US 9,812,652 B2
Cyclic azine compound having adamantyl group, production method, and organic electroluminescent device containing it as constituent component
Nobumichi Arai, Kanagawa (JP); Keisuke Nomura, Kanagawa (JP); and Tsuyoshi Tanaka, Kanagawa (JP)
Assigned to TOSOH CORPORATION, Yamaguchi (JP)
Appl. No. 14/902,179
Filed by TOSOH CORPORATION, Yamaguchi (JP)
PCT Filed Jul. 8, 2014, PCT No. PCT/JP2014/068202
§ 371(c)(1), (2) Date Dec. 30, 2015,
PCT Pub. No. WO2015/005351, PCT Pub. Date Jan. 15, 2015.
Claims priority of application No. 2013-143909 (JP), filed on Jul. 9, 2013.
Prior Publication US 2016/0372678 A1, Dec. 22, 2016
Int. Cl. C07D 251/24 (2006.01); C07D 401/10 (2006.01); C07C 309/65 (2006.01); C09K 11/06 (2006.01); H01L 51/50 (2006.01); H05B 33/14 (2006.01); H01L 51/00 (2006.01); C07F 5/02 (2006.01); C07D 401/14 (2006.01); C07D 403/10 (2006.01); C07C 309/06 (2006.01)
CPC H01L 51/0067 (2013.01) [C07C 309/06 (2013.01); C07D 251/24 (2013.01); C07D 401/10 (2013.01); C07D 401/14 (2013.01); C07D 403/10 (2013.01); C07F 5/025 (2013.01); C09K 11/06 (2013.01); H01L 51/0052 (2013.01); H01L 51/0058 (2013.01); H01L 51/0072 (2013.01); C07C 2603/74 (2017.05); C09K 2211/1011 (2013.01); C09K 2211/1014 (2013.01); H01L 51/5056 (2013.01); H01L 51/5072 (2013.01)] 15 Claims
 
1. A cyclic azine compound represented by the formula (1):

OG Complex Work Unit Drawing
wherein Ad each independently represents a 1-adamantyl group (Ad1) or a 2-adamantyl group (Ad2):

OG Complex Work Unit Drawing
p and q are each independently 0 or 1,
Ar1 and Ara are each independently a single bond but only when p is 1 or q is 1, a C6-30 aromatic hydrocarbon group, which may have, as a substituent, a fluorine atom, a C1-4 alkyl group, a C6-18 aromatic hydrocarbon group, a C6-18 aromatic hydrocarbon group substituted by a fluorine atom, a C6-18 aromatic hydrocarbon group substituted by a C1-4 alkyl group, a C6-18 aromatic hydrocarbon group substituted by a C3-13 heteroaromatic group, a C3-13 heteroaromatic group, or a C3-13 heteroaromatic group substituted by a C1-4 alkyl group, or a pyridyl group which may be substituted by a phenyl group or a methyl group,
Ad groups on Ar1 and Ar3 are each independently bonded to said C6-30 aromatic hydrocarbon group or said pyridyl group,
Ar2 is each independently a C3-13 heteroaromatic group or a C6-18 aromatic hydrocarbon group, wherein these groups each independently may have, as a substituent, a fluorine atom, a C1-4 alkyl group, a C6-18 aromatic hydrocarbon group, a C6-18 aromatic hydrocarbon group substituted by a fluorine atom, a C6-18 aromatic hydrocarbon group substituted by a C1-4 alkyl group, a C6-18 aromatic hydrocarbon group substituted by a C3-13 heteroaromatic group, a C3-13 heteroaromatic group, or a C3-13 heteroaromatic group substituted by a C1-4 alkyl group,
X1, X2, X3 and X4 are each independently a single bond or a C4-14 arylene group, which may be substituted by a fluorine atom, a C1-4 alkyl group, a phenyl group, a biphenyl group or a naphthyl group,
m is 0, 1 or 2,
n is 0, 1 or 2,
Z is a nitrogen atom, and
n+p+q is 1, 2 or 3.