發光層。 The light-emitting layer is not limited to one layer, and a plurality of light-emitting layers may be laminated. When the organic EL device has a plurality of light-emitting layers, at least one of the light-emitting layers may contain a compound represented by the above formula (1) and a compound represented by the above general formula (21) or the general formula (41), and other light-emitting layers may be used. The layer may be a fluorescent light emitting layer or a phosphorescent emitting layer.

又,有機EL元件具有複數之發光層時,此等發光層可彼此鄰接設置,或介隔中間層,層合有複數之發光單元,即串聯(Tandem)式之有機EL元件。 Further, when the organic EL element has a plurality of light-emitting layers, the light-emitting layers may be disposed adjacent to each other or may be laminated with a plurality of light-emitting units, that is, tandem organic EL elements.

本發明中,上述發光層較佳為含有電荷注入補助劑。 In the present invention, the light-emitting layer preferably contains a charge injection auxiliary agent.

使用能隙較廣之主體材料形成發光層時,主體材料之離子化能量(Ip:ionization potential)與電洞注入、輸送層 等之Ip之差變大,電洞注入發光層變得困難,欲得到充分之亮度所需之驅動電壓有上昇之疑慮。 When a light-emitting layer is formed using a host material having a wide energy gap, the difference between the ionization energy ( Ip : ionization potential) of the host material and the Ip of the hole injection and transport layer becomes large, and it becomes difficult to inject the light-emitting layer into the hole. There is a concern that the driving voltage required to obtain sufficient brightness rises.

這種情形下,藉著使發光層中含有電洞注入、輸送性之電荷注入補助劑,使電洞容易注入發光層,可降低驅動電壓。 In this case, the hole is easily injected into the light-emitting layer by injecting a charge injecting and transporting a charge into the light-emitting layer, thereby lowering the driving voltage.

電荷注入補助劑可利用例如一般的電洞注入、輸送材料等。 The charge injection auxiliary agent can be, for example, a general hole injection, a material to be transported, or the like.

具體例有三唑衍生物、噁二唑衍生物、咪唑衍生物、聚芳烷衍生物、吡唑啉衍生物及吡唑啉酮衍生物、苯二胺衍生物、芳基胺衍生物、胺基取代查耳酮衍生物、噁唑衍生物、茀酮衍生物、腙衍生物、茋衍生物、矽胺烷衍生物、聚矽烷系、苯胺系共聚物、導電性高分子寡聚物(特別是噻吩寡聚物)等。 Specific examples thereof include a triazole derivative, an oxadiazole derivative, an imidazole derivative, a polyaralkyl derivative, a pyrazoline derivative, and a pyrazolone derivative, a phenylenediamine derivative, an arylamine derivative, and an amine group. Instead of a chalcone derivative, an oxazole derivative, an anthrone derivative, an anthracene derivative, an anthracene derivative, a decane derivative, a polydecane system, an aniline copolymer, or a conductive polymer oligomer (especially Thiophene oligomers) and the like.

電洞注入性之材料例如有上述者,較佳為卟啉化合物、芳香族三級胺化合物及苯乙烯基胺化合物,特佳為芳香族三級胺化合物。 The material for the hole injecting property is, for example, the above, preferably a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound, and particularly preferably an aromatic tertiary amine compound.

另外,分子內具有2個縮合芳香族環,例如4,4’-雙(N-(1-萘基)-N-苯基胺基)聯苯(以下簡稱NPD),三苯胺單元連結成3個星芒型之4,4’,4”-三(N-(3-甲基苯基)-N-苯基胺基)三苯胺(以下簡稱MTDATA)等。 Further, there are two condensed aromatic rings in the molecule, for example, 4,4'-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (hereinafter abbreviated as NPD), and the triphenylamine units are bonded to 3 4,4',4"-tris(N-(3-methylphenyl)-N-phenylamino)triphenylamine (hereinafter referred to as MTDATA).

另外,六氮雜三亞苯衍生物等,也可適合作為電洞注入性之材料使用。 Further, a hexaazatriphenylene derivative or the like can also be suitably used as a material for hole injectability.

另外,p型Si、p型SiC等無機化合物也可作為電洞注入材料使用。 Further, an inorganic compound such as p-type Si or p-type SiC can also be used as a hole injecting material.

本發明之有機EL元件可適合作為電視、行動電話、或個人電腦等之顯示裝置、或照明、或車輛用燈具之發光裝置等之電子機器使用。 The organic EL device of the present invention can be suitably used as a display device for a television, a mobile phone, or a personal computer, or an electronic device such as a lighting device or a lighting device for a vehicle lamp.

〔實施例〕 [Examples]

其次,說明本發明之實施例,但是本發明不限於此等實施例。 Next, an embodiment of the present invention will be described, but the present invention is not limited to the embodiments.

[化合物之合成] [Synthesis of Compounds] 合成例1 化合物1之合成 Synthesis Example 1 Synthesis of Compound 1

依據下述圖解(Scheme)合成化合物1。 According to the following scheme (Scheme) Synthesis of compound 1.

(1-1)4-苯基-2-甲基苯胺之合成 (1-1) Synthesis of 4-phenyl-2-methylaniline

氬氣氛下,將4-溴-2-甲基苯胺(5.00g)、苯基硼酸(4.26g)、肆(三苯基膦)鈀(0)(1.60g)、甲苯(67mL)、1,2-二 甲氧基乙烷(67mL)及2M碳酸鈉水溶液54mL之混合物,迴流15小時。將所得之反應混合物冷卻至室溫後,使用甲苯萃取。有機層以飽和食鹽水洗淨,使用無水硫酸鈉乾燥後,減壓餾除溶劑。所得之殘渣以矽膠管柱層析法純化,得到4-苯基-2-甲基苯胺(4.74g)。收率為96%。 4-bromo-2-methylaniline (5.00 g), phenylboronic acid (4.26 g), hydrazine (triphenylphosphine) palladium (0) (1.60 g), toluene (67 mL), 1, under argon atmosphere. 2-two A mixture of methoxyethane (67 mL) and aq. After the resulting reaction mixture was cooled to room temperature, it was extracted with toluene. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue obtained was purified by silica gel column chromatography to give 4-phenyl-2-methylaniline (4.74 g). The yield was 96%.

(1-2)N-(2-甲基-4-苯基苯基)二苯並呋喃-4-胺之合成 Synthesis of (1-2) N-(2-methyl-4-phenylphenyl)dibenzofuran-4-amine

氬氣氛下,將(1-1)所得之4-苯基-2-甲基苯胺(4.50g)、4-溴二苯並呋喃(3.20g)、三(二苄叉丙酮(benzylideneacetone))二鈀(0)(0.18g)、BINAP(2,2’-雙(二苯基膦基(phosphino))-1,1’-雙萘基)(0.24g)、鈉-t-丁醇鹽(2.50g)及甲苯(87mL)之混合物,在90℃下迴流8小時。所得之反應混合物冷卻至室溫,使用矽藻土過濾,減壓餾除溶劑。所得之殘渣以矽膠管柱層析法純化,得到N-(2-甲基-4-苯基苯基)二苯並呋喃-4-胺(3.28g)。收率為72%。 4-phenyl-2-methylaniline (4.50 g), 4-bromodibenzofuran (3.20 g), and tris(benzylideneacetone) II obtained in (1-1) under an argon atmosphere Palladium (0) (0.18 g), BINAP (2,2'-bis(diphenylphosphino)-1,1'-bisnaphthyl) (0.24 g), sodium-t-butoxide ( A mixture of 2.50 g) and toluene (87 mL) was refluxed at 90 ° C for 8 hours. The obtained reaction mixture was cooled to room temperature, filtered over Celite, and evaporated. The residue thus obtained was purified by silica gel column chromatography to give N-(2-methyl-4-phenylphenyl)dibenzofuran-4-amine (3.28 g). The yield was 72%.

(1-3)化合物1之合成 (1-3) Synthesis of Compound 1

氬氣氛下,將(1-2)所得之N-(2-甲基-4-苯基苯基)二苯並呋喃-4-胺(3.26g)、1,6-二溴芘(1.40g)、三(二苄叉丙酮)二鈀(0)(0.11g)、三-t-丁基膦(0.08g)、鈉-t-丁醇鹽(2.50g)及甲苯(19mL)之混合物,在85℃下攪拌8小時。所得之反應混合物冷卻至室溫,使用矽藻土過濾,減壓餾除溶劑。所得之殘渣以矽膠管柱層析法及再結晶純化,得到化合物1(2.54g)。收率為73%。所得之化合物使用質譜 儀(mass spectrometry,MS)確認,相對於分子量896.34,m/e=896。 N-(2-methyl-4-phenylphenyl)dibenzofuran-4-amine (3.26 g) and 1,6-dibromofluorene (1.40 g) obtained in (1-2) under an argon atmosphere. a mixture of tris(dibenzylideneacetone)dipalladium(0) (0.11 g), tri-t-butylphosphine (0.08 g), sodium-t-butoxide (2.50 g) and toluene (19 mL), Stir at 85 ° C for 8 hours. The obtained reaction mixture was cooled to room temperature, filtered over Celite, and evaporated. The residue thus obtained was purified by silica gel column chromatography and recrystallization to give Compound 1 (2.54 g). The yield was 73%. The obtained compound uses mass spectrometry The mass spectrometry (MS) confirmed that m/e = 896 with respect to the molecular weight of 896.34.

合成例2 化合物2之合成 Synthesis Example 2 Synthesis of Compound 2

合成例1中,除使用4-溴-3-甲基苯胺取代4-溴-2-甲基苯胺外,進行同樣的操作得到化合物2。所得之化合物以質譜儀確認,相對於分子量896.34,m/e=896。 In Synthesis Example 1, except that 4-bromo-3-methylaniline was used instead of 4-bromo-2-methylaniline, the same operation was carried out to obtain Compound 2. The obtained compound was confirmed by a mass spectrometer, m/e = 896 with respect to a molecular weight of 896.34.

合成例3 化合物3之合成 Synthesis Example 3 Synthesis of Compound 3

合成例1中,除使用5-溴-2-甲基苯胺取代4-溴-2-甲基苯胺,進行同樣的操作得到化合物3。所得之化合物以質譜儀確認,相對於分子量896.34,m/e=896。 In Synthesis Example 1, except that 5-bromo-2-methylaniline was used instead of 4-bromo-2-methylaniline, the same operation was carried out to obtain Compound 3. The obtained compound was confirmed by a mass spectrometer, m/e = 896 with respect to a molecular weight of 896.34.

合成例4 化合物4之合成 Synthesis Example 4 Synthesis of Compound 4

合成例1中,除使用3-溴-2-甲基苯胺取代4-溴-2-甲基苯胺外,進行同樣的操作得到化合物4。所得之化合物以質譜儀確認,相對於分子量896.34,m/e=896。 In Synthesis Example 1, except that 3-bromo-2-methylaniline was used instead of 4-bromo-2-methylaniline, the same operation was carried out to obtain Compound 4. The obtained compound was confirmed by a mass spectrometer, m/e = 896 with respect to a molecular weight of 896.34.

合成例5 化合物5之合成 Synthesis Example 5 Synthesis of Compound 5

合成例1中,除使用3-溴-4-甲基苯胺取代4-溴-2-甲基苯胺外,進行同樣的操作得到化合物5。所得之化合物以質譜儀確認,相對於分子量896.34,m/e=896。 In Synthesis Example 1, except that 3-bromo-4-methylaniline was used instead of 4-bromo-2-methylaniline, the same operation was carried out to obtain Compound 5. The obtained compound was confirmed by a mass spectrometer, m/e = 896 with respect to a molecular weight of 896.34.

合成例6 化合物6之合成 Synthesis Example 6 Synthesis of Compound 6

合成例1中,除使用2-溴-4-甲基苯胺取代4-溴-2-甲基苯胺外,進行同樣的操作得到化合物6。所得之化合物以質譜儀確認,相對於分子量896.34,m/e=896。 In Synthesis Example 1, except that 2-bromo-4-methylaniline was used instead of 4-bromo-2-methylaniline, the same operation was carried out to give Compound 6. The obtained compound was confirmed by a mass spectrometer, m/e = 896 with respect to a molecular weight of 896.34.

中間體合成例1 中間體A之合成 Intermediate Synthesis Example 1 Synthesis of Intermediate A

依據下述圖解(Scheme)合成中間體A。 According to the following scheme (Scheme) Synthesis of Intermediate A.

(A-1)4-苯基二苯並呋喃之合成 Synthesis of (A-1) 4-phenyldibenzofuran

氬氣氛下,將4-溴二苯並呋喃(400g)、苯基硼酸(267g)、肆(三苯基膦)鈀(0)(56.2g)、碳酸鈉(515g)、1,2-二甲氧基乙烷(4000mL)及水(2340mL)之混合物,迴流16小時。將所得之反應混合物冷卻至室溫後,使用乙酸乙酯萃取,減壓餾除溶劑。所得之殘渣以矽膠管柱層析法純化,得到4-苯基二苯並呋喃(383g)。收率為97%。 4-bromodibenzofuran (400 g), phenylboronic acid (267 g), hydrazine (triphenylphosphine) palladium (0) (56.2 g), sodium carbonate (515 g), 1,2-di under argon atmosphere A mixture of methoxyethane (4000 mL) and water (2340 mL) was refluxed for 16 h. The obtained reaction mixture was cooled to room temperature and then extracted with ethyl acetate. The residue obtained was purified by silica gel column chromatography to give 4-phenyldibenzofuran (383 g). The yield was 97%.

(A-2)中間體A之合成 (A-2) Synthesis of Intermediate A

氬氣氛下,將(A-1)所得之4-苯基二苯並呋喃(250g)之四氫呋喃(1875mL)溶液冷卻至-10℃,將1.6M正丁基鋰己烷溶液(704mL)滴下,反應液在10℃下攪拌1.5小時。使反應液冷卻至-60℃,將1,2-二溴乙烷(289g)滴下添加,使反應液返回室溫,攪拌1日。將水加入所得之反應混合物中,使用乙酸乙酯萃取,減壓餾除溶劑。所得之殘渣以矽膠管柱層析法及再結晶純化,得到中間體A(137g)。收率為41%。 A solution of 4-phenyldibenzofuran (250 g) obtained in (A-1) in tetrahydrofuran (1875 mL) was cooled to -10 ° C under argon atmosphere, and 1.6 M n-butyllithium hexane solution (704 mL) was dropped. The reaction solution was stirred at 10 ° C for 1.5 hours. The reaction liquid was cooled to -60 ° C, and 1,2-dibromoethane (289 g) was added dropwise, and the reaction liquid was returned to room temperature, and stirred for 1 day. Water was added to the obtained reaction mixture, and extracted with ethyl acetate. The residue obtained was purified by silica gel column chromatography and recrystallization to afford Intermediate A (137 g). The yield was 41%.

合成例7 化合物7之合成 Synthesis Example 7 Synthesis of Compound 7

依據下述圖解(Scheme)合成化合物7。 According to the following scheme (Scheme) Synthesis of compound 7.

(7-1)6-苯基-N-(p-甲苯基(tolyl))二苯並呋喃-4-胺之合成 Synthesis of (7-1) 6-phenyl-N-(p-tolyl)dibenzofuran-4-amine

氬氣氛下,將p-甲苯胺(7.59g)、中間體合成例1所得之中間體A(11.45g)、三(二苄叉丙酮)二鈀(0)(0.49g)、BINAP(0.66g)、鈉-t-丁醇鹽(6.81g)及甲苯(177mL)之混合物,在90℃下迴流6.5小時。將所得之反應混合物冷卻至室溫,使用矽藻土過濾,減壓餾除溶劑。所得之殘渣以矽膠管柱層析法純化,得到6-苯基-N-(p-甲苯基(tolyl))二苯並呋喃-4-胺(11.12g)。收率為90%。 P-toluidine (7.59 g), Intermediate A (11.45 g) obtained in Intermediate Synthesis Example 1, tris(dibenzylideneacetone) dipalladium (0) (0.49 g), BINAP (0.66 g) under argon atmosphere A mixture of sodium-t-butoxide (6.81 g) and toluene (177 mL) was refluxed at 90 ° C for 6.5 hours. The obtained reaction mixture was cooled to room temperature, filtered over Celite, and evaporated. The residue obtained was purified by silica gel column chromatography to give 6-phenyl-N-(p-tolyl)dibenzofuran-4-amine (11.12 g). The yield was 90%.

(7-2)化合物7之合成 (7-2) Synthesis of Compound 7

氬氣氛下,將(7-1)所得之6-苯基-N-(p-甲苯基(tolyl))二苯並呋喃-4-胺(11.12g)、1,6-二溴芘(4.77g)、三(二苄叉丙酮)二鈀(0)(0.36g)、三-t-丁基膦(0.27g)、鈉-t-丁醇鹽(3.81g)及甲苯(66mL)之混合物,迴流8小時。所得之反應混合物冷卻至室溫,添加甲醇(132mL),經攪拌後,由反應混合物過濾取得沈澱。將所得之濾取物以矽膠管柱層析法及再結晶純化,得到化合物7(9.19g)。收率為77%。所得之化合物使用質譜儀確認,相對於分子量896.34,m/e=896。 6-phenyl-N-(p-tolyl)dibenzofuran-4-amine (11.12 g) and 1,6-dibromofluorene (4.77) obtained in (7-1) under an argon atmosphere. g), a mixture of tris(dibenzylideneacetone)dipalladium(0) (0.36 g), tri-t-butylphosphine (0.27 g), sodium-t-butoxide (3.81 g) and toluene (66 mL) , reflux for 8 hours. The obtained reaction mixture was cooled to room temperature, and methanol (132 mL) was added, and after stirring, the mixture was filtered to obtain a precipitate. The obtained filtrate was purified by silica gel column chromatography and recrystallization to give Compound 7 (9.19 g). The yield was 77%. The obtained compound was confirmed using a mass spectrometer, m/e = 896 with respect to a molecular weight of 896.34.

合成例8 化合物8之合成 Synthesis Example 8 Synthesis of Compound 8

合成例7中,使用m-甲苯胺取代p-甲苯胺外,進行同樣操作,得到化合物8。所得之化合物使用質譜儀確認,相對於分子量896.34,m/e=896。 In Synthesis Example 7, except that m-toluidine was used instead of p-toluidine, the same operation was carried out to obtain Compound 8. The obtained compound was confirmed using a mass spectrometer, m/e = 896 with respect to a molecular weight of 896.34.

合成例9 化合物9之合成 Synthesis Example 9 Synthesis of Compound 9

合成例7中,使用o-甲苯胺取代p-甲苯胺外,進行同樣操作,得到化合物9。所得之化合物使用質譜儀確認,相對於分子量896.34,m/e=896。 In Synthesis Example 7, except that o-toluidine was used instead of p-toluidine, the same operation was carried out to obtain Compound 9. The obtained compound was confirmed using a mass spectrometer, m/e = 896 with respect to a molecular weight of 896.34.

合成例10 化合物10之合成 Synthesis Example 10 Synthesis of Compound 10

合成例7中,使用3,5-二甲基苯胺取代p-甲苯胺外,進行同樣操作,得到化合物10。所得之化合物使用質譜儀確認,相對於分子量924.37,m/e=924。 In Synthesis Example 7, except that 3,5-dimethylaniline was used instead of p-toluidine, the same procedure was carried out to obtain Compound 10. The obtained compound was confirmed using a mass spectrometer, m/e = 924 with respect to a molecular weight of 924.37.

合成例11 化合物11之合成 Synthesis Example 11 Synthesis of Compound 11

合成例7中,使用3,4-二甲基苯胺取代p-甲苯胺外,進行同樣操作,得到化合物11。所得之化合物使用質譜儀確認,相對於分子量924.37,m/e=924。 In Synthesis Example 7, except that 3,4-dimethylaniline was used instead of p-toluidine, the same operation was carried out to obtain Compound 11. The obtained compound was confirmed using a mass spectrometer, m/e = 924 with respect to a molecular weight of 924.37.

[有機EL元件之製造] [Manufacture of Organic EL Elements]

使用的化合物如下述。 The compounds used are as follows.

(實施例1) (Example 1)

將25mm×75mm×1.1mm厚之附有ITO透明電極(陽極)之玻璃基板(geomatec公司製)在異丙醇中進行5分鐘超音波洗淨後,進行UV臭氧洗淨30分鐘。ITO之膜厚為130nm。 A glass substrate (manufactured by Geomatec Co., Ltd.) having a thickness of 25 mm × 75 mm × 1.1 mm and having an ITO transparent electrode (anode) was ultrasonically washed in isopropyl alcohol for 5 minutes, and then washed by UV ozone for 30 minutes. The film thickness of ITO was 130 nm.

將洗淨後之附有透明電極線之玻璃基板安裝於真空蒸鍍裝置之基板架上,首先,於形成有透明電極線之側的面上,蒸鍍化合物HA-1,形成膜厚5nm的化合物HA-1 膜,以覆蓋透明電極。此HA-1膜係作為電洞注入層的功能。 The glass substrate with the transparent electrode wire after the cleaning is attached to the substrate holder of the vacuum vapor deposition apparatus. First, the compound HA-1 is vapor-deposited on the surface on the side where the transparent electrode line is formed to form a film thickness of 5 nm. Compound HA-1 Membrane to cover the transparent electrode. This HA-1 film functions as a hole injection layer.

HA-1膜之成膜後,接著蒸鍍化合物HT-1,在HA-1膜上形成膜厚95nm的HT-1膜。此HT-1膜係作為電洞輸送層的功能。 After the film formation of the HA-1 film, the compound HT-1 was vapor-deposited, and an HT-1 film having a film thickness of 95 nm was formed on the HA-1 film. This HT-1 film functions as a hole transport layer.

其次,此HT-1膜上共同蒸鍍化合物BH-1(主體材料)及化合物BD-1(摻雜劑材料),形成膜厚25nm之發光層膜。此發光層中,主體材料濃度為95質量%,摻雜劑材料濃度為5質量%。 Next, the compound BH-1 (host material) and the compound BD-1 (dopant material) were co-deposited on the HT-1 film to form a light-emitting layer film having a film thickness of 25 nm. In the light-emitting layer, the host material concentration was 95% by mass, and the dopant material concentration was 5% by mass.

此發光層上蒸鍍電子輸送性化合物ET-1,形成膜厚25nm之電子輸送層。 The electron transporting compound ET-1 was deposited on the light emitting layer to form an electron transporting layer having a film thickness of 25 nm.

此電子輸送層上蒸鍍LiF,形成厚度1nm的LiF層。 LiF was deposited on this electron transport layer to form a LiF layer having a thickness of 1 nm.

此LiF膜上蒸鍍金屬Al,形成厚度80nm之金屬Al的陰極。 Metal Al was vapor-deposited on this LiF film to form a cathode of metal Al having a thickness of 80 nm.

(實施例2) (Example 2)

實施例2之有機EL元件除了將構成發光層之材料變更為化合物BH-1(主體材料)及化合物BD-2(摻雜劑材料)外,與實施例1同樣製作有機EL元件。 In the organic EL device of Example 2, an organic EL device was produced in the same manner as in Example 1 except that the material constituting the light-emitting layer was changed to the compound BH-1 (host material) and the compound BD-2 (dopant material).

(比較例1~4) (Comparative examples 1 to 4)

比較例1~4之有機EL元件,各自如表11所示,除變更發光層中之材料外,其餘與實施例1同樣製作有機EL元件。 In the organic EL devices of Comparative Examples 1 to 4, as shown in Table 11, an organic EL device was produced in the same manner as in Example 1 except that the materials in the light-emitting layer were changed.

〔有機EL元件之評價〕 [Evaluation of Organic EL Elements]

對於製作後之有機EL元件,外加電壓,使電流密度成為10mA/cm2,然後評價驅動電壓、CIE1931色度、電流效率L/J、外部量子效率EQE、及主波峰波長λp。此外,外加電壓,使電流密度成為50mA/cm2,然後評價壽命LT90。結果如表11所示。對於CIE1931色度及主波峰波長λp以外之各評價項目係計算實施例1、2及比較例1~4之各評價項目之值相對於比較例1之各評價項目之值之比而得的值。 For the organic EL element after fabrication, a voltage was applied to make the current density 10 mA/cm 2 , and then the driving voltage, CIE 1931 chromaticity, current efficiency L/J, external quantum efficiency EQE, and main peak wavelength λ p were evaluated. Further, a voltage was applied to make the current density 50 mA/cm 2 , and then the life LT90 was evaluated. The results are shown in Table 11. For each of the evaluation items other than the CIE 1931 chromaticity and the main peak wavelength λ p , the ratio of the values of the evaluation items of Examples 1 and 2 and Comparative Examples 1 to 4 to the values of the respective evaluation items of Comparative Example 1 was calculated. value.

.驅動電壓 . Driving voltage

使電流密度成為10mA/cm2的狀態,量測於ITO透明電極與金屬Al陰極之間通電時的電壓(單位:V)。 The current density was set to 10 mA/cm 2 , and the voltage (unit: V) at the time of energization between the ITO transparent electrode and the metal Al cathode was measured.

.CIE1931色度 . CIE1931 color

使電流密度成為10mA/cm2的狀態,對於元件施加電壓時之CIE1931色度座標(x、y),使用分光放射亮度計CS-1000(Konica Minolta公司製)量測。 The current density was set to 10 mA/cm 2 , and the CIE 1931 chromaticity coordinates (x, y) when a voltage was applied to the element were measured using a spectroradiometer CS-1000 (manufactured by Konica Minolta Co., Ltd.).

.電流效率L/J . Current efficiency L/J

使電流密度成為10mA/cm2的狀態,對於元件施加電壓時之分光放射亮度光譜,使用上述分光放射亮度計量測,由所得之分光放射亮度光譜算出電流效率(單位:cd/A)。 The current density was set to 10 mA/cm 2 , and the spectral radiance spectrum when the voltage was applied to the element was measured by the above-described spectral radiance measurement, and the current efficiency (unit: cd/A) was calculated from the obtained spectral luminescence spectrum.

.外部量子效率EQE . External quantum efficiency EQE

由所得之上述分光放射亮度光譜,假設已進行朗伯 (Lambertian) 放射,算出外部量子效率EQE(單位:%)。 From the above-mentioned spectral radiance spectrum, it is assumed that Lambert has been performed. (Lambertian) The external quantum efficiency EQE (unit: %) was calculated by radiation.

.主波峰波長λ p . Main peak wavelength λ p

由所得之上述分光放射亮度光譜,得到主波峰波長λp(單位:nm)。 From the obtained spectral radiance spectrum, the main peak wavelength λ p (unit: nm) was obtained.

.壽命LT90 . Life LT90

使電流密度成為50mA/cm2的狀態,對元件外加電壓,相對於初期亮度時,量測亮度成為90%為止的時間(單位:h)。 When the current density was 50 mA/cm 2 , the voltage was applied to the element, and the time until the initial brightness was measured was 90% (unit: h).

上述實施例1係將前述一般式(1)表示之蒽衍生物作為主體材料使用,以前述一般式(21)表示之衍生物作為摻雜劑材料使用的有機EL元件,相較於使用本案以外之主體材料及摻雜劑材料的比較例1時,為更低電壓,但是能大幅提高效率、壽命。 In the above-mentioned Example 1, the anthracene derivative represented by the above general formula (1) is used as a host material, and is represented by the above general formula (21). The organic EL device used as the dopant material of the derivative has a lower voltage than the comparative example 1 using the host material and the dopant material other than the above, but can greatly improve the efficiency and the lifetime.

同樣地,上述實施例2係將前述一般式(1)表示之蒽衍生物作為主體材料使用,將前述一般式(41)表示之芘衍生物作為摻雜劑材料使用的有機EL元件,相對於比較例1時,為更低電壓,但是能大幅提高效率、壽命。 In the same manner, the above-mentioned Example 2 is an organic EL device in which the anthracene derivative represented by the above general formula (1) is used as a host material, and the anthracene derivative represented by the above general formula (41) is used as a dopant material. In Comparative Example 1, the voltage was lower, but the efficiency and life were greatly improved.

比較例2係使用與實施例1及實施例2相同之主體材料的有機EL元件。 In Comparative Example 2, an organic EL device using the same host material as in Example 1 and Example 2 was used.

比較例3及比較例4係使用與一般式(1)表示蒽衍生物不同結構之蒽化合物的有機EL元件。 In Comparative Example 3 and Comparative Example 4, an organic EL device having a ruthenium compound having a different structure from the general formula (1).

實施例1及實施例2的有機EL元件,即使相較於比較例2~4時,可維持低電壓,且更提高效率及壽命。特別是實施例1係相較於比較例2時,以同等的低電壓驅動,但是能大幅提高效率及壽命。又,實施例2相較於比較例2時,以同等的低電壓驅動,但是能大幅提高外部量子效率EQE及壽命。 In the organic EL devices of the first embodiment and the second embodiment, even when compared with the comparative examples 2 to 4, the low voltage can be maintained, and the efficiency and the life can be further improved. In particular, Example 1 was driven at the same low voltage as compared with Comparative Example 2, but the efficiency and life were greatly improved. Further, in the second embodiment, the second embodiment is driven at the same low voltage as compared with the second comparative example, but the external quantum efficiency EQE and the lifetime can be greatly improved.

1‧‧‧陰極 1‧‧‧ cathode

2‧‧‧電子輸送層 2‧‧‧Electronic transport layer

3‧‧‧發光層 3‧‧‧Lighting layer

4‧‧‧電洞輸送層 4‧‧‧ hole transport layer

5‧‧‧陽極 5‧‧‧Anode

6‧‧‧基板 6‧‧‧Substrate

Claims (18)

一種有機電致發光元件,其特徵係具有陰極;陽極;配置於前述陰極與前述陽極之間,至少含有發光層之1層以上的有機層;前述發光層為含有以下述一般式(1)表示之蒽衍生物與以下述一般式(21)表示之衍生物, [前述一般式(1)中,R1~R10之任意c個係用於與L1鍵結的單鍵,未用於與L1鍵結的R1~R10各自為選自氫原子、鹵素原子、羥基、氰基、取代或無取代之胺基、取代或無取代之碳數1~20之烷基、取代或無取代之碳數1~20之烷氧基、取代或無取代之形成環之碳數6~30之芳氧基、取代或無取代之形成環之碳數6~30之芳硫基、取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基之任 一,L1係選自單鍵或連結基之任一,前述連結基係取代或無取代之形成環之碳數6~30之(a+1)價之芳香族烴基、取代或無取代之形成環之原子數5~30之(a+1)價之雜環基、或前述取代或無取代之形成環之碳數6~30之芳香族烴基及前述取代或無取代之形成環之原子數5~30之雜環基所選出之基團2~4個鍵結形成之(a+1)價基團,a、b、c各自表示1~4之整數,Z1係以下述一般式(2)表示] [前述一般式(2)中,X1係選自氧原子或硫原子之任一,R111~R118各自與前述一般式(1)中,未用於與L1鍵結的R1~R10同義,但是R111與R112、R112與R113、R113與R114、R115與R116、R116與R117或R117與R118之中至少1組之鄰接的2個取代基,互相鍵結形成以下述一般式(3)或(4)表示之環] [前述一般式(3)中,y1、y2表示選自前述一般式(2)之R111~R118的鍵結位置,前述一般式(4)中,y3、y4表示選自前述一般式(2)之R111~R118的鍵結位置,R121~R124、R125~R128各自與前述一般式(1)中,未用於與L1鍵結之R1~R10同義,X2係選自氧原子或硫原子之任一,前述一般式(2)中,未形成環之R111~R118及前述一般式(3)之R121~R124之任一個或前述一般式(2)中,未形成環之R111~R118及前述一般式(4)之R125~R128之任一個為單鍵,用於與前述一般式(1)之L1鍵結] [前述一般式(21)中,R20~R29各自表示為氫原子、鹵素原子、氰基、取代或無取代之碳數1~20之烷基、取代或無取代之甲矽烷基(silyl)、或取代或無取代之形成環之 碳數6~30之芳香族烴基,Ar21~Ar24各自表示取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基,Ar21~Ar24具有烷基作為取代基時,各自至少具有2個以上之烷基]。 An organic electroluminescence device comprising: a cathode; an anode; and an organic layer disposed between the cathode and the anode and containing at least one or more of the light-emitting layers; and the light-emitting layer is represented by the following general formula (1) And the derivative thereof is represented by the following general formula (21) derivative, [In the above general formula (1), any of R 1 ~ R 10 c departments for bonded to L 1 is a single bond, is not used to L 1 bonded to R 1 ~ R 10 are each selected from a hydrogen atom , halogen atom, hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted The aryloxy group having 6 to 30 carbon atoms forming a ring, the substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms forming a ring, Or a substituted or unsubstituted heterocyclic group having 5 to 30 atomic number of the ring forming ring, and L 1 is selected from any one of a single bond or a linking group, and the number of carbon atoms forming the ring in which the above linking group is substituted or unsubstituted 6 to 30 (a+1) of an aromatic hydrocarbon group, a substituted or unsubstituted ring-forming atomic group having 5 to 30 (a+1)-valent heterocyclic group, or the aforementioned substituted or unsubstituted ring forming ring An aromatic hydrocarbon group having 6 to 30 carbon atoms and a (a+1)-valent group formed by the bonding of 2 to 4 groups selected from the above-mentioned substituted or unsubstituted heterocyclic group having 5 to 30 atomic groups forming a ring, a, b, c each represent an integer of 1 to 4, Z 1 following a line Represented by the formula (2)] [In the above general formula (2), X 1 is selected from any one of an oxygen atom or a sulfur atom, and each of R 111 to R 118 is not used in the above general formula (1), and is not used for R 1 bonded to L 1 . R 10 is synonymous, but R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , R 115 and R 116 , R 116 and R 117 or 2 of R 117 and R 118 are adjacent to each other. a substituent, which is bonded to each other to form a ring represented by the following general formula (3) or (4)] [In the above general formula (3), y 1 and y 2 represent a bonding position selected from R 111 to R 118 of the above general formula (2), and in the above general formula (4), y 3 and y 4 are selected from the group consisting of y 3 and y 4 . The bonding positions of R 111 to R 118 of the above general formula (2), R 121 to R 124 and R 125 to R 128 are each not in the above general formula (1), and are not used for R 1 bonding with L 1 . R 10 is synonymous, and X 2 is selected from any one of an oxygen atom or a sulfur atom. In the above general formula (2), R 111 to R 118 which does not form a ring, and R 121 to R 124 of the above general formula (3) In one or the above general formula (2), any of R 111 to R 118 which does not form a ring, and R 125 to R 128 of the above general formula (4) are single bonds, and are used for L of the above general formula (1). 1 bond knot] [In the above general formula (21), R 20 to R 29 are each represented by a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted methyroalkyl group (silyl). Or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and Ar 21 to Ar 24 each represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms forming a ring, or a substituted or a The heterocyclic group having 5 to 30 atoms in the form of a ring is substituted, and when Ar 21 to Ar 24 have an alkyl group as a substituent, each has at least two or more alkyl groups]. 一種有機電致發光元件,其特徵係具有陰極;陽極;配置於前述陰極與前述陽極之間,至少含有發光層之1層以上的有機層;前述發光層為含有以下述一般式(1)表示之蒽衍生物與以下述一般式(41)表示之芘衍生物, [前述一般式(1)中,R1~R10之任意c個係用於與L1鍵結的單鍵,未用於與L1鍵結的R1~R10各自為選自氫原子、鹵素原子、羥基、氰基、取代或無取代之胺基、取代或無取代之碳數1~20之烷基、取代或無取代之碳數1~20之烷氧基、取代或無取代之形成環之碳數6~30之芳氧基、 取代或無取代之形成環之碳數6~30之芳硫基、取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基之任一,L1係選自單鍵或連結基之任一,前述連結基係取代或無取代之形成環之碳數6~30之(a+1)價之芳香族烴基、取代或無取代之形成環之原子數5~30之(a+1)價之雜環基、或前述取代或無取代之形成環之碳數6~30之芳香族烴基及前述取代或無取代之形成環之原子數5~30之雜環基所選出之基團2~4個鍵結形成之(a+1)價基團,a、b、c各自表示1~4之整數,Z1係以下述一般式(2)表示] [前述一般式(2)中,X1係選自氧原子或硫原子之任一,R111~R118各自與前述一般式(1)中,未用於與L1鍵結的R1~R10同義,但是R111與R112、R112與R113、R113與R114、R115與R116、R116與R117或R117與R118之中至少1組之鄰接的2 個取代基,互相鍵結形成以下述一般式(3)或(4)表示之環] [前述一般式(3)中,y1、y2表示選自前述一般式(2)之R111~R118的鍵結位置,前述一般式(4)中,y3、y4表示選自前述一般式(2)之R111~R118的鍵結位置,R121~R124、R125~R128各自與前述一般式(1)中,未用於與L1鍵結之R1~R10同義,X2係選自氧原子或硫原子之任一,前述一般式(2)中,未形成環之R111~R118及前述一般式(3)之R121~R124之任一個或前述一般式(2)中,未形成環之R111~R118及前述一般式(4)之R125~R128之任一個為單鍵,用於與前述一般式(1)之L1鍵結] [前述一般式(41)中,R21~R28各自表示為氫原子、鹵素原 子、氰基、取代或無取代之碳數1~20之烷基、取代或無取代之甲矽烷基(silyl)、或取代或無取代之形成環之碳數6~30之芳香族烴基,Ar21~Ar24各自表示取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基,但是前述一般式(41)中,Ar21~Ar24之中,至少1個為以下述式(42)表示之雜環基] [前述一般式(42)中,R211~R217各自表示氫原子、鹵素原子、氰基、取代或無取代之碳數1~20之烷基、取代或無取代之碳數2~20之烯基、取代或無取代之碳數2~20之炔基、取代或無取代甲矽烷基、取代或無取代之形成環之碳數6~30之芳香族烴基或取代或無取代之形成環之原子數5~30之雜環基,又,R211與R212、R212與R213、R213與R214、R215與R216、及R216與R217彼此鍵結可形成飽和或不飽和的環,此等之環可被取代,X21係選自氧原子或硫原子之任一, y21係與前述一般式(41)之氮原子鍵結的單鍵]。 An organic electroluminescence device comprising: a cathode; an anode; and an organic layer disposed between the cathode and the anode and containing at least one or more of the light-emitting layers; and the light-emitting layer is represented by the following general formula (1) a hydrazine derivative and an anthracene derivative represented by the following general formula (41), [In the above general formula (1), any of R 1 ~ R 10 c departments for bonded to L 1 is a single bond, is not used to L 1 bonded to R 1 ~ R 10 are each selected from a hydrogen atom , halogen atom, hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted The aryloxy group having 6 to 30 carbon atoms forming a ring, the substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms forming a ring, Or a substituted or unsubstituted heterocyclic group having 5 to 30 atomic number of the ring forming ring, and L 1 is selected from any one of a single bond or a linking group, and the number of carbon atoms forming the ring in which the above linking group is substituted or unsubstituted 6 to 30 (a+1) of an aromatic hydrocarbon group, a substituted or unsubstituted ring-forming atomic group having 5 to 30 (a+1)-valent heterocyclic group, or the aforementioned substituted or unsubstituted ring forming ring An aromatic hydrocarbon group having 6 to 30 carbon atoms and a (a+1)-valent group formed by the bonding of 2 to 4 groups selected from the above-mentioned substituted or unsubstituted heterocyclic group having 5 to 30 atomic groups forming a ring, a, b, and c each represent an integer from 1 to 4, and Z 1 is one of the following General expression (2) means] [In the above general formula (2), X 1 is selected from any one of an oxygen atom or a sulfur atom, and each of R 111 to R 118 is not used in the above general formula (1), and is not used for R 1 bonded to L 1 . R 10 is synonymous, but R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , R 115 and R 116 , R 116 and R 117 or 2 adjacent to at least one of R 117 and R 118 a substituent, which is bonded to each other to form a ring represented by the following general formula (3) or (4)] [In the above general formula (3), y 1 and y 2 represent a bonding position selected from R 111 to R 118 of the above general formula (2), and in the above general formula (4), y 3 and y 4 are selected from the group consisting of y 3 and y 4 . The bonding positions of R 111 to R 118 of the above general formula (2), R 121 to R 124 and R 125 to R 128 are each not in the above general formula (1), and are not used for R 1 bonding with L 1 . R 10 is synonymous, and X 2 is selected from any one of an oxygen atom or a sulfur atom. In the above general formula (2), R 111 to R 118 which does not form a ring, and R 121 to R 124 of the above general formula (3) In one or the above general formula (2), any of R 111 to R 118 which does not form a ring, and R 125 to R 128 of the above general formula (4) are single bonds, and are used for L of the above general formula (1). 1 bond knot] [In the above general formula (41), R 21 to R 28 are each represented by a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted methyroalkyl group (silyl). Or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and Ar 21 to Ar 24 each represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms forming a ring, or a substituted or a In the above general formula (41), at least one of Ar 21 to Ar 24 is a heterocyclic group represented by the following formula (42), which is substituted with a heterocyclic group having 5 to 30 atoms. [In the above general formula (42), R 211 to R 217 each represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted carbon number of 2 to 20; Alkenyl, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted metaalkyl group, substituted or unsubstituted ring-forming aromatic hydrocarbon group having 6 to 30 carbon atoms or substituted or unsubstituted ring forming ring a heterocyclic group having 5 to 30 atoms, and R 211 and R 212 , R 212 and R 213 , R 213 and R 214 , R 215 and R 216 , and R 216 and R 217 may be bonded to each other to form a saturated or An unsaturated ring, such a ring may be substituted, and X 21 is selected from any one of an oxygen atom or a sulfur atom, and y 21 is a single bond bonded to the nitrogen atom of the above general formula (41)]. 如申請專利範圍第1或2項之有機電致發光元件,其中前述一般式(1)中之Z1為以下述一般式(5)~(7)之任一表示者, [前述一般式(5)~(7)中,R131~R140、R141~R150、R151~R160各自與前述一般式(1)中,未用於與L1鍵結之R1~R10同義,但是R131~R140之任一、R141~R150之任一、R151~R160之任一係用於與L1鍵結,而用於與L1鍵結之基團為單鍵,X1、X2各自與前述一般式(2)中之X1、前述一般式(4)中之X2同義,X1與X2係相同或相異]。 The organic electroluminescence device according to claim 1 or 2, wherein Z 1 in the above general formula (1) is represented by any one of the following general formulas (5) to (7), [In the above general formulas (5) to (7), R 131 to R 140 , R 141 to R 150 , and R 151 to R 160 are each not in the above general formula (1), and are not used for bonding to L 1 . 1 to R 10 are synonymous, but any of R 131 to R 140 , any of R 141 to R 150 , and any of R 151 to R 160 are used for bonding with L 1 and for bonding with L 1 the group is a single bond, X 1, X 2 are each the aforementioned general formula (2) in the X 1, the (4) in the same meaning as the general formula X 2, identical or different X 1 and X 2 Department]. 如申請專利範圍第1或2項之有機電致發光元件,其中前述一般式(1)中之Z1為以下述一般式(8)~(10)之任一表示者, [前述一般式(8)~(10)中,R161~R170、R171~R180、R181~R190各自與前述一般式(1)中,未用於與L1鍵結之R1~R10同義,但是R161~R170之任一、R171~R180之任一、R181~R190之任一係用於與L1鍵結,而用於與L1鍵結之基團為單鍵,X1係與前述一般式(2)中之X1同義]。 The organic electroluminescence device according to claim 1 or 2, wherein Z 1 in the above general formula (1) is represented by any one of the following general formulas (8) to (10), [In the above general formulas (8) to (10), R 161 to R 170 , R 171 to R 180 , and R 181 to R 190 each are the same as those in the above general formula (1), which are not used for bonding with L 1 . 1 to R 10 are synonymous, but any of R 161 to R 170 , any of R 171 to R 180 , and any of R 181 to R 190 are used for bonding with L 1 and for bonding with L 1 The group is a single bond, and the X 1 system is synonymous with X 1 in the above general formula (2)]. 如申請專利範圍第1或2項之有機電致發光元件,其中前述一般式(1)之b為1。 An organic electroluminescence device according to claim 1 or 2, wherein b of the above general formula (1) is 1. 如申請專利範圍第1或2項之有機電致發光元件, 其中前述一般式(1)之a為1或2。 For example, the organic electroluminescent element of claim 1 or 2, Wherein a of the above general formula (1) is 1 or 2. 如申請專利範圍第1或2項之有機電致發光元件,其中前述一般式(1)之R9及R10之至少任一為用於與L1鍵結的單鍵。 The organic electroluminescence device according to claim 1 or 2, wherein at least one of R 9 and R 10 of the above general formula (1) is a single bond for bonding with L 1 . 如申請專利範圍第1或2項之有機電致發光元件,其中前述一般式(1)之R9為選自取代或無取代之形成環之碳數6~30之芳香族烴基、或取代或無取代之形成環之原子數5~30之雜環基之基團。 The organic electroluminescent device according to claim 1 or 2, wherein R 9 of the above general formula (1) is an aromatic hydrocarbon group selected from a substituted or unsubstituted ring-forming carbon number of 6 to 30, or substituted or An unsubstituted group forming a heterocyclic group having 5 to 30 atomic number of the ring. 如申請專利範圍第1或2項之有機電致發光元件,其中X1及X2為氧原子。 An organic electroluminescence device according to claim 1 or 2, wherein X 1 and X 2 are oxygen atoms. 如申請專利範圍第3項之有機電致發光元件,其中前述一般式(8)~(10)中,R161~R164之任一、R171~R174之任一、R181~R184之任一為用於與L1鍵結,且用於與L1鍵結的基團為單鍵。 An organic electroluminescence device according to claim 3, wherein in the general formulas (8) to (10), any one of R 161 to R 164 , any of R 171 to R 174 , and R 181 to R 184 Either one for bonding with L 1 and a group for bonding with L 1 is a single bond. 如申請專利範圍第10項之有機電致發光元件,其中前述一般式(1)表示之蒽衍生物係以下述一般式(15)~(20)之任一表示, [前述一般式(15)~(20)中之R161~R190各自與前述一般式(1)中之R1~R8同義,前述一般式(15)~(20)中之X1係與前述一般式(2)中之X1同義]。 The organic electroluminescence device according to claim 10, wherein the anthracene derivative represented by the above general formula (1) is represented by any one of the following general formulas (15) to (20). [R 161 to R 190 in the above general formulas (15) to (20) are each synonymous with R 1 to R 8 in the above general formula ( 1 ), and the X 1 series in the above general formulas (15) to (20) It is synonymous with X 1 in the above general formula (2)]. 如申請專利範圍第10項之有機電致發光元件,其中前述一般式(1)表示之蒽衍生物係以下述一般式(51)~(56)之任一表示者, [前述一般式(51)~(56)中之R161~R190係與前述一般式(1)中之R1~R8同義,前述一般式(51)~(56)中之X1係與前述一般式(2)中之X1同義]。 The organic electroluminescence device according to claim 10, wherein the anthracene derivative represented by the above general formula (1) is represented by any one of the following general formulas (51) to (56). [R 161 to R 190 in the above general formulas (51) to (56) are synonymous with R 1 to R 8 in the above general formula ( 1 ), and the X 1 series in the above general formulas (51) to (56) It is synonymous with X 1 in the above general formula (2)]. 如申請專利範圍第10項之有機電致發光元件,其中前述一般式(1)表示之蒽衍生物係以下述一般式(57)~(62)之任一表示, [前述一般式(57)~(62)中之R161~R190係與前述一般式(1)中之R1~R8同義,前述一般式(57)~(62)中之X1係與前述一般式(2)中之X1同義]。 The organic electroluminescence device according to claim 10, wherein the anthracene derivative represented by the above general formula (1) is represented by any one of the following general formulas (57) to (62). [R 161 to R 190 in the above general formulas (57) to (62) are synonymous with R 1 to R 8 in the above general formula ( 1 ), and the X 1 series in the above general formulas (57) to (62) It is synonymous with X 1 in the above general formula (2)]. 如申請專利範圍第1項之有機電致發光元件,其中前述一般式(21)之R20~R29為氫原子。 The organic electroluminescence device according to claim 1, wherein R 20 to R 29 of the above general formula (21) are a hydrogen atom. 如申請專利範圍第2項之有機電致發光元件,其中前述一般式(41)之Ar21及Ar23為前述一般式(42)表示之雜環基。 The organic electroluminescence device according to claim 2, wherein Ar 21 and Ar 23 of the above general formula (41) are a heterocyclic group represented by the above general formula (42). 如申請專利範圍第2項之有機電致發光元件,其中前述一般式(41)之R21~R28為氫原子。 The organic electroluminescence device according to claim 2, wherein R 21 to R 28 of the above general formula (41) are a hydrogen atom. 如申請專利範圍第2項之有機電致發光元件,其 中前述一般式(41)之R22及R26為取代或無取代之碳數1~20之烷基、或取代或無取代之碳數3~30之烷基甲矽烷基,前述一般式(41)之R21、R23、R24、R25、R27、及R28為氫原子。 The organic electroluminescent device of claim 2, wherein R 22 and R 26 of the above general formula (41) are a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted carbon number. The alkylmercaptoalkyl group of 3 to 30, wherein R 21 , R 23 , R 24 , R 25 , R 27 and R 28 of the above general formula (41) are a hydrogen atom. 如申請專利範圍第2項之有機電致發光元件,其中前述一般式(42)之X21為氧原子。 An organic electroluminescence device according to claim 2, wherein X 21 of the above general formula (42) is an oxygen atom.
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