KR20090086920A - Organoelectroluminescent device and a compound used in the device - Google Patents
Organoelectroluminescent device and a compound used in the device Download PDFInfo
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- KR20090086920A KR20090086920A KR1020090011010A KR20090011010A KR20090086920A KR 20090086920 A KR20090086920 A KR 20090086920A KR 1020090011010 A KR1020090011010 A KR 1020090011010A KR 20090011010 A KR20090011010 A KR 20090011010A KR 20090086920 A KR20090086920 A KR 20090086920A
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- 150000001875 compounds Chemical class 0.000 title claims description 33
- 238000002347 injection Methods 0.000 claims abstract description 32
- 239000007924 injection Substances 0.000 claims abstract description 32
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 10
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- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
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- 125000000524 functional group Chemical group 0.000 claims description 3
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
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Abstract
Description
본 발명은 유기전계발광소자 및 이에 사용되는 화합물에 관한 것으로서, 더욱 구체적으로 전력효율 및 발광효율이 우수하며, 장수명을 갖는 유기전계발광소자 및 이에 사용되는 화합물에 관한 것이다.The present invention relates to an organic electroluminescent device and a compound used therein, and more particularly, to an organic electroluminescent device having excellent power efficiency and luminous efficiency, and having a long life, and a compound used therein.
유기전계발광소자 (이하, 유기 EL 소자라 함)는 정공주입전극인 제1 전극 (애노드 전극)과 전자주입전극인 제2 전극 (캐소드 전극) 사이에 형성된 형광성 또는 인광성 유기 화합물 박막 (이하, 유기막이라고 함)에 전자 및 정공을 주입하면, 전자와 정공이 결합하여 쌍을 이룸으로써 생성된 엑시톤 (exciton)이 여기 상태로부터 기저 상태로 떨어지면서 소멸하여 발광하는 원리를 이용한 능동 발광형 표시 소자로서, 경량화가 가능하며, 부품이 간소하여 제작공정이 간단하고, 응답속도가 빠르며, 고화질의 넓은 시야각을 확보하고 있다는 등의 장점들을 갖는다. 또한, 동영상을 완벽하게 구현할 수 있고, 고색순도 구현이 가능하며, 초박형화 및 초경량화가 가능하고, 소비 전력 및 구동전압이 낮아서 휴대용 전자기기에 적합한 전기적 특성을 갖고 있다.An organic electroluminescent device (hereinafter referred to as an organic EL device) is a fluorescent or phosphorescent organic compound thin film formed between a first electrode (anode electrode) which is a hole injection electrode and a second electrode (cathode electrode) which is an electron injection electrode (hereinafter, When the electrons and holes are injected into the organic layer, the excitons generated by the combination of electrons and holes are paired to fall from the excited state to the ground state. As a result, it is possible to reduce the weight, and the components are simple, so that the manufacturing process is simple, the response speed is fast, and the wide viewing angle of high quality is secured. In addition, video can be fully realized, high color purity can be realized, ultra-thin and ultra-light, and power consumption and driving voltage are low, which makes it suitable for portable electronic devices.
초창기의 대표적 유기전계발광소자는 1969년 구르니 (Gurnee)에 의해서 공지된 단층구조의 것으로서 (미국등록특허 제3,172,862호 및 미국등록특허 제3,173,050호), 100V 이상의 과도한 구동전압을 필요로 하기 때문에 실용화되기 어렵다는 문제점이 있었다. 따라서, 이러한 문제점을 해결하고자, 1987년 이스트만 코닥사 (Eastman Kodak co.)의 Tang에 의해 약 6 내지 14V 정도의 현저히 낮은 구동전압을 갖는 다층구조의 유기전계발광소자가 개발되었으며 (C. W. Tang et al., Appl. Phys. Lett., 51, 913(1987); J. Applied Phys., 65, 3610(1989); US4,356,429), 현재는 정공주입층, 정공수송층, 전자수송층 및 전자주입층 등과 같은 다양한 기능성 적층구조들을 갖는 유기전계발광소자들이 지속적으로 개발되고 있는 추세이다.Representative organic electroluminescent devices of the early days have a single layer structure known by Gurnee in 1969 (US Patent No. 3,172,862 and US Patent No. 3,173,050), and are practically used because they require excessive driving voltage of 100 V or more. There was a problem that it is difficult to be. Therefore, in order to solve this problem, a multi-layered organic electroluminescent device having a significantly low driving voltage of about 6 to 14 V was developed by Tang of Eastman Kodak Co. in 1987 (CW Tang et al. ., Appl. Phys. Lett ., 51, 913 (1987); J. Applied Phys ., 65, 3610 (1989); US 4,356, 429), currently a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer, etc. Organic electroluminescent devices having the same various functional stacking structures are continuously being developed.
한편, 종래의 유기전계발광소자에는 안트라센 및 그 유도체가 다양한 용도로 채용된 바 있는데, "ADN"이라는 약어로 잘 알려진 9,10-디(2-나프틸)안트라센 (미국등록특허 제5,935,721호), 9-나프틸-10-페닐안트라센 유도체 (미국공개특허공보 제2006/0014046호) 및 9-비페닐-10-나프틸안트라센 유도체 (국제특허공개공보 제2005/080527호) 등은 발광층의 호스트로서 사용된 바 있고, 비스-안트라센을 발광층으로 사용하여 유기전계발광소자의 수명을 개선시킨 기술도 개시된 바 있다 (미국등록특허 제6,534,199호). 또한, 정공수송층 (HTL)에 안트라센 유도체를 채용한 기술도 개시된 바 있으며 (미국등록특허 제6,465,115호 및 미국등록특허 제5,759,444호), 그 밖에도 다양한 용도로 안트라센 및 그 유도체가 유기전계발광소자에 채용된 바 있다.On the other hand, anthracene and its derivatives have been employed in various conventional organic electroluminescent devices, and 9,10-di (2-naphthyl) anthracene, which is well known as an abbreviation of "ADN" (US Patent No. 5,935,721). , 9-naphthyl-10-phenylanthracene derivatives (US Patent Publication No. 2006/0014046) and 9-biphenyl-10-naphthylanthracene derivatives (International Patent Publication No. 2005/080527) and the like are hosts of the light emitting layer. As a light emitting layer, bis-anthracene has been used as a light emitting layer to improve the lifespan of an organic light emitting display device (US Pat. No. 6,534,199). In addition, a technique using an anthracene derivative in the hole transport layer (HTL) has also been disclosed (US Pat. No. 6,465,115 and US Pat. No. 5,759,444), and anthracene and its derivatives are employed in organic electroluminescent devices for various purposes. It has been.
상술한 바와 같이, 유기전계발광소자에 안트라센을 채용한 많은 연구가 이루어지고 있지만, 현재까지는 요구되는 휘도, 효율, 구동 안정성 및 수명 등의 특성을 충분히 만족시키지 못하고 있는 실정이며, 따라서 이를 해결하기 위한 다양한 기술개발이 시급한 실정이다. 특히, 발광층 호스트 (host)에 도펀트 (dopant)를 도핑하는 에너지 이동 원리를 기본으로 하는 호스트-게스트 시스템에 있어서, 발광층 호스트 물질로서 새로운 안트라센 유도체에 대한 많은 연구가 필요한 상황이다.As described above, many studies have been made in which anthracene is employed in the organic light emitting display device, but until now, the present conditions have not sufficiently satisfied characteristics such as brightness, efficiency, driving stability, and lifespan. Various technological developments are urgently needed. In particular, in a host-guest system based on the principle of energy transfer in which a dopant is doped to a light emitting layer host, a lot of research on a new anthracene derivative as a light emitting layer host material is required.
본 발명이 해결하고자 하는 첫 번째 과제는 전력효율 및 발광효율이 우수하며, 장수명을 갖는 유기전계발광소자를 제공하는 것이다.The first problem to be solved by the present invention is to provide an organic light emitting device having excellent power efficiency and luminous efficiency, and has a long life.
또한 본 발명이 해결하고자 하는 두 번째 과제는 상기 유기전계발광소자에 사용할 수 있는 신규한 화합물을 제공하는 것이다.In addition, a second problem to be solved by the present invention is to provide a novel compound that can be used in the organic light emitting device.
상기 첫 번째 기술적 과제를 달성하기 위해서, 본 발명은 애노드; 캐소드; 및 상기 애노드와 캐소드 사이에 하기 식 1로 표시되는 화합물을 포함하는 층을 구비한 유기전계발광소자를 제공한다:In order to achieve the first technical problem, the present invention is an anode; Cathode; And a layer comprising a compound represented by
(1) (One)
(상기 식에서, X1 내지 X5 은 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 24의 알킬기, 치환 또는 비치환된 탄소수 1 내지 24의 헤테로 알킬기, 치환 또는 비치환된 탄소수 1 내지 24의 사이클로알킬기, 치환 또는 비치환된 탄소수 1 내지 24의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 24의 시아노기, 치환 또는 비치환된 탄소수 1 내지 24의 할로겐기, 치환 또는 비치환된 탄소수 1 내지 24의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 24의 실릴기, 중수소 및 수소로 이루어진 군으로부터 선택되며, 단, X1~X5 모두 수소일 경우 안트라센의 3, 7 위치의 R은 반드시 수소이고, Wherein X 1 to X 5 each independently represent a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted hetero alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 24 carbon atoms A substituted or unsubstituted alkoxy group having 1 to 24 carbon atoms, a substituted or unsubstituted cyano group having 1 to 24 carbon atoms, a substituted or unsubstituted halogen group having 1 to 24 carbon atoms, a substituted or unsubstituted carbon group having 1 to 24 carbon atoms An aryloxy group, a substituted or unsubstituted silyl group having 1 to 24 carbon atoms, deuterium, and hydrogen, provided that when X 1 to X 5 are both hydrogen, R in the 3 and 7 positions of anthracene is hydrogen; ,
R은 치환 또는 비치환된 탄소수 6 내지 20의 아릴기 또는 치환 또는 비치환된 탄소수 3 내지 19의 헤테로아릴기 및 수소로 이루어진 군으로부터 선택되며, 단, 3개 이상이 동시에 수소는 아니고,R is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 19 carbon atoms and hydrogen, provided that at least three are not hydrogen at the same time,
상기 X1 내지 X5 및 R이 치환된 작용기일 경우의 치환기는 탄소수 1 내지 10의 알킬기, 탄소수 4 내지 7의 사이클로알킬기, 탄소수 1 내지 10의 알콕시기, 시아노기, 탄소수 1 내지 10의 알킬실릴기, 할로겐기, 탄소수 6 내지 20의 아릴기, 탄소수 6 내지 10의 아릴옥시기, 탄소수 6 내지 18의 아릴실릴기, 탄소수 3 내지 19의 헤테로아릴기, 중수소 및 수소로 이루어진 군으로부터 선택된다.)In the case where X 1 to X 5 and R are substituted functional groups, the substituent is an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 4 to 7 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cyano group, and an alkylsilyl having 1 to 10 carbon atoms. It is selected from the group consisting of a group, a halogen group, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylsilyl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 19 carbon atoms, deuterium and hydrogen. )
본 발명의 일실시예에 따르면, 상기 유기전계발광소자에서 상기 애노드와 캐소드 사이에 개재된 층에 포함된 화합물은 하기 식 (2) 내지 (80)으로 표시되는 군으로부터 선택된 어느 하나일 수 있다. According to an embodiment of the present invention, the compound included in the layer interposed between the anode and the cathode in the organic light emitting device may be any one selected from the group represented by the following formula (2) to (80).
(2) (3) (2) (3)
(4) (5) (4) (5)
(6) (7) (6) (7)
(8) (9) (8) (9)
(10) (11) (10) (11)
(12) (13) (12) (13)
(14) (15) (14) (15)
(16) (17) (16) (17)
(18) (19) (18) (19)
(20) (21) (20) (21)
(22) (23) (22) (23)
(24) (25) (24) (25)
(26) (27) (26) (27)
(28) (29) (28) (29)
(30) (31) (30) (31)
(32) (33) (32) (33)
(34) (35) (34) (35)
(36) (37) (36) (37)
(38) (39) (38) (39)
(40) (41) (40) (41)
(42) (43) (42) (43)
(44) (45) (44) (45)
(46) (47) (46) (47)
(48) (49) (48) (49)
(50) (51) (50) (51)
(52) (53) (52) (53)
(54) (55) (54) (55)
(56) (57) (56) (57)
(58) (59) (58) (59)
(60) (61) (60) (61)
(62) (63) (62) (63)
(64) (65) (64) (65)
(66) (67) (66) (67)
(68) (69) (68) (69)
(70) (71) (70) (71)
(72) (73) (72) (73)
(74) (75) (74) (75)
(76) (77) (76) (77)
(78) (79) (78) (79)
(80) (80)
본 발명은 두 번째 과제를 해결하기 위하여, 유기전계발광소자에 사용하는 것을 특징으로 하는 상기 화학식 (1)로 표시되는 화합물을 제공한다. The present invention provides a compound represented by the formula (1) characterized in that it is used in an organic electroluminescent device in order to solve the second problem.
본 발명의 일실시예에 따르면, 상기 화학식 (1)로 표시되는 화합물은 상기 식 (2) 내지 (80)으로 표시되는 화합물로 이루어진 군으로부터 선택될 수 있다. According to one embodiment of the present invention, the compound represented by the formula (1) may be selected from the group consisting of the compound represented by the formula (2) to (80).
본 발명에 따르면, 전력효율 및 발광효율이 우수하며, 장수명을 갖는 유기전계발광소자를 제공할 수 있다.According to the present invention, it is possible to provide an organic light emitting device having excellent power efficiency and luminous efficiency and having a long lifespan.
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 종래 발광층 호스트 물질 등에 폭넓게 사용되고 있는 안트라센 유도체의 휘도, 효율, 구동 안정성 및 수명 등의 특성을 개선하기 위한 것이며, 특히 상기 화학식 (1)로 표시되는 구조를 갖는 안트라센 유도체가 뛰어난 전력효율, 발 광효율 및 수명특성을 갖는다는 점에 착안하여 완성된 것이다.The present invention is to improve the characteristics such as brightness, efficiency, driving stability and lifespan of anthracene derivatives widely used in conventional light emitting layer host materials and the like, in particular, the anthracene derivative having the structure represented by the formula (1) has excellent power efficiency, It is completed by paying attention to the light emitting efficiency and lifespan.
본 발명에 따른 안트라센 유도체는 안트라센을 기본골격으로 하여 9번 및 10번 탄소의 치환기를 치환된 페닐기로 고정한 구조이며 상기 페닐기의 역할로 인해 분자의 벌크상에서의 트위스팅이 적절히 조절되어 분자간의 스택킹이 향상되고 이로 인해 p-p 스택킹(p-p stacking)이 향상되어 수명특성 및 효율이 향상되는 것으로 판단된다. 한편, 상기 치환기로써 알킬, 알킬실릴, 알콕시 등의 전자공여기를 사용함으로써 소자의 수명 및 효율을 향상시킬 수 있으며, 상기 치환기로서 시아노기 또는 할로겐을 사용하는 경우에는 결정성을 향상시키기 때문에 분자간의 스택킹이 우수하게 되어 벌크 특성이 향상되는 것으로 예상할 수 있다.The anthracene derivative according to the present invention has a structure in which anthracene is a basic skeleton and substituents of carbons 9 and 10 are fixed with a substituted phenyl group, and due to the role of the phenyl group, the twisting on the bulk of the molecule is appropriately controlled to stack between molecules. This improves the pp stacking (pp stacking) it is believed to improve the life characteristics and efficiency. On the other hand, the lifetime and efficiency of the device can be improved by using electron donating groups such as alkyl, alkylsilyl and alkoxy as the substituent, and in the case of using a cyano group or halogen as the substituent, the intermolecular stack is improved. It can be expected that the king will be superior and the bulk properties will be improved.
상술한 바와 같은 구조를 갖는 화학식 (1)에 따른 안트라센 유도체에 대한 구체적인 예들로는, 이에 제한되는 것은 아니지만, 상기 화학식 (2) 내지 화학식 (80)으로 표시되는 군으로부터 선택된 어느 하나의 화합물을 예로 들 수 있다:Specific examples of the anthracene derivative according to Formula (1) having the structure as described above include, but are not limited to, any one compound selected from the group represented by Formulas (2) to (80) above Can:
본 발명에 따른 유기전계발광소자는 상기 애노드 및 캐소드 사이에 정공주입층, 정공수송층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 어느 하나 이상의 층을 더 포함할 수도 있는데, 상기 정공주입층, 정공수송층, 전자수송층 및 전자주입층은 정공 또는 전자들을 효율적으로 전달시켜 줌으로써 발광 결합의 확률을 높이는 역할을 한다.The organic light emitting device according to the present invention may further include any one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer between the anode and the cathode, the hole injection layer, holes The transport layer, the electron transport layer, and the electron injection layer serve to increase the probability of light emitting coupling by efficiently transferring holes or electrons.
정공주입층 및 정공수송층은 애노드로부터 정공이 주입되고, 주입된 정공이 수송되는 것을 용이하게 하기 위해서 적층되는 것으로서, 이러한 정공수송층용 물질로는 이온화 포텐셜이 작은 전자공여성 분자들이 사용되는데, 주로 트리페닐아민 을 기본골격으로 하는 디아민, 트리아민 또는 테트라아민 유도체가 많이 사용되고 있다. 본 발명에서도, 상기 정공수송층의 재료로서, 당업계에 통상적으로 사용되는 것인 한, 다양한 물질을 제한 없이 사용할 수 있으며, 예를 들어, N,N'-비스(3-메틸페닐)-N,N'-디페닐-[1,1-비페닐]-4,4'-디아민(TPD) 또는 N,N'-디(나프탈렌-1-일)- N,N'-디페닐 벤지딘(a-NPD) 등을 사용할 수 있다. 또한, 상기 정공수송층의 하부에는 정공주입층 (HIL: Hole Injecting Layer)을 추가적으로 더 적층할 수 있는데, 상기 정공주입층 재료 역시 당업계에서 통상적으로 사용되는 것인 한 특별히 제한되지 않고 사용할 수 있으며, 예를 들어 하기 화학식 81 내지 83에 열거된 CuPc (화학식 81) 또는 스타버스트(Starburst)형 아민류인 TCTA (화학식 82), m-MTDATA (화학식 83) 등을 사용할 수 있으며, 이 이외에 IDE406 (이데미쯔사 재료) 등도 사용할 수 있다.The hole injection layer and the hole transport layer are laminated to facilitate the injection of holes from the anode and the transport of the injected holes. As the material for the hole transport layer, electron donor molecules having small ionization potential are used. Diamine, triamine or tetraamine derivatives based on amines are frequently used. In the present invention, as the material of the hole transport layer, as long as it is commonly used in the art, various materials can be used without limitation, for example, N, N'-bis (3-methylphenyl) -N, N '-Diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (a-NPD ) Can be used. In addition, a hole injection layer (HIL) may be further stacked below the hole transport layer, and the hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. For example, CuPc (Chemical Formula 81) or Starburst type amines listed in Chemical Formulas 81 to 83, TCTA (Chemical Formula 82), m-MTDATA (Chemical Formula 83), and the like may be used. In addition, IDE406 (Idemitsu) Yarn material) and the like.
(81) (81)
(82) (82)
(83) (83)
한편, 상기 전자수송층은 캐소드로부터 공급된 전자를 발광층으로 원활히 수송하고 상기 발광층에서 결합하지 못한 정공의 이동을 억제함으로써 발광층 내에서 재결합할 수 있는 기회를 증가시키는 역할을 한다. 이러한 전자수송층 재료로는 당업계에서 사용되는 물질인 한 특별히 제한되지 않으며, 예를 들어, 8-히드록시 퀴놀린 알루미늄 (Alq3), 2-(4-비페닐일)-5-(4-t-부틸페닐)-1,3,4-옥사디아졸 (PBD), 2,4,7-트리니트로 플루오레논 (TNF), 또는 하기 [화학식 84, 85]의 BMD, BND 등을 사용할 수 있다.On the other hand, the electron transport layer serves to increase the chance of recombination in the light emitting layer by smoothly transporting the electrons supplied from the cathode to the light emitting layer and suppressing the movement of holes that are not bonded in the light emitting layer. Such electron transport layer material is not particularly limited as long as it is a material used in the art, for example, 8-hydroxy quinoline aluminum (Alq 3 ), 2- (4-biphenylyl) -5- (4-t -Butylphenyl) -1,3,4-oxadiazole (PBD), 2,4,7-trinitro fluorenone (TNF), or BMD, BND, etc. of the following formulas (84, 85) can be used.
(84) (85) (84) (85)
BMD BND BMD BND
한편, 상기 전자수송층의 상부에는 캐소드로부터의 전자 주입을 용이하게 해주어 궁극적으로 파워효율을 개선시키는 기능을 수행하는 전자주입층 (EIL: Electron Injecting Layer)을 더 적층시킬 수도 있는데, 상기 전자주입층 재료 역시 당업계에서 통상적으로 사용되는 것이면 특별한 제한 없이 사용될 수 있으며, 예를 들어, LiF, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다.Meanwhile, an electron injection layer (EIL) may be further stacked on the upper portion of the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. Also commonly used in the art may be used without particular limitation, for example, it may be used a material such as LiF, NaCl, CsF, Li 2 O, BaO.
더 나아가, 본 발명에 따른 유기전계발광소자는 상기 언급한 정공주입층, 정공수송층, 전자수송층 및 전자주입층 이외에도, 정공저지층 또는 전자저지층 등과 같은 부가적 기능성 적층 구조들을 더 포함할 수도 있다. 이때, 정공저지층은 정공이 유기발광층을 통과하여 캐소드로 유입되는 경우에는 소자의 수명과 효율이 감소되기 때문에 HOMO 레벨이 매우 낮은 물질을 사용함으로써 이러한 문제를 방지하는 역할을 한다. 정공저지층을 이루는 물질은 특별히 제한되지는 않으나, 전자수송능 력을 가지면서 발광 화합물보다 높은 이온화 포텐셜을 가져야 하며, 대표적으로 BAlq, BCP, TPBI 등을 사용할 수 있다. Furthermore, in addition to the above-described hole injection layer, hole transport layer, electron transport layer, and electron injection layer, the organic light emitting device according to the present invention may further include additional functional laminated structures such as a hole blocking layer or an electron blocking layer. . At this time, the hole blocking layer serves to prevent such a problem by using a material having a very low HOMO level because the life and efficiency of the device is reduced when holes are introduced into the cathode through the organic light emitting layer. The material constituting the hole blocking layer is not particularly limited, but must have an ionization potential higher than that of the light emitting compound while having an electron transport ability, and typically BAlq, BCP, TPBI, and the like may be used.
보다 구체적으로, 하기 도 1a 내지 도 1e에는 다양한 형태의 적층 구조를 갖는 유기전계발광소자들을 도시하였으며, 이를 참조하면, 도 1a의 유기전계발광소자는 애노드/정공주입층/발광층/캐소드로 이루어진 구조를 갖고, 도 1b의 유기전계발광소자는 애노드/정공주입층/발광층/전자주입층/캐소드로 이루어진 구조를 갖는다. 또한, 도 1c의 유기전계발광소자는 애노드/정공주입층/정공수송층/발광층/캐소드의 구조를 갖고, 도 1d에 도시된 유기전계발광소자는 애노드/정공주입층/정공수송층/발광층/전자주입층/캐소드의 구조를 갖는다. 마지막으로, 도 1e의 유기전계발광소자는 애노드/정공주입층/정공수송층/발광층/전자수송층/전자주입층/캐소드의 구조를 갖는다.More specifically, FIGS. 1A to 1E illustrate organic light emitting diodes having various types of stacked structures. Referring to this, the organic light emitting diode of FIG. 1A includes an anode / hole injection layer / light emitting layer / cathode. The organic electroluminescent device of FIG. 1B has a structure consisting of an anode / hole injection layer / light emitting layer / electron injection layer / cathode. In addition, the organic light emitting display device of FIG. 1c has a structure of an anode / hole injection layer / hole transporting layer / light emitting layer / cathode, and the organic light emitting device shown in FIG. 1d includes an anode / hole injection layer / hole transporting layer / light emitting layer / electron injection. Has a structure of layers / cathodes. Finally, the organic light emitting display device of FIG. 1E has a structure of an anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode.
한편, 본 발명에 따른 유기전계발광소자는 상기 안트라센 유도체를, 애노드 및 캐소드 사이에 개재되는 다양한 적층 구조 내에 포함할 수 있지만, 바람직하게는, 상기 안트라센 유도체는 애노드 및 캐소드 사이의 발광층 중에 포함되어, 발광층 호스트 물질로 채용될 수 있다.On the other hand, the organic electroluminescent device according to the present invention may include the anthracene derivative in a variety of laminated structures interposed between the anode and the cathode, preferably, the anthracene derivative is included in the light emitting layer between the anode and the cathode, It can be employed as the light emitting layer host material.
이하, 본 발명에 따른 유기전계발광소자를 제조하는 방법에 관하여 도 1a 내지 1e를 참조하여 설명한다. Hereinafter, a method of manufacturing an organic light emitting display device according to the present invention will be described with reference to FIGS. 1A to 1E.
먼저, 기판 상부에 애노드용 물질을 코팅한다. 기판으로는 통상적인 발광 소자에서 사용되는 기판을 사용하는데, 투명성, 표면 평활성, 취급용이성 및 방수성이 우수한 유리기판 또는 투명 플라스틱 기판이 바람직하다. 또한, 애노드 물질로 는 투명하고 전도성이 우수한 산화인듐주석 (ITO), 산화인듐아연 (IZO), 산화주석 (SnO2) 또는 산화아연 (ZnO) 등의 당업계에서 통상적으로 사용되고 있는 물질들이 사용될 수 있다. 상기 애노드 상부로는 정공주입층이 진공 열증착 또는 스핀코팅 등의 방법에 의해서 선택적으로 적층되며, 그 다음으로 상기 정공주입층 상부에 정공수송층을 진공 열증착 또는 스핀코팅 등의 방법에 의해서 형성된다.First, an anode material is coated on the substrate. As the substrate, a substrate used in a conventional light emitting device is used. A glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is preferable. In addition, as the anode material, materials commonly used in the art, such as transparent and highly conductive indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), or zinc oxide (ZnO), may be used. have. The hole injection layer is selectively stacked on the anode by vacuum thermal deposition or spin coating, and then the hole transport layer is formed on the hole injection layer by vacuum thermal deposition or spin coating. .
다음으로는, 상기 정공수송층 상부에 발광층을 적층한 후, 그 위에 선택적으로 정공저지층을 진공 열증착 또는 스핀코팅 방법에 의해서 형성한다. 마지막으로, 이러한 정공저지층 위에 전자수송층을 진공 열증착 또는 스핀코팅 방법을 통해 증착한 후에 전자주입층을 선택적으로 형성하고, 상기 전자주입층 상부에 캐소드 형성용 금속을 진공 열증착함으로써 본 발명에 따른 유기전계발광소자를 제조할 수 있게 된다. 한편, 캐소드 형성용 금속으로는, 리튬 (Li), 마그네슘 (Mg), 알루미늄 (Al), 알루미늄-리튬 (Al-Li), 칼슘 (Ca), 마그네슘-인듐 (Mg-In), 마그네슘-은 (Mg-Ag) 등을 사용할 수 있으며, 전면발광소자를 얻기 위해서는 ITO, IZO를 사용한 투과형 캐소드를 사용할 수도 있다.Next, after the light emitting layer is laminated on the hole transport layer, a hole blocking layer is selectively formed thereon by vacuum thermal evaporation or spin coating. Finally, the electron transport layer is deposited on the hole blocking layer by vacuum thermal deposition or spin coating, and then an electron injection layer is selectively formed, and the cathode forming metal is vacuum-deposited on the electron injection layer. The organic electroluminescent device according to the present invention can be manufactured. On the other hand, as the cathode forming metal, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) or the like, and a transmissive cathode using ITO or IZO may be used to obtain a front light emitting device.
이하, 본 발명을 하기 실시예를 통하여 본 발명을 보다 상세하게 설명하고자 하나, 하기의 실시예는 단지 설명의 목적을 위한 것으로 본 발명을 제한하기 위한 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to the following examples, but the following examples are for illustrative purposes only and are not intended to limit the present invention.
합성예 1: 2,7-디페닐-9,10-(o-톨릴)안트라센의 합성Synthesis Example 1 Synthesis of 2,7-diphenyl-9,10- (o-tolyl) anthracene
1-1: 2,7-디페닐-안트라퀴논의 합성1-1: Synthesis of 2,7-diphenyl-anthraquinone
2L 둥근바닥 플라스크에 2,7-디브로모안트라퀴논(2,7-dibromoanthraquinone) 71.0 g (0.194 mol), 페닐보론산 (phenyl boronic acid) 71.0 g (0.582 mol), 탄산칼륨 80.4 g (0.582 mol), Pd(PPh3)4 11.24 g (0.010 mol), 물 300 ml, 톨루엔 1100 ml 및 1,4-dioxane 110 ml를 넣고, 24 시간 동안 환류 냉각하며 반응시켰다. 반응 종료 후, 반응 결과물을 상온으로 냉각한 후, 다이클로로메탄으로 세척하면서 여과하였다. 이어서, 여액을 층분리하여 유기층을 물로 3회 세척한 후, 감압 농축 후, 메탄올로 결정을 석출시킨 다음, 다시 메탄올로 세척하면서 여과하였다. 여과물을 감압 건조하여, 2,7-디페닐안트라퀴논 (2,7-diphenylanthraquinone) 57.3 g을 제조하였다.In a 2 L round bottom flask, 71.0 g (0.194 mol) of 2,7-dibromoanthraquinone, 71.0 g (0.582 mol) of phenyl boronic acid, and 80.4 g (0.582 mol) of potassium carbonate ), Pd (PPh 3 ) 4 11.24 g (0.010 mol), 300 ml of water, 1100 ml of toluene and 110 ml of 1,4-dioxane were added and reacted under reflux for 24 hours. After the reaction was completed, the reaction product was cooled to room temperature, and then filtered while washing with dichloromethane. Subsequently, the filtrate was separated and the organic layer was washed three times with water, concentrated under reduced pressure, precipitated with crystals of methanol, and then filtered with washing with methanol. The filtrate was dried under reduced pressure to prepare 57.3 g of 2,7-diphenylanthraquinone.
1-2: 2,7-디페닐-9,10-디하이드록시-9,10-디(o-톨릴)안트라센의 합성1-2: Synthesis of 2,7-diphenyl-9,10-dihydroxy-9,10-di (o-tolyl) anthracene
1 L의 둥근바닥 플라스크에 2-브로모톨루엔 (2-bromotoluene) 67.4 ml (0.556 mol), THF 500 mL를 넣은 후, 영하 78 까지 냉각시켰다. 이어서, 노르말부틸리튬 67.4 mL (0.417 mol)를 천천히 적가하고, 동일한 온도에서 1시간 동안 교반한 후, 2,7-디페닐안트라퀴논 (2,7-diphenylanthraquinone) 50 g (0.139 mol)를 첨가하였다. 상기 반응 결과물을 상온으로 승온한 후, 12시간 동안 교반하였고, 반응물에 2N 염산 200 ml를 첨가하였다. 결과물을 층 분리하여 유기층을 MgSO4로 건조하고, 여과 및 여액을 농축하여 2,7-디페닐-9,10-디하이드록시-9,10-디(o-톨릴)안트 라센을 얻었다.In a 1 L round bottom flask, 67.4 ml (0.556 mol) of 2-bromotoluene was added to 500 mL of THF, and then cooled to minus 78. Then 67.4 mL (0.417 mol) of normalbutyllithium was slowly added dropwise, stirred at the same temperature for 1 hour, and then 50 g (0.139 mol) of 2,7-diphenylanthraquinone was added. . The reaction product was warmed to room temperature, stirred for 12 hours, and 200 ml of 2N hydrochloric acid was added to the reaction. The resulting layer was separated and the organic layer was dried over MgSO 4 , filtered and the filtrate was concentrated to give 2,7-diphenyl-9,10-dihydroxy-9,10-di (o-tolyl) anthracene.
1-3: 2,7-디페닐-9,10-(o-톨릴)안트라센의 합성1-3: Synthesis of 2,7-diphenyl-9,10- (o-tolyl) anthracene
2 L의 둥근바닥 플라스크에 2,7-디페닐-9,10-디하이드록시-9,10-디(o-톨릴)안트라센을 넣은 후, KI 64.6 g (0.389 mol), NaH2PO2-H2O 69.7 g (0.79 mol), 아세트산 1500 ml를 첨가하여 5시간 동안 환류 냉각시켰다. 결과물은 상온으로 냉각하고, 여과한 다음, 과량의 물과 메탄올로 세척하였다. 세척 결과물을 건조시킨 다음, 톨루엔으로 재결정시켜서 생성된 고체를 여과한 후, 감압 건조하여 2,7-디페닐-9,10-(o-톨릴)안트라센(2,7-diphenyl-9,10-di(o-tolyl)anthracene) 29 g (2,7-디페닐안트라퀴논 대비 수득률 41%)을 제조하였다.2,7-diphenyl-9,10-dihydroxy-9,10-di (o-tolyl) anthracene was added to a 2 L round bottom flask, followed by KI 64.6 g (0.389 mol), NaH 2 PO 2- 69.7 g (0.79 mol) of H 2 O, 1500 ml of acetic acid were added and refluxed for 5 hours. The result was cooled to room temperature, filtered and washed with excess water and methanol. The washed result was dried and then recrystallized with toluene, and the resulting solid was filtered and dried under reduced pressure to give 2,7-diphenyl-9,10- (o-tolyl) anthracene (2,7-diphenyl-9,10- 29 g of di (o-tolyl) anthracene) (41% yield compared to 2,7-diphenylanthraquinone) were prepared.
[ 1H NMR(CDCl3) : d 7.0~8.0 (Ar-H, m ,24H), d 2.35 ~ 2.40 (CH3, s, 6H), DSC : 273, HPLC : 99.5% ] [ 1 H NMR (CDCl 3 ): d 7.0 ~ 8.0 (Ar-H, m, 24H), d 2.35 ~ 2.40 (CH 3 , s, 6H), DSC: 273, HPLC: 99.5%]
합성예 2 :2,7-디페닐-9,10-(m-톨릴)안트라센의 합성Synthesis Example 2 Synthesis of 2,7-diphenyl-9,10- (m-tolyl) anthracene
2-1: 2,7-디페닐-9,10-디하이드록시-9,10-디(m-톨릴)안트라센의 합성2-1: Synthesis of 2,7-diphenyl-9,10-dihydroxy-9,10-di (m-tolyl) anthracene
500 ml의 둥근바닥 플라스크에 3-브로모톨루엔 (3-bromotoluene) 20.4 ml (0.17 mol), THF 50 mL를 넣은 후, 영하 78 까지 냉각시켰다. 이어서, 노르말부틸리튬 78.6 mL (0.126 mol)를 천천히 적가하고, 동일한 온도에서 1시간 동안 교반한 후, 2,7-디페닐안트라퀴논 (2,6-diphenylanthraquinone) 15.2 g (0.042 mol)를 첨 가하였다. 상기 반응 결과물을 상온으로 승온한 후, 12시간 동안 교반하였고, 반응물에 2N 염산 30 ml를 첨가하였다. 결과물을 층 분리하여 유기층을 MgSO4로 건조하고, 여과 및 여액을 농축하여 2,7-디페닐-9,10-디하이드록시-9,10-디(m-톨릴)안트라센을 얻었다. In a 500 ml round bottom flask, 20.4 ml (0.17 mol) of 3-bromotoluene and 50 mL of THF were added and cooled to minus 78. Then 78.6 mL (0.126 mol) of normalbutyllithium was slowly added dropwise, stirred for 1 hour at the same temperature, and then 15.2 g (0.042 mol) of 2,7-diphenylanthraquinone was added. It was. The reaction product was warmed to room temperature, stirred for 12 hours, and 30 ml of 2N hydrochloric acid was added to the reaction. The resulting layer was separated and the organic layer was dried over MgSO 4 , filtered and the filtrate was concentrated to give 2,7-diphenyl-9,10-dihydroxy-9,10-di (m-tolyl) anthracene.
2-2: 2,7-디페닐-9,10-(m-톨릴)안트라센의 합성2-2: Synthesis of 2,7-diphenyl-9,10- (m-tolyl) anthracene
2 L의 둥근바닥 플라스크에 2,7-디페닐-9,10-디하이드록시-9,10-디(m-톨릴)안트라센을 넣은 후, KI 19.5 g (0.12 mol), NaH2PO2-H2O 21.0 g (0.24 mol), 아세트산 250 ml를 첨가하여 5시간 동안 환류 냉각시켰다. 결과물은 상온으로 냉각하고, 여과한 다음, 과량의 물과 메탄올로 세척하였다. 세척 결과물을 건조시킨 다음, 톨루엔으로 재결정시켜서 생성된 고체를 여과한 후, 감압 건조하여 2,7-디페닐-9,10-(m-톨릴)안트라센(2,7-diphenyl-9,10-di(m-tolyl)anthracene) 10.7 g (2,7-디페닐안트라퀴논 대비 수득률 50%)을 제조하였다.2,7-diphenyl-9,10-dihydroxy-9,10-di (m-tolyl) anthracene was added to a 2 L round bottom flask, followed by KI 19.5 g (0.12 mol), NaH 2 PO 2 − 21.0 g of H 2 O (0.24 mol) and 250 ml of acetic acid were added to reflux for 5 hours. The result was cooled to room temperature, filtered and washed with excess water and methanol. The washed result was dried and then recrystallized with toluene, and the resulting solid was filtered and dried under reduced pressure to give 2,7-diphenyl-9,10- (m-tolyl) anthracene (2,7-diphenyl-9,10- 10.7 g of di (m-tolyl) anthracene) (50% yield compared to 2,7-diphenylanthraquinone) was prepared.
[ 1H NMR(CDCl3) : d 7.3~8.0 (Ar-H, m ,24H), d 2.54 ~ 2.51 (CH3, d, 6, DSC : 262, HPLC : 99.2% ][ 1 H NMR (CDCl 3 ): d 7.3 ~ 8.0 (Ar-H, m, 24H), d 2.54 ~ 2.51 (CH 3 , d, 6, DSC: 262, HPLC: 99.2%)
합성예 3: 2,6-디페닐-9,10-(m -톨릴)안트라센의 합성Synthesis Example 3: Synthesis of 2,6-diphenyl-9,10- (m-tolyl) anthracene
3-1: 2,6-디페닐안트라퀴논의 합성3-1: Synthesis of 2,6-diphenylanthraquinone
2L 둥근바닥 플라스크에 2,7-디브로모안트라퀴논 (2,7- dibromoanthraquinone) 53.3 g (0.15 mol), 페닐보론산 (phenyl boronic acid) 53.5 g (0.44 mol), 탄산칼륨 60.3 g (0.44 mol), Pd(PPh3)4 8.43 g (0.007 mol), 물 250 ml, 톨루엔 800 ml 및 1,4-dioxane 80 ml를 넣고, 12 시간 동안 환류 냉각하며 반응시켰다. 반응 종료 후, 반응 결과물을 상온으로 냉각한 후, 다이클로로메탄으로 세척하면서 여과하였다. 이어서, 여액을 층분리하여 유기층을 물로 3회 세척한 후, 감압 농축한 후, 메탄올로 결정을 석출시킨 다음, 다시 메탄올로 세척하면서 여과하였다. 여과물을 감압 건조하여, 2,7-디페닐안트라퀴논 (2,7-diphenylanthraquinone) 44.2 g을 제조하였다.53.3 g (0.15 mol) of 2,7-dibromoanthraquinone, 53.5 g (0.44 mol) of phenyl boronic acid, 60.3 g (0.44 mol) of potassium carbonate in a 2 L round bottom flask ), Pd (PPh 3 ) 4 8.43 g (0.007 mol), 250 ml of water, 800 ml of toluene and 80 ml of 1,4-dioxane were added and reacted under reflux for 12 hours. After the reaction was completed, the reaction product was cooled to room temperature, and then filtered while washing with dichloromethane. Subsequently, the filtrate was separated and the organic layer was washed three times with water, concentrated under reduced pressure, and then precipitated with crystals of methanol, followed by filtration with washing with methanol. The filtrate was dried under reduced pressure to give 44.2 g of 2,7-diphenylanthraquinone.
3-2: 2,6-디페닐-9,10-디하이드록시-9,10-디(m-톨릴)안트라센의 합성3-2: Synthesis of 2,6-diphenyl-9,10-dihydroxy-9,10-di (m-tolyl) anthracene
500 ml의 둥근바닥 플라스크에 3-브로모톨루엔 (3-bromotoluene) 15.3 ml (0.13 mol), THF 40 mL를 넣은 후, 영하 78 까지 냉각시켰다. 이어서, 노르말-부틸리튬 58.9 mL (0.095 mol)를 천천히 적가하고, 동일한 온도에서 1시간 동안 교반 후, 2,6-디페닐안트라퀴논 (2,6-diphenylanthraquinone) 11.4 g (0.032 mol)를 첨가하였다. 상기 반응 결과물을 상온으로 승온한 후, 12시간 동안 교반하였고, 반응물에 2N 염산 50 ml를 첨가하였다. 결과물을 층 분리하여 유기층을 MgSO4로 건조하고, 여과 및 여액을 농축하여 2,6-디페닐-9,10-디하이드록시-9,10-디(m-톨릴)안트라센을 얻었다.In a 500 ml round bottom flask, 15.3 ml (0.13 mol) of 3-bromotoluene was added and 40 mL of THF, and then cooled to minus 78. Then, 58.9 mL (0.095 mol) of normal-butyllithium was slowly added dropwise, stirred for 1 hour at the same temperature, and then 11.4 g (0.032 mol) of 2,6-diphenylanthraquinone was added. . The reaction product was warmed to room temperature, stirred for 12 hours, and 50 ml of 2N hydrochloric acid was added to the reaction. The resulting layer was separated and the organic layer was dried over MgSO 4 , filtered and the filtrate was concentrated to give 2,6-diphenyl-9,10-dihydroxy-9,10-di (m-tolyl) anthracene.
3-3: 2,6-디페닐-9,10-(m-톨릴)안트라센의 합성3-3: Synthesis of 2,6-diphenyl-9,10- (m-tolyl) anthracene
1 L의 둥근바닥 플라스크에 2,6-디페닐-9,10-디하이드록시-9,10-디(m-톨릴)안트라센을 넣은 후, KI 14.6 g (0.09 mol), NaH2PO2-H2O 15.8 g (0.18 mol), 아세트산 200 ml를 첨가하여 5시간 동안 환류 냉각시켰다. 결과물은 상온으로 냉각하고, 여과한 다음, 과량의 물과 메탄올로 세척하였다. 세척 결과물을 건조시킨 다음, 톨루엔으로 재결정시켜서 생성된 고체를 여과한 후, 감압 건조하여 2,6-디페닐-9,10-(m-톨릴)안트라센 [2,6-diphenyl-9,10-di(m -tolyl)anthracene] 6.42 g (2,6-디페닐안트라퀴논 대비 수득률 40%)을 제조하였다.2,6-diphenyl-9,10-dihydroxy-9,10-di (m-tolyl) anthracene was added to a 1 L round bottom flask, followed by KI 14.6 g (0.09 mol), NaH 2 PO 2- 15.8 g (0.18 mol) of H 2 O, 200 ml of acetic acid were added, and the mixture was cooled to reflux for 5 hours. The result was cooled to room temperature, filtered and washed with excess water and methanol. The washed result was dried and then recrystallized with toluene, and the resulting solid was filtered and dried under reduced pressure to give 2,6-diphenyl-9,10- (m-tolyl) anthracene [2,6-diphenyl-9,10- 6.42 g of di (m-tolyl) anthracene] (a yield of 40% relative to 2,6-diphenylanthraquinone) was prepared.
[ 1H NMR(CDCl3) : d 7.4 ~ 8.2 (Ar-H, m ,24H), d 2.2 ~ 2.6 (CH3, s, 6H), DSC : 331, HPLC : 99.5% ][ 1 H NMR (CDCl 3 ): d 7.4-8.2 (Ar-H, m, 24H), d 2.2-2.6 (CH 3 , s, 6H), DSC: 331, HPLC: 99.5%]
합성예 4: 2,7-디페닐-9,10-(p-메톡시페닐)안트라센의 합성Synthesis Example 4 Synthesis of 2,7-diphenyl-9,10- (p-methoxyphenyl) anthracene
4-1: 2,7-디페닐-9,10-디하이드록시-9,10-디(p-메톡시페닐)안트라센의 합성 4-1: Synthesis of 2,7-diphenyl-9,10-dihydroxy-9,10-di (p-methoxyphenyl) anthracene
500 ml의 둥근바닥 플라스크에 4-브로모애니솔 (4-bromoanisole) 25.4 g (0.14 mol), THF 50 mL를 넣은 후, 영하 78 까지 냉각시켰다. 이어서, 노르말부틸리튬 62.9 mL (0.1 mol)를 천천히 적가하고, 동일한 온도에서 1시간 동안 교반한 후, 2,7-디페닐안트라퀴논 (2,6-diphenylanthraquinone) 12.2 g (0.034 mol)를 첨가하였다. 상기 반응 결과물을 상온으로 승온한 후, 12시간 동안 교반하였고, 반응물에 2N 염산 50 ml를 첨가하였다. 결과물을 층 분리하여 유기층을 MgSO4로 건조하 고, 여과 및 여액을 농축하여 2,7-디페닐-9,10-디하이드록시-9,10-디(p-메톡시페닐)안트라센을 얻었다. Into a 500 ml round bottom flask, 25.4 g (0.14 mol) of 4-bromoanisole and 50 mL of THF were added and cooled to minus 78. Then 62.9 mL (0.1 mol) of normalbutyllithium was slowly added dropwise, stirred at the same temperature for 1 hour, and then 12.2 g (0.034 mol) of 2,7-diphenylanthraquinone was added. . The reaction product was warmed to room temperature, stirred for 12 hours, and 50 ml of 2N hydrochloric acid was added to the reaction. The resulting layer was separated and the organic layer was dried over MgSO 4 , filtered and the filtrate was concentrated to give 2,7-diphenyl-9,10-dihydroxy-9,10-di (p-methoxyphenyl) anthracene. .
4-2: 2,7-디페닐-9,10-(p-메톡시페닐)안트라센의 합성4-2: Synthesis of 2,7-diphenyl-9,10- (p-methoxyphenyl) anthracene
1 L의 둥근바닥 플라스크에 반응식 2로부터 얻은 2,7-디페닐-9,10-디하이드록시-9,10-디(p-메톡시페닐)안트라센을 넣은 후, KI 15.6 g (0.1 mol), NaH2PO2-H2O 16.8 g (0.19 mol), 아세트산 200 ml를 첨가하여 5시간 동안 환류 냉각시켰다. 결과물은 상온으로 냉각하고, 여과한 다음, 과량의 물과 메탄올로 세척하였다. 세척 결과물을 건조시킨 다음, 톨루엔으로 재결정시켜서 생성된 고체를 여과한 후, 감압 건조하여 2,7-디페닐-9,10-(p-매톡시페닐)안트라센 [2,7-diphenyl-9,10-di(p-methoxy- phenyl)anthracene] 8.9 g (2,7-디페닐안트라퀴논 대비 수득률 55%)을 제조하였다. Into a 1 L round bottom flask was placed 2,7-diphenyl-9,10-dihydroxy-9,10-di (p-methoxyphenyl) anthracene obtained from Scheme 2, followed by KI 15.6 g (0.1 mol). 16.8 g (0.19 mol) of NaH 2 PO 2 -H 2 O and 200 ml of acetic acid were added thereto, and the mixture was cooled to reflux for 5 hours. The result was cooled to room temperature, filtered and washed with excess water and methanol. The washed result was dried and then recrystallized with toluene, and the resulting solid was filtered and dried under reduced pressure to give 2,7-diphenyl-9,10- (p-methoxyphenyl) anthracene [2,7-diphenyl-9, 10-di (p-methoxy-phenyl) anthracene] 8.9 g (55% yield compared to 2,7-diphenylanthraquinone) was prepared.
[ 1H NMR(CDCl3) : d 6.9 ~ 8.1 (Ar-H, m ,24H), d 3.8 ~ 4.1 (OCH3, s, 6H), DSC : 330, HPLC : 99.2% ][ 1 H NMR (CDCl 3 ): d 6.9-8.1 (Ar-H, m, 24H), d 3.8-4.1 (OCH 3 , s, 6H), DSC: 330, HPLC: 99.2%]
합성예 5: 2,7-디페닐-9,10-(p-트리메틸실릴페닐)안트라센의 합성Synthesis Example 5 Synthesis of 2,7-diphenyl-9,10- (p-trimethylsilylphenyl) anthracene
5-1: 2,7-디페닐-9,10-디하이드록시-9,10-디(p-트리메틸실릴페닐)안트라센의 합성5-1: Synthesis of 2,7-diphenyl-9,10-dihydroxy-9,10-di (p-trimethylsilylphenyl) anthracene
1 L의 둥근바닥 플라스크에 4-트리메틸실릴브로모벤젠 (4-trimethylsilyl bromobenzene) 50 g (0.21 mol), THF 100 mL를 넣은 후, 영하 78 까지 냉각시켰다. 이어서, 노르말부틸리튬 97.5 mL (0.16 mol)를 천천히 적가하고, 동일한 온도에서 1시간 동안 교반한 후, 2,7-디페닐안트라퀴논 (2,6-diphenylanthraquinone) 18.9 g (0.053 mol)를 첨가하였다. 상기 반응 결과물을 상온으로 승온한 후, 12시간 동안 교반하였고, 반응물에 2N 염산 80 ml를 첨가하였다. 결과물을 층 분리하여 유기층을 MgSO4로 건조하고, 여과 및 여액을 농축하여 2,7-디페닐-9,10-디하이드록시-9,10-디(p-트리메틸실릴페닐)안트라센을 얻었다.50 g (0.21 mol) of 4-trimethylsilyl bromobenzene and 100 mL of THF were added to a 1 L round bottom flask, and the mixture was cooled to minus 78 degrees. Then 97.5 mL (0.16 mol) of normal butyllithium was slowly added dropwise, stirred for 1 hour at the same temperature, and then 18.9 g (0.053 mol) of 2,7-diphenylanthraquinone was added. . The reaction product was warmed to room temperature, stirred for 12 hours, and 80 ml of 2N hydrochloric acid was added to the reaction. The resulting layer was separated and the organic layer was dried over MgSO 4 , filtered and the filtrate was concentrated to give 2,7-diphenyl-9,10-dihydroxy-9,10-di (p-trimethylsilylphenyl) anthracene.
5-2: 2,7-디페닐-9,10-(p-트리메틸실릴페닐)안트라센의 합성5-2: Synthesis of 2,7-diphenyl-9,10- (p-trimethylsilylphenyl) anthracene
1 L의 둥근바닥 플라스크에 2,7-디페닐-9,10-디하이드록시-9,10-디(p-트리메틸실릴)안트라센을 넣은 후, KI 24.2 g (0.15 mol), NaH2PO2-H2O 26.8 g (0.29 mol), 아세트산 500 ml를 첨가하여 5시간 동안 환류냉각시켰다. 결과물은 상온으로 냉각하고, 여과한 다음, 과량의 물과 메탄올로 세척하였다. 세척 결과물을 건조시킨 다음, 톨루엔으로 재결정시켜서 생성된 고체를 여과한 후, 감압 건조하여 2,7-디페닐-9,10-(p-트리메틸실릴페닐)안트라센 [2,7-diphenyl-9,10-di(p-trimethylsilylphenyl) anthracene] 8.7 g (2,7-디페닐안트라퀴논 대비 수득률 35%)을 제조하였다. 2,7-diphenyl-9,10-dihydroxy-9,10-di (p-trimethylsilyl) anthracene was added to a 1 L round bottom flask, followed by KI 24.2 g (0.15 mol), NaH 2 PO 2 26.8 g (0.29 mol) of -H 2 O and 500 ml of acetic acid were added to reflux for 5 hours. The result was cooled to room temperature, filtered and washed with excess water and methanol. The washed result was dried and then recrystallized with toluene, and the resulting solid was filtered and dried under reduced pressure to give 2,7-diphenyl-9,10- (p-trimethylsilylphenyl) anthracene [2,7-diphenyl-9, 10-di (p-trimethylsilylphenyl) anthracene] 8.7 g (35% yield compared to 2,7-diphenylanthraquinone) was prepared.
[ 1H NMR(CDCl3) : d 7.4~8.3 (Ar-H, m ,24H), d 1.2 ~ 2.0 (TMS, s, 18H), DSC : 273, HPLC : 99.5% ][ 1 H NMR (CDCl 3 ): d 7.4-8.3 (Ar-H, m, 24H), d 1.2-2.0 (TMS, s, 18H), DSC: 273, HPLC: 99.5%]
합성예 6: 2,7-디(p-톨릴)-9,10-(m-톨릴)안트라센의 합성Synthesis Example 6 Synthesis of 2,7-di (p-tolyl) -9,10- (m-tolyl) anthracene
6-1: 2,7-디(p-톨릴)안트라퀴논의 합성6-1: Synthesis of 2,7-di (p-tolyl) anthraquinone
2L 둥근바닥 플라스크에 2,7-디브로모안트라퀴논 (2,7-dibromoanthraquinone) 71.0 g (0.194 mol), 4-메틸페닐보론산 (4-methtl phenyl boronic acid) 79.0 g (0.582 mol), 탄산칼륨 80.4 g (0.582 mol), Pd(PPh3)4 11.24 g (0.010 mol), 물 300 ml, 톨루엔 1100 ml 및 1,4-dioxane 110 ml를 넣고, 24 시간 동안 환류 냉각하며 반응시켰다. 반응 종료 후, 반응 결과물을 상온으로 냉각한 후, 다이클로로메탄으로 세척하면서 여과하였다. 이어서, 여액을 층분리하여 유기층을 물로 3회 세척한 후, 감압 농축한 후, 메탄올로 결정을 석출시킨 다음, 다시 메탄올로 세척하면서 여과하였다. 여과물을 감압 건조하여, 2,7-디(p-톨릴)안트라퀴논[2,7-di(p-tolyl)phenylanthraquinone] 43.3 g을 제조하였다.71.0 g (0.194 mol) of 2,7-dibromoanthraquinone, 79.0 g (0.582 mol) of 4-methtl phenyl boronic acid in a 2 L round bottom flask, potassium carbonate 80.4 g (0.582 mol), Pd (PPh 3 ) 4 11.24 g (0.010 mol), 300 ml of water, 1100 ml of toluene, and 110 ml of 1,4-dioxane were added and reacted with reflux for 24 hours. After the reaction was completed, the reaction product was cooled to room temperature, and then filtered while washing with dichloromethane. Subsequently, the filtrate was separated and the organic layer was washed three times with water, concentrated under reduced pressure, and then precipitated with crystals of methanol, followed by filtration with washing with methanol. The filtrate was dried under reduced pressure to prepare 43.3 g of 2,7-di (p-tolyl) anthraquinone [2,7-di (p-tolyl) phenylanthraquinone].
6-2: 2,7-디(p-톨릴)-9,10-디하이드록시-9,10-디(m-톨릴)안트라센의 합성6-2: Synthesis of 2,7-di (p-tolyl) -9,10-dihydroxy-9,10-di (m-tolyl) anthracene
1 L의 둥근바닥 플라스크에 3-브로모톨루엔 (2-bromotoluene) 67.4 ml (0.556 mol), THF 500 mL를 넣은 후, 영하 78 까지 냉각시켰다. 이어서, 노르말부 틸리튬 67.4 mL (0.417 mol)를 천천히 적가하고, 동일한 온도에서 1시간 동안 교반한 후, 2,7-디(p-톨릴)안트라퀴논 47 g (0.130 mol)를 첨가하였다. 상기 반응 결과물을 상온으로 승온한 후, 12시간 동안 교반하였고, 반응물에 2N 염산 300 ml를 첨가하였다. 결과물을 층 분리하여 유기층을 MgSO4로 건조하고, 여과 및 여액을 농축하여 2,7-디(p-톨릴)-9,10-디하이드록시-9,10-디(m-톨릴)안트라센을 얻었다.67.4 ml (0.556 mol) of 3-bromotoluene and 500 mL of THF were added to a 1 L round bottom flask, followed by cooling to -78 ° C. Then 67.4 mL (0.417 mol) of normal part lithium was slowly added dropwise, stirred for 1 hour at the same temperature, and then 47 g (0.130 mol) of 2,7-di (p-tolyl) anthraquinone was added. The reaction product was warmed to room temperature, stirred for 12 hours, and 300 ml of 2N hydrochloric acid was added to the reaction. The resulting layer was separated and the organic layer was dried over MgSO 4 , filtered and the filtrate was concentrated to give 2,7-di (p-tolyl) -9,10-dihydroxy-9,10-di (m-tolyl) anthracene. Got it.
6-3: 2,7-디(p-톨릴)-9,10-(m-톨릴)안트라센의 합성6-3: Synthesis of 2,7-di (p-tolyl) -9,10- (m-tolyl) anthracene
2 L의 둥근바닥 플라스크에 2,7-디(p-톨릴)-9,10-디하이드록시-9,10-디(m-톨릴)안트라센을 넣은 후, KI 64.6 g (0.389 mol), NaH2PO2-H2O 69.7 g (0.79 mol), 아세트산 1500 ml를 첨가하여 5시간 동안 환류 냉각시켰다. 결과물은 상온으로 냉각하고, 여과한 다음, 과량의 물과 메탄올로 세척하였다. 세척 결과물을 건조시킨 다음, 톨루엔으로 재결정시켜서 생성된 고체를 여과한 후, 감압 건조하여 2,7-디(p-톨릴)-9,10-(m-톨릴)안트라센(2,7-di(p-tolyl)-9,10-di(m-tolyl)-anthracene) 34 g (2,7-디(p-톨릴)안트라퀴논 대비 수득률 41%)을 제조하였다.2,7-di (p-tolyl) -9,10-dihydroxy-9,10-di (m-tolyl) anthracene was added to a 2 L round bottom flask, followed by KI 64.6 g (0.389 mol), NaH 69.7 g (0.79 mol) of 2 PO 2 -H 2 O, 1500 ml of acetic acid were added and refluxed for 5 hours. The result was cooled to room temperature, filtered and washed with excess water and methanol. The washed result was dried and then recrystallized with toluene, and the resulting solid was filtered and dried under reduced pressure to give 2,7-di (p-tolyl) -9,10- (m-tolyl) anthracene (2,7-di ( 34 g of p-tolyl) -9,10-di (m-tolyl) -anthracene) (41% yield compared to 2,7-di (p-tolyl) anthraquinone) were prepared.
[ 1H NMR(CDCl3) : d 7.1 ~ 8.1 (Ar-H, m ,22H), d 2.1 ~ 2.3 (CH3, s, 6H), 2.4 ~ 2.7 (CH3, s, 6H), DSC : 261, HPLC : 99.7% ][ 1 H NMR (CDCl 3 ): d 7.1 to 8.1 (Ar-H, m, 22H), d 2.1 to 2.3 (CH 3 , s, 6H), 2.4 to 2.7 (CH 3 , s, 6H), DSC: 261, HPLC: 99.7%]
합성예 7: 2,6-디(m-톨릴)-9,10-디페닐안트라센의 합성Synthesis Example 7 Synthesis of 2,6-di (m-tolyl) -9,10-diphenylanthracene
7-1: 2,6-디브로모-9,10-디하이드록시-9,10-디페닐안트라센의 합성7-1: Synthesis of 2,6-dibromo-9,10-dihydroxy-9,10-diphenylanthracene
5L 둥근바닥 플라스크에 브로모벤젠 (bromobenzene) 129.5 ml (1.23 mol), THF 2250 mL를 넣은 후, 영하 78 까지 냉각시켰다. 이어서, 노르말부틸리튬 666.3 mL (1.07 mol)를 천천히 적가하고, 동일한 온도에서 1시간 동안 교반한 후, 2,6-디브로모안트라퀴논 150.1 g (0.41 mol)를 첨가하였다. 상기 반응 결과물을 상온으로 승온한 후, 12시간 동안 교반하였고, 반응물에 2N 염산 1600 ml를 첨가하였다. 결과물을 층 분리하여 유기층을 MgSO4로 건조하고, 여과 및 여액을 농축하여 2,6-디브로모-9,10-디하이드록시-9,10-디페닐안트라센을 하였다. 129.5 ml (1.23 mol) of bromobenzene and 2250 mL of THF were added to a 5 L round bottom flask, and the mixture was cooled to minus 78 degrees. Then 666.3 mL (1.07 mol) of normalbutyllithium was slowly added dropwise, stirred for 1 hour at the same temperature, and then 150.1 g (0.41 mol) of 2,6-dibromoanthraquinone was added. The reaction product was warmed to room temperature, stirred for 12 hours, and 1600 ml of 2N hydrochloric acid was added to the reaction. The resulting layer was separated and the organic layer was dried over MgSO 4 , filtered and the filtrate was concentrated to give 2,6-dibromo-9,10-dihydroxy-9,10-diphenylanthracene.
7-2: 2,6-디브로모-9,10-디페닐안트라센의 합성7-2: Synthesis of 2,6-dibromo-9,10-diphenylanthracene
3 L의 둥근바닥 플라스크에 2,6-디브로모-9,10-디하이드록시-9,10-디페닐안트라센을 넣은 후, KI 204.2 g (1.23 mol), NaH2PO2-H2O 216.4 g (2.46 mol), 아세트산 1500 ml를 첨가하여 5시간 동안 환류 냉각시켰다. 결과물은 상온으로 냉각하고, 여과한 다음, 과량의 물과 메탄올로 세척하였다. 세척 결과물을 건조시킨 다음, 톨루엔으로 재결정시켜서 생성된 고체를 여과한 후, 감압 건조하여 2,6-디브로모-9,10-디페닐안트라센 (2,6-dibromo-9,10-diphenylanthracene) 109.0 g (2,6-디브로모안트라퀴논 대비 수득률 54.5 %)을 제조하였다.2,6-dibromo-9,10-dihydroxy-9,10-diphenylanthracene was added to a 3 L round bottom flask, followed by KI 204.2 g (1.23 mol), NaH 2 PO 2 -H 2 O 216.4 g (2.46 mol), 1500 ml of acetic acid were added and reflux cooled for 5 hours. The result was cooled to room temperature, filtered and washed with excess water and methanol. The washed result was dried and then recrystallized with toluene, and the resulting solid was filtered and dried under reduced pressure to give 2,6-dibromo-9,10-diphenylanthracene (2,6-dibromo-9,10-diphenylanthracene). 109.0 g (54.5% yield over 2,6-dibromoanthraquinone) were prepared.
7-3: 2,6-디(m-톨릴)-9,10-디페닐안트라센의 합성7-3: Synthesis of 2,6-di (m-tolyl) -9,10-diphenylanthracene
250 ml 둥근바닥 플라스크에 2,6-디브로모-9,10-디페닐안트라센 5.0 g (10.2 mmol), m-톨릴보론산 (m-tolylboronic acid) 4.2 g (30.6 mmol), 탄산칼륨 8.5 g (61.4 mmol), Pd(PPh3)4 0.24 g (0.2 mmol), 물 15.4 ml, 톨루엔 30.8 ml 및 1,4-dioxane 15.4 ml를 넣고, 24 시간 동안 환류 냉각하며 반응시켰다. 반응 종료 후, 반응 결과물을 상온으로 냉각한 후, 생성된 고체를 여과하였다. 고체를 뜨거운 톨루엔에 녹인 후, 여과하였다. 상온으로 냉각하여 결정을 석출시킨 다음, 여과하였다. 2회 반복한 다음, 여과물을 감압건조하여, 2,6-디(m-톨릴)-9,10-디페닐안트라센(2,6-di(m-tolyl)-9,10-diphenylanthracene) 2.6 g (수득율 49.7 %)을 합성하였다.In a 250 ml round bottom flask, 5.0 g (10.2 mmol) of 2,6-dibromo-9,10-diphenylanthracene, 4.2 g (30.6 mmol) of m-tolylboronic acid, 8.5 g of potassium carbonate (61.4 mmol), 0.24 g (0.2 mmol) of Pd (PPh 3 ) 4 , 15.4 ml of water, 30.8 ml of toluene, and 15.4 ml of 1,4-dioxane were added thereto, and reacted with reflux for 24 hours. After the reaction was completed, the reaction product was cooled to room temperature, and then the produced solid was filtered. The solid was dissolved in hot toluene and then filtered. After cooling to room temperature, crystals were precipitated and filtered. After repeating twice, the filtrate was dried under reduced pressure to give 2,6-di (m-tolyl) -9,10-diphenylanthracene ( 2,6-di (m-tolyl) -9,10-diphenylanthracene) 2.6 g (yield 49.7%) was synthesized.
[ 1H NMR(CDCl3) : d 7.78 ~ 7.65 (Ar-H, m, 12H), d 7.59 ~ 7.56 (Ar-H, m, 4H), d 7.36 ~ 7.32 (Ar-H, m, 6H), d 7.19 ~ 7.17 (Ar-H, m, 2H), 2.34 (CH3, s, 6H), DSC : 290.3 , HPLC : 99.6 % ][ 1 H NMR (CDCl 3 ): d 7.78-7.65 (Ar-H, m, 12H), d 7.59-7.56 (Ar-H, m, 4H), d 7.36-7.32 (Ar-H, m, 6H) , d 7.19-7.17 (Ar-H, m, 2H), 2.34 (CH 3 , s, 6H), DSC: 290.3, HPLC: 99.6%]
합성예 8: 2,6-디(페닐-d5)-9,10-디페닐안트라센의 합성Synthesis Example 8 Synthesis of 2,6-di (phenyl-d5) -9,10-diphenylanthracene
8-1: 2,6-디(페닐-d5)-9,10-디페닐안트라센의 합성8-1: Synthesis of 2,6-di (phenyl-d5) -9,10-diphenylanthracene
250 ml 둥근바닥 플라스크에 2,6-디브로모-9,10-디페닐안트라센 8.0 g (16.4 mmol), 페닐-d5-보론산 (phenyl-d5-boronic acid) 6.2 g (49 mmol), 탄산칼륨 13.6 g (98 mmol), Pd(PPh3)4 0.8 g (0.66 mmol), 물 40 ml, 톨루엔 80 ml 및 1,4-dioxane 40 ml를 넣고, 24 시간 동안 환류 냉각하며 반응시켰다. 반응 종료 후, 반응 결과물을 상온으로 냉각한 후, 생성된 고체를 여과하였다. 고체를 뜨거운 톨루엔에 녹인 후, 여과하였다. 상온으로 냉각하여 결정을 석출시킨 다음, 여과하였다. 2회 반복한 다음, 여과물을 감압 건조하여, 2,6-디(페닐-d5)-9,10-디페닐안트라센(2,6-di(phenyl- d5)-9,10-diphenylanthracene) 6.7 g (수득율 82.7 %)을 합성하였다.In a 250 ml round bottom flask, 8.0 g (16.4 mmol) of 2,6-dibromo-9,10-diphenylanthracene, 6.2 g (49 mmol) of phenyl-d5-boronic acid, carbonic acid Potassium 13.6 g (98 mmol), Pd (PPh 3 ) 4 0.8 g (0.66 mmol), 40 ml of water, 80 ml of toluene and 40 ml of 1,4-dioxane were added and reacted under reflux for 24 hours. After the reaction was completed, the reaction product was cooled to room temperature, and then the produced solid was filtered. The solid was dissolved in hot toluene and then filtered. After cooling to room temperature, crystals were precipitated and filtered. After repeating twice, the filtrate was dried under reduced pressure to give 2,6-di (phenyl-d5) -9,10-diphenylanthracene ( 2,6-di (phenyl-d5) -9,10-diphenylanthracene) 6.7 g (yield 82.7%) was synthesized.
[ 1H NMR(CDCl3) : d 7.79 ~ 7.82 (Ar-H, m, 4H), d 7.65 ~ 7.74 (Ar-H, m , 8H), d 7.57 ~ 7.59 (Ar-H, m , 4H), DSC : 334.4 , HPLC : 99.9 % ][ 1 H NMR (CDCl 3 ): d 7.79 ~ 7.82 (Ar-H, m, 4H), d 7.65 ~ 7.74 (Ar-H, m, 8H), d 7.57 ~ 7.59 (Ar-H, m, 4H) , DSC: 334.4, HPLC: 99.9%]
합성예 9: 2,6-디(2-나프틸)-9,10-디페닐안트라센의 합성Synthesis Example 9 Synthesis of 2,6-di (2-naphthyl) -9,10-diphenylanthracene
9-1: 2,6-디(2-나프틸)-9,10-디페닐안트라센의 합성9-1: Synthesis of 2,6-di (2-naphthyl) -9,10-diphenylanthracene
250 ml 둥근바닥 플라스크에 2,6-디브로모-9,10-디페닐안트라센 4. g (8.2 mmol), 2-나프틸보론산 (naphthylboronic acid) 4.2 g (24.6 mmol), 탄산칼륨 13.6 g (49.2 mmol), Pd(PPh3)4 0.19 g (0.16. mmol), 물 24.6 ml, 톨루엔 12.3 ml 및 1,4-dioxane 12.3 ml를 넣고, 24 시간 동안 환류 냉각하며 반응시켰다. 반응 종료 후, 반응 결과물을 상온으로 냉각한 후, 생성된 고체를 여과하였다. 고체를 뜨거운 톨루엔에 녹인 후, 여과하였다. 상온으로 냉각하여 결정을 석출시킨 다음, 여과하 였다. 2회 반복한 다음, 여과물을 감압 건조하여, 2,6-디(2-나프틸)-9,10-디페닐안트라센(2,6-di(2-naphthyl)-9,10-diphenylanthracene) 3.0 g (수득율 62.8 %)을 합성하였다.4 g (8.2 mmol) of 2,6-dibromo-9,10-diphenylanthracene, 4.2 g (24.6 mmol) of 2-naphthylboronic acid, 13.6 g of potassium carbonate in a 250 ml round bottom flask (49.2 mmol), 0.19 g (0.16. Mmol) of Pd (PPh 3 ) 4 , 24.6 ml of water, 12.3 ml of toluene, and 12.3 ml of 1,4-dioxane were added thereto, and reacted with reflux for 24 hours. After the reaction was completed, the reaction product was cooled to room temperature, and then the produced solid was filtered. The solid was dissolved in hot toluene and then filtered. After cooling to room temperature to precipitate a crystal, it was filtered. After repeating twice, the filtrate was dried under reduced pressure to give 2,6-di (2-naphthyl) -9,10-diphenylanthracene ( 2,6-di (2-naphthyl) -9,10-diphenylanthracene) 3.0 g (62.8% yield) were synthesized.
[ 1H NMR(CDCl3) : d 8.15 (Ar-H, s, 2H), d 7.92 ~ 8.03 (Ar-H, m, 10H), 7.62 ~ 7.79 (Ar-H, m, 14H), 7.51 ~ 7.56 (Ar-H, m, 4H), DSC : 334.9 , HPLC : 99.9 %][ 1 H NMR (CDCl 3 ): d 8.15 (Ar-H, s, 2H), d 7.92-8.03 (Ar-H, m, 10H), 7.62-7.79 (Ar-H, m, 14H), 7.51- 7.56 (Ar-H, m, 4H), DSC: 334.9, HPLC: 99.9%]
실시예 : 본 발명에 따른 유기전계발광소자의 제조Example: Fabrication of Organic Electroluminescent Device According to the Present Invention
실시예 1Example 1
ITO 글라스의 발광 면적이 2mm x 2mm가 되도록 기판 상에 패터닝한 다음 세정하였다. 상기 기판을 진공 챔버에 장착한 후, 베이스 압력이 1 x 10-6 torr가 되도록 한 다음, 공지의 방법을 사용하여, 상기 ITO 글라스 상에 CuPC (200Å, NPD (400Å), 상기 합성예 1에서 제조된 화합물 + C545T (5%) (200Å), Alq3 (350Å), LiF (5Å), Al (1000Å)의 순서로 성막하였다.The light emitting area of the ITO glass was patterned on the substrate so as to be 2 mm x 2 mm, and then washed. After mounting the substrate in a vacuum chamber, the base pressure was 1 x 10 -6 torr, and then CuPC (200 kPa, NPD (400 kPa), Synthesis Example 1 was prepared on the ITO glass using a known method. The films were formed in the order of Prepared Compound + C545T (5%) (200 Pa), Alq 3 (350 Pa), LiF (5 Pa), Al (1000 Pa).
실시예 2Example 2
합성예 1에서 제조된 화합물 대신에 상기 합성예 2에서 제조된 화합물을 사용하였다는 점을 제외하고는, 상기 실시예 1과 동일한 방법에 따라서 유기전계발광 소자를 제조하였다. An organic light emitting display device was manufactured according to the same method as Example 1 except for using the compound prepared in Synthesis Example 2 instead of the compound prepared in Synthesis Example 1.
실시예 3Example 3
합성예 1에서 제조된 화합물 대신에 상기 합성예 3에서 제조된 화합물을 사용하였다는 점을 제외하고는, 상기 실시예 1과 동일한 방법에 따라서 유기전계발광소자를 제조하였다. An organic light emitting display device was manufactured according to the same method as Example 1 except for using the compound prepared in Synthesis Example 3 instead of the compound prepared in Synthesis Example 1.
실시예 4Example 4
합성예 1에서 제조된 화합물 대신에 상기 합성예 6에서 제조된 화합물을 사용하였다는 점을 제외하고는, 상기 실시예 1과 동일한 방법에 따라서 유기전계발광소자를 제조하였다. An organic light emitting diode device was manufactured according to the same method as Example 1 except for using the compound prepared in Synthesis Example 6 instead of the compound prepared in Synthesis Example 1.
실시예 5Example 5
합성예 1에서 제조된 화합물 대신에 상기 합성예 7에서 제조된 화합물을 사용하였다는 점을 제외하고는, 상기 실시예 1과 동일한 방법에 따라서 유기전계발광소자를 제조하였다. An organic light emitting display device was manufactured according to the same method as Example 1 except for using the compound prepared in Synthesis Example 7 instead of the compound prepared in Synthesis Example 1.
실시예 6Example 6
합성예 1에서 제조된 화합물 대신에 상기 합성예 8에서 제조된 화합물을 사용하였다는 점을 제외하고는, 상기 실시예 1과 동일한 방법에 따라서 유기전계발광 소자를 제조하였다. An organic light emitting display device was manufactured according to the same method as Example 1 except for using the compound prepared in Synthesis Example 8 instead of the compound prepared in Synthesis Example 1.
실시예 7Example 7
합성예 1에서 제조된 화합물 대신에 상기 합성예 9에서 제조된 화합물을 사용하였다는 점을 제외하고는, 상기 실시예 1과 동일한 방법에 따라서 유기전계발광소자를 제조하였다. An organic light emitting diode device was manufactured according to the same method as Example 1 except for using the compound prepared in Synthesis Example 9 instead of the compound prepared in Synthesis Example 1.
비교예 1: 종래기술에 따른 유기전계발광소자의 제조Comparative Example 1: Fabrication of organic light emitting diode according to the prior art
본 발명의 화합물 대신에 9,10-디(2-나프틸)안트라센을 사용하였다는 점을 제외하고는, 상기 실시예 1과 동일한 방법에 따라서 유기전계발광소자를 제조하였다. An organic light emitting diode was manufactured according to the same method as Example 1 except for using 9,10-di (2-naphthyl) anthracene in place of the compound of the present invention.
하기 [표 1]에는 실시예 1, 2, 3, 4, 5, 6, 7 및 비교예 1에 따른 유기전계발광소자의 다양한 특성들을 정리하였다.Table 1 summarizes various characteristics of the organic light emitting display device according to Examples 1, 2, 3, 4, 5, 6, 7 and Comparative Example 1.
상기 [표 1]을 참조하면, 실시예 1 ~ 7에 따른 유기전계발광소자가 비교예 1에 따른 유기전계발광소자에 비해서 전력효율 및 발광효율이 우수하며, 장수명을 갖는다는 사실을 확인할 수 있다. 구체적으로 본 발명에 따른 유기전계발광소자의 경우 비교예의 경우에 비하여 수명이 최대 8배 이상 연장되며, 휘도는 2.5배 이상 향상되고 전류효율은 최대 2.5배, 전력효율은 최대 3배 이상 향상되는 매우 우수한 효과를 거둘 수 있다.Referring to [Table 1], it can be confirmed that the organic light emitting display device according to Examples 1 to 7 is superior in power efficiency and luminous efficiency and has a long life compared to the organic light emitting display device according to Comparative Example 1. . Specifically, in the case of the organic light emitting device according to the present invention, the lifespan is extended by at least 8 times as compared with the case of the comparative example, the luminance is improved by 2.5 times or more, the current efficiency by 2.5 times, and the power efficiency by 3 times or more. Excellent effect can be achieved.
도 1a~1e는 본 발명의 바람직한 실시예에 따른 유기전계발광소자들의 적층 구조를 나타낸 단면도들이다.1A to 1E are cross-sectional views illustrating stacked structures of organic light emitting diodes according to exemplary embodiments of the present invention.
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- 2009-02-11 KR KR1020090011010A patent/KR101092005B1/en active IP Right Grant
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